1990 年代のベストソング 250

By Pitchfork

One of the great joys of listening to music in the ’90s was then being able to curate your own best-ofs. It was the decade of cassette mixtapes, the highly personal, labor-intensive home recording projects that involved patiently waiting for a song to play on the radio in order to tape it, or painstakingly rewinding and fast-forwarding to an exact right moment to dub from one cassette to another. Writing out the tracklist and embellishing it with design was an entire artform in itself. This was the first version of personal playlisting. Here are the 250 songs that would make up Pitchfork's ultimate ’90s mixtape.

Read Pitchfork's list of the best albums of the 1990s here, and check out our full ’90s package here.

For more about how we put together this list, read this letter from our editor-in-chief Puja Patel.

Our 2003 list of the best albums of the 1990s can be found here. Our 2010 list of the best songs of the 1990s can be found here.

Work / Columbia

Of all the great one-hit wonders of the ’90s, Len's "Steal My Sunshine" might be the most enduring and the most inexplicable. Somehow, a pair of Canadian siblings managed to capture the essence of Southern California in a single that turned into a summertime perennial. The song comes into view slowly, like a mirage shimmering on the edge of a sun-bleached horizon. Its foundational sample of Andrea True Connection's disco classic "More, More, More" reveals itself as a grounding mantra, then the bliss goes widescreen once Len crash into the verse. Marc and Sharon Costanzo share a lackadaisical vocal affect—it sounds like they hit the studio directly after getting burned on the beach—but where so many slackers couldn't be bothered to shape their slothfulness into hooks, Len cares deeply about leisure: They’re committed to wasting away the hours that make up a dull day. Because nothing sounds better than doing absolutely nothing. –Stephen Thomas Erlewine

Listen: Len, "Steal My Sunshine"

Loud / RCA

No need to address Inspectah Deck's opening lines, which everyone who cares about the Wu-Tang Clan already knows by heart, and has probably tried rapping themselves at some point. They’re great, but they stick in your head above the others partly by virtue of coming first. What about Raekwon's white-gold tarantula, rhymed—unbelievably but perhaps inevitably—with "substantial-a"? Even U-God gets an all-timer in there, singing a song from Sing-Sing, sipping on ginseng. The monumental first single from their sprawling and uneven second album, "Triumph" is the Wu's last great stand as a nine-man team and one of hip-hop's greatest posse cuts. Over suitably dusty RZA production, with nothing remotely resembling a chorus, they go in for six minutes about Marvel comics and Mortal Kombat; Tennessee Williams and Laurel & Hardy; champagne bottles and squabbles with rival crews; and, of course, the will of the Wu to rule it all. They were never particularly aligned with commercial trends, but in 1997, at the dawn of the shiny suit era, this sort of wordy mythologizing was especially unfashionable. And yet, with no concessions to the mainstream save its blockbuster music video, it went platinum. The first line of the final verse provides the most apposite reaction: "Ayo, that's amazing." –Andy Cush

Listen: Wu-Tang Clan, "Triumph"

Righteous Babe

Ani DiFranco kicked off her studio discography with a mature song about the end of an affair that she recorded when she was just 18. The opening track off her self-titled debut, which was also the first release from her DIY label Righteous Babe, "Both Hands" hangs sensual recollections on a skeleton of trembling acoustic guitar. Flickering between a slam-poetry cadence and the frantic trill of a Gen X Joni Mitchell, the bisexual-icon-to-be narrated the dissolution of a formative relationship with a person of unspecified gender, whose physical contours read as female. It would take a few years for DiFranco to become the default soundtrack of coffeehouses and women's centers, but with "Both Hands"—still her most popular track—she arrived as both a throwback to folk's idealistic hippie heyday and a prophet of sexual revolutions to come. –Judy Berman

Listen: Ani DiFranco, "Both Hands"

Dischord

While colonizing the Americas in the 1700s, officers from Britain enacted biological warfare by intentionally gifting blankets infected with smallpox to Indigenous Americans. Though historians debate if the method even worked, it's a revolting act immortalized in the diaries of those who pulled it off—and the history lesson at the heart of In on the Kill Taker's most energizing track. Led by Guy Picciotto's fuming vocals, "Smallpox Champion" is a scathing condemnation of U.S. genocide filtered through Fugazi's rousing brand of post-hardcore. Between Brendan Canty's aggressive tom hits and Ian Mackaye's wiry guitar noise lies a protest song without any of the typical cliches or moral preaching. Instead, Picciotto delights in the promise of retribution: "History rears up to spit in your face." By the time its whammy-bar riffs ring out and its "cha-cha-cha" chants start, Fugazi sound almost joyful. "You’ll get yours," cheers Picciotto. "Woohoo-hoo!" –Nina Corcoran

Listen: Fugazi, "Smallpox Champion"

SBK

"Hold On" stitches together the camp and corniness left over from the ’80s, chintzy piano, and what should sound like affirmations stitched on throw pillows—open your heart and mind, tomorrow will be easier, you’re responsible for your own happiness—into a panoramic anthem. The track begins with a tingle of percussion and just the suggestion of strings before those schmaltzy chords chime in. Beneath the sweet sheath of harmonies and lilting melody, Wilson Phillips issue a command: just keep going. It's a plea packaged as a pep talk: "Hold On" was Wilson Phillips’ first single, and they needed the hit to slide out of their parents’ shadows (consisting of descendants of both Brian Wilson and the Mamas & the Papas, the band was soft-rock royalty). With "Hold On," they asked to be taken seriously, on their own terms—with the hope that you, too, could recognize your potential, even if only for one more day. –Dani Blum

Listen: Wilson Phillips, "Hold On"

Burning Heart

Refused get blamed for everything that came after their genre-exploding masterwork "New Noise": nu-metal, Hot Topic-core, rudimentary techno beats dropped casually into the breakdowns of hardcore songs. But what elevates this song above mere pastiche is its finely tuned balance. Here, the Swedish hardcore band is painfully self-serious, but also looser and more playful than most of their peers and imitators. Every part of the song does its job: The circuitous intro signals the arrival of something momentous, the verses build tension, and the choruses hit with meteoric force. With unwavering confidence, Refused promised a new sound and then actually delivered an opus that pointed a way forward for heavy music in the new millennium. –Mehan Jayasuriya

Listen: Refused, "New Noise"

Arista

Deborah Cox spent the first six months of her music career touring as a backup singer for Celine Dion, a crash course in how to make every note a spectacle. On her breakout hit, "Nobody's Supposed to be Here," the smallest shifts are mesmerizing—the jagged edge in her throat when she admits love has knocked her down, the way the vowel caves in when she sings the word "sad," the shock of shriek that builds up as she belts the chorus. Gentle percussion and chimes swirl in the background, and the song winds around and around Cox's circular thinking, as she spirals through dejection, hope, and refusal, all leading up to a cathartic key change. "I’m not supposed to care anymore," she moans as the track trickles out, a final sigh before she gives in. –Dani Blum

Listen: Deborah Cox, "Nobody's Supposed to Be Here"

DeSoto

By the time the Dismemberment Plan released Emergency & I, in 1999, the band didn't fit into any existing niche. Born from Washington, D.C.'s punk scene, they twitched around rhythms more like nervous jazzbos. Embraced by indie rock fans, their third album was bankrolled, and then ditched, by an easily distracted major label. Emo? Fine—but "You Are Invited," the record's affecting centerpiece, also did icy electronic drum throbs a year before Radiohead's "Idioteque," and witty post-punk speak-singing a cultural eon before LCD Soundsystem's "Losing My Edge." Its message, delivered by Travis Morrison with genial yearning, was simple: What if you got a sheet of paper guaranteeing you could never be left out of the party again? The uncanny similarity between the "since you’ve been gone" refrain on another great Emergency & I song, "The City," and Kelly Clarkson's subsequent smash hinted at D-Plan's potential to transcend boundaries of genre and scene; on a wide-eyed journey toward fist-pumping catharsis, "You Are Invited" embodies that welcoming generosity of spirit. It's an all-access pass to self-acceptance—and like the main character in the song, you’ll immediately want to pay it forward to the next person who needs it. –Marc Hogan

Listen: Dismemberment Plan, "You Are Invited"

Tommy Boy

Even the most ambitious spiritual lyrical miracle MC would be hard-pressed to match the pace of Treach's nimble tongue on "Feel Me Flow." Yet Naughty by Nature's missive feels less like a flex than a dare: Can you party as hard as they do? Atop a twinkling sample of the Meters’ "Find Yourself," this 1995 song-of-the-summer candidate finds Treach stuffing bars with rhymes and mocking the nerds who can't keep up. The East Orange, New Jersey rap group balanced their grit with a bit of goofiness (not unlike their Newark neighbor Redman), best evidenced by the accompanying music video, in which the whole hood is transported from summer on the block in Jersey to winter on the slopes in Vermont. –Matthew Ismael Ruiz

Listen: Naughty by Nature, "Feel Me Flow"

Ricochet / Ariola / BMG

Robyn Is Here was the name of the Swedish pop wunderkind's debut album, but could anyone have understood what a poignant and prophetic statement it would be? In the years to come, Robyn would recalibrate pop with her specific brand of shattered euphoria, songs that doused you in glitter even while seeping into your every ache. But as a teen hitmaker, she crash-landed on the U.S. charts with a handful of glinting, gooey singles. "Show Me Love" is a blast of Max Martin confection, with syrupy synths and the sugar rush of Robyn's belt in the chorus, trapping the burgeoning star in amber. –Dani Blum

Listen: Robyn, "Show Me Love"

Epic

The success of grunge presented a quandary for many of its practitioners; accustomed to marinating in the untested righteousness of their anticonsumerism, they now had to grapple with the fact that millions of consumers, among them fist-pumping jocks and radio-loving dilettantes, were now wholly into their stuff. No one suffered more openly on the horns of his stardom than Eddie Vedder, who took every available opportunity to minimize the uncritical worship his band inspired. He also made maybe the best entry in the canon of pop music by famous people about the wages of fame. Pearl Jam's "Corduroy," off the band's third album, Vitalogy, transcends the meager limits of the category by being irresistible about wanting to be resisted. Every move works here, from the tolling guitar arpeggios of the first few bars to Jeff Ament's prowling bass solo that I swear is an homage to Fleetwood Mac's "The Chain." "I don't want to take what you can give/I would rather starve than eat your bread," Vedder howls at his fans, but the hook undermines his attempt to distance himself from their affections. Fame's a bummer, the rock star laments, while the world can't help but hum along. –Tommy Craggs

Listen: Pearl Jam, "Corduroy"

Roc-A-Fella

JAY-Z's classic debut LP Reasonable Doubt sounds like little else in his catalog, with one foot planted firmly in the street and the other set to step into the boardroom. It's peppered with prominent entries into the rap canon, but few embody his capitalist gangster ethos better than "Dead Presidents II." The original version—released as a single ahead of the album—features the same gorgeous loop of the piano melody from Lonnie Liston Smith's "A Garden of Peace," but its juvenile braggadocio falls flat. The new verses on the album version exude a quieter confidence, with a tone more reflective of an underground kingpin assured of his future success. Of course, Jay's later claim that "You made it a hot line, I made it a hot song" about the Nas sample that serves as the chorus always seemed disingenuous, because "The World Is Yours" remains one of the defining works of the boom-bap era. But "Dead Presidents II" does evince one of the reasons JAY-Z has managed to maintain relevance as various trends explode and fade into the ether: A preternatural ability to borrow from others to make something truly his own. –Matthew Ismael Ruiz

Listen: JAY-Z, "Dead Presidents II"

Food

After charging through the football stadium in aimless elation, soundtracked to the sound of Damon Albarn's "WOO-HOO," Moe Szyslak turns to Homer Simpson and says, impatiently: "We’ve been running around cheering for an hour! Where the hell's the game?" The 1999 Simpsons bit perfectly taps into the spirit of Blur's atypically free-spirited "Song 2," a flippant yet propulsive FRAP of a track that can make grown men earnestly lose their shit before they realize they’ve been had. A parody of post-grunge American rock that was originally presented to their label as a joke, "Song 2" swept up the very market it was meant to be mocking. With its 12-beers-deep nonsense lyrics and car alarm power chords, the track—irresistible as it is—was ubiquitous during sporting events in the ’90s, signaling each touchdown and post-match celebration. May its capacity to cause male onset zoomies never wane. –Emma Madden

Listen: Blur, "Song 2"

San Jacinto

With singer Robin Wilson as his amplifier, Gin Blossoms’ core songwriter Doug Hopkins could wring honey out of his heart's most festering wounds. The Arizona rock band's signature hit lights up a last-ditch effort to claw back a lost love from the ruins of one's own mistakes. "If you don't expect too much from me/You might not be let down," Wilson sings, the words rippling out uncannily smooth, their inherent desperation buffed to a shine. The levity in the song's arrangement—the jangling guitar arpeggios, the shivers of tambourine—belie the weight of the addiction and mental illness Hopkins found himself tangled in while writing, which dragged him to his death a few months after "Hey Jealousy" got a foothold on the pop charts. But the lyrics hide nothing, their abyssal despair and fevered hope laid bare in the curl of a perfect hook. –Sasha Geffen

Listen: Gin Blossoms, "Hey Jealousy"

Warp

Every moment of "Echo's Answer" feels like it is falling in and out of focus. It is a tone and mood befitting Broadcast, a band that was born from ’60s club nights in their native Birmingham, England and grew within a UK scene anchored by similarly psychedelic pop groups like Stereolab and Pram. Broadcast distinguished themselves through dub-like production techniques and jazzy drumming that made their work as slippery and mysterious as the undulating wax in a lava lamp. On this track, though, even the most solid component of the band's work, the enchanting vocals of the late Trish Keenan, vanishes in the haze with lyrics that elude easy interpretation and a post-production effect that swallows her last line into a wormhole. The only appropriate course of action is to follow her down. –Robert Ham

Listen: Broadcast, "Echo's Answer"

Elektra

In 1988, Tracy Chapman's influential self-titled album and breakthrough "Fast Car" presaged the folk revival to come. Yet throughout the ’90s, critics called her music "dour," never truly grasping the complexity with which Chapman integrated stories of disenfranchisement and poverty alongside her gently melodic love songs. On 1995's New Beginning, Chapman found her second wind through an album that brightened the corners of her folk music with an eye toward renewal and environmentalism (the CD even came bundled with a coupon for a packet of seeds to be redeemed at her shows). "Give Me One Reason" is the record's bluesy highlight and her biggest hit to date, strutting along a plucked, head-nodding guitar melody and Chapman's grainy alto. Centering on an imbalanced relationship, each verse grows more frustrated from a lack of reciprocity; then the band kicks in and the pleading in her voice becomes cathartic, begging for a reason to stay while knowing it won't come. The bittersweet ultimatum seemed to bloom out of years of romantic frustration, but in Chapman's voice and arrangement it becomes a balm, guiding listeners through the push and pull of loving someone who can't give you what you need. –Eric Torres

Listen: Tracy Chapman, "Give Me One Reason"

Immortal / Epic

Jonathan Davis knew he was trapped. The Bakersfield misfits of Korn were becoming the outlandish stars of ascendant nu-metal, so to make their third album, they tapped endless industry spoils: a recording budget nearing a million, a ceaseless stream of booze and blow, a vocal coach literally punching Davis in the back. But he also bristled at sudden commodity status, knowing free stuff wasn't actually freedom. "Freak on a Leash" is the sound of pariahs pounding against asylum walls, of demanding to be let out despite being permanent hostages, "a cheap fuck for me to lay." Those pinprick guitars are tin snips taken to barbed wire, that lashing rhythm section a sledgehammer against an armored door. The dangerous assault, though, comes after two minutes, with the era's most unhinged vocal paroxysm—Davis’ beat-boxed glossolalia, 27 terrifying, cathartic, and sort of hilarious seconds where frustration overruns the capacity of language. When Davis commands "Go!" imagine yourself rushing the gates, too, outrunning bullets at your back. –Grayson Haver Currin

Listen: Korn, "Freak on a Leash"

Ruffhouse / Columbia

The B-side to Cypress Hill's debut single "The Phuncky Feel One," this West Coast anthem was much of the world's introduction to the bong-toking cholos that would help define the gangsta rap sounds coming out of Southern California in the early ’90s. With boom-bap drums punctuated by the squeal of sampled horns, "How I Could Just Kill A Man" is the battle cry of disaffected youth driven to meet violence with violence. In some ways it sits on other side of the same coin as Ice Cube's "It Was a Good Day"; where Cube's good fortune guides him away from the gaze of corrupt cops and carjackers, B-Real faces it head-on, dismissing detractors who could never understand the daily dangers he faces. "So how do you know where I'm at, when you haven't been where I've been?" he asks, already knowing the answer: It's easy to declare violence is not the solution when you never have to face it. –Matthew Ismael Ruiz

Listen: Cypress Hill, "How I Could Just Kill a Man"

Opal / Warner Bros.

Like the best art from devotional poets John Milton or John Donne, one of Brian Eno's masterworks is a hymnal from a funny angle—not upward, from man to his unknowable God, but southward, from its point of view back down. "I am the wheel," Eno drones sunnily, in a pop song that sounds aerially suspended. "I am the turning."

Maybe this beatific rush was a product of Eno's somewhat fighty relationship with collaborator John Cale; maybe it was shaped out of the runoff from the semi-liquid ambient classic Thursday Afternoon, released five years before it; or maybe just from a random pang of bliss in the long wake of his emancipation from Roxy Music. Who's to say. A single card from Eno's Oblique Strategies deck of creative prompts might be most explanatory of "Lay Your Love"'s magic, monkish kiss to and from the divine. It bears one word against a white void: "Courage!" –Mina Tavakoli

Listen: Brian Eno / John Cale, "Lay My Love"

Virgin

Jim Steinman, the mad genius who wrote "It's All Coming Back to Me Now," said he was inspired by the novel Wuthering Heights, and compared it to "Heathcliff digging up Cathy's corpse and dancing with it in the cold moonlight." This is important to remember, because there is no scene in Wuthering Heights where Heathcliff digs up Cathy's corpse and dances with it in the cold moonlight. But this haunted and windswept romantic fantasia is what's conjured by Celine Dion's spirit-galvanizing rendition of Steinman's song. Dion, the most successful balladeer of the ’90s, summons all the power in her soul and lungs to commune with the dead, the theatrically proggy arrangement crescendoing behind her. She sings about making love so intense it's banned by the law; she's joined by a reassuring chorus who agree, yes, that feeling she remembers is coming back to her now, Dion isn't just making this up. Her passion hits an apex as she sings "baby, baby, baby" like she's squeezing her hand through a tight space to reach the afterlife. It's the stuff of romance novels, even if it never literally happened in one. –Jeremy Gordon

Listen: Céline Dion, "It's All Coming Back to Me Now"

Wiiija

In 2011, Asha Bhosle recalled the time that "Brimful of Asha" helped her through the immigration desk at London's Heathrow Airport. When the officer on the desk quizzed her on her profession as singer, she offered the silky, languorous indie-pop Cornershop song as a reference—not because it was one of the thousands she’d appeared on over her years as a Bollywood playback singer, but rather because it was one written in her honor. By then—thanks mostly to a pitched-up earworm of a big-beat-era Fatboy Slim remix—the song was a core component of rose-tinted nostalgia for the late ’90s. For a song about recognition—fighting for it, or being denied it—by a political, punkish, Punjabi-led band who’d named themselves after the racial stereotype of British Asians owning convenience stores, Bhosle's immigration play was perhaps a fitting encounter. After all, in Hindi, the name Asha also means "hope." –Will Pritchard

Listen: Cornershop, "Brimful of Asha"

Motown

Was life really ever as earnest and pure as Boyz II Men's "Motownphilly" music video made it out to be? In 1991, when the fledgling Philly group released its first single, it was all youthful exuberance spilling out in oversized pink blazers, matching bow ties, and snazzy horn riffs. (Also: If Tik Tok teens haven't studied this choreography yet, they are missing out.) Michael Bivins of New Edition and Bell Biv DeVoe appeared on the track, which features classic soul harmonies over a new jack swing beat, as well as a totally gratuitous doo-wop showcase at the end. Not too hard and not too soft, the song ushered in the decade of copycat (and largely whitewashed) boy bands that would follow. –Emma Carmichael

Listen: Boyz II Men, "Motownphilly"

A&M

NASA recently shared what a black hole really sounds like, and it turns out that Soundgarden wasn't so far off. Summer anthems are rarely as dark as night, but for a band drenched in Seattle's stormy ethos, it's fitting that their biggest hit was this masterfully trippy power-dirge. Sporting a famous video full of apocalyptic suburbanites with over-sized eyes, "Black Hole Sun" begins with dreamlike guitars and Chris Cornell in full croon. Eeriness immediately invades, before the crunch of Cornell and Kim Thayil's drop D guitars drive everything further down the rabbit hole. "Heaven send hell away," Cornell pleads, "No one sings like you anymore." The sentiment resonated all the more as it blasted from radios at the crest of the Seattle rock wave, just months after Kurt Cobain died. –Jessica Letkemann

Listen: Soundgarden, "Black Hole Sun"

LaFace

Just because Goodie Mob were paranoid didn't mean people weren't following them. While this ad-hoc crew of OutKast affiliates had never recorded a song together before the sessions that would become 1995's Soul Food, their debut album's bone-chilling hit laid out a lasting template for how Southern hip-hop could be at once conscious and crunk. "Cell Therapy" was both menacing and menaced, fucked up by conspiracy theories but also the conspiratorial realities of systemic racism. Its gutturally drawled, often-surreal vision of life near the trap would be familiar to Atlanta viewers, let alone EarthGang or Denzel Curry listeners, and its eerie, dub-cavernous production also set a course so irresistible that it was echoed by Gorillaz and sampled by Travis Scott. But the song's most resonant association is the moment it soundtracks in Barry Jenkins’ classic 2016 film Moonlight: Our now full-grown hero wakes from a nightmare, looking tough as nails, scarred within by trauma that's deeper than the red Georgia clay. –Marc Hogan

Listen: Goodie Mob, "Cell Therapy"

Columbia

The darkness underneath "Would?" has belied its tenure as a rock radio staple since its release in 1992. Layne Staley wrote the song about Andrew Wood, the lead singer of fellow grunge band Mother Love Bone, who died of an overdose in 1990. All that pain and grief funnels into the song's final minute, which also happens to be the final minute of Dirt, Alice in Chains’ hour-long march through a fetid Seattle carnival of depression, suicide, and heroin. Staley does a kind of whammy bar dive-bomb effect on his voice on "mista-a-a-a-ke" before unveiling its upper register; drummer Sean Kinney gets a nice fill showcase; the band ends on a unison five-note rubato car honk: "If I would, could you?" The question "Would?" asks becomes hellaciously macabre in light of Staley's overdose death in 2002, but the song stands as a long-lasting totem of the Seattle scene's heavy sound and heavier struggles. –Jeremy D. Larson

Listen: Alice in Chains, "Would?"

Atlantic

Jawbox's "Savory" was one of the unlikeliest alt-rock crossover bids of 1994. Instead of gambling on the tidy production style that decided many a punk band's fate at the time, the Dischord expats drilled deeper into their fiery essence for the first single off their major label debut. Propelled by an evil swing with dangerous riptides underneath, the song keeps things tense even in the tuneful chorus. Though "Savory" aired on MTV's 120 Minutes and Beavis and Butt-Head, its blunted serration skidded off the mainstream, and the band's deadpan mien and newfound penchant for formal dress didn't make their cryptic music any more accessible. But those same intractable qualities set the song apart as one of the heaviest, grooviest, most soulful post-hardcore anthems ever. –Brian Howe

Listen: Jawbox, "Savory"

Noo Trybe

Did Luniz always intend "I Got 5 on It" to sound so sinister? The Bay Area rap duo wrote the song, their lone hit, about going 50-50 on a dime bag, and on paper it's a celebration of the rituals and etiquette of social smoking. But the musky, nocturnal beat, built from a corroded sample of R&B group Club Nouveau's late ‘80s hit "Why You Treat Me So Bad," turned the track into an exercise in paranoia. It wasn't a stretch, then, when Jordan Peele absorbed the track into the score for his 2019 horror movie Us. The raps invite you to chip in; the beat cautions you to beware. –Evan Rytlewski

Listen: Luniz, "I Got 5 on It"

Go! Discs

Sometimes credited as the opening salvo of Britpop—Noel Gallagher once declared it his favorite song of the ’90s—this delicious single certainly owes poetic debt to the Velvet Underground's "There She Goes Again." On first listen it sounds like a lost ’60s classic stripped to the beams, just an indelibly repeated chorus with sly variations over Byrdsian guitar chime. The melody, parsed out over a seven-word juggling of the title, is irresistible; the jangling riffs appeal to a cultural sweet tooth that the Smiths’ Johnny Marr and R.E.M.'s Peter Buck reawakened in the ’80s. The lyrics play with the classic love-is-the-drug metaphor so expertly that the song joined the ranks of alleged pop paeans to heroin while simultaneously inviting an excellent cover by Christian alt-rock charmers Sixpence None the Richer. It's a perfect earworm that leaves its parting strum unresolved just enough to make you want—need—to hear it again. –Will Hermes

Listen: The La's, "There She Goes"

Tommy Boy

An entire drag ecosystem earning a small country's GDP would simply not exist without RuPaul's 1992 single, which ushered in a catchphrase that, 30 years later, lives on in the Drag Race multiverse: "Sashay, shantay." A club queen who’d frequented New York's most storied downtown establishments (and the Shaque D’Amour) and established herself as a beloved weirdo in a scene full of them, Ru's runway-empowerment house track got heavy rotation on MTV when such things still mattered, becoming a mainstream hit in an underdog-friendly year. (Kurt Cobain loved this song, resulting in the iconic photo of Ru and her skyscraper beehive holding a crying Francis Bean at the ’93 VMAs.) Ru was a 6’4 drag queen cheekily instructing listeners to "make love to the camera," but it didn't read as a novelty. It was a perfect pop song for the supermodel era, and one that launched a thousand drag careers, with mother Ru and her bigass wig at the forefront, catwalking the filthy streets of ’90s NYC. –Julianne Escobedo Shepherd

Listen: RuPaul, "Supermodel (You Better Work)"

Minty Fresh

The version of you who scrawls venomous graffiti on bathroom walls, who claps back at bullies, who keeps a running hit list and lies awake plotting revenge? She is the Seether, the alter-ego antihero in the song that took Chicago four-piece Veruca Salt from alt-rock obscurity to the main stage of Glastonbury in just a year. "Seether" is bubblegrunge at its finest, all guitar fuzz and pop stickiness and crackling angst animating a personification of anger that just can't be leashed. "I try to cram her back in my mouth," co-frontwoman Nina Gordon sings in the verse, but she didn't really try that hard. The Seether is everywhere, most recently on the lips of Olivia Rodrigo and fans who discovered the song through her live cover—a new generation blessed with a soundtrack for their righteous rage. –Olivia Horn

Listen: Veruca Salt, "Seether"

Food

The nu-disco lead single from Blur's Parklife, "Girls & Boys" might have been a sonic outlier in their ambitious catalog, but it was quintessentially Blur in its pithy observations of middle-class English culture. "It's the travels of the mystical lager-eater," Damon Albarn said of his inspiration: an Essex bloke en vacance, sunburned and stumbling through Majorca nightclubs. "Girls & Boys" remains one of the finest examples of a rock band crossing over into dance music, thanks largely to Alex James’ buoyant bassline and Graham Coxon's assertively sour guitar work, which provided the tart top note in an otherwise candy-coated banger. His dissonance mimicked Albarn's paradise, plagued by bad omens like paranoid love and looming unemployment. Is this a holiday—or sun-drenched hell? –Madison Bloom

Listen: Blur, "Girls & Boys"

Sony Music Latin

In 1998, merengue was on its last legs in the Latin music market—until Puerto Rican vocalist Elvis Crespo came along and dropped the surprise smash hit "Suavemente." Since then, there's absolutely no way you’ll attend any Latino cookout, wedding, or party without watching everyone run out of their seats to the dancefloor once the opening a cappella—"Suavemente, Bésame/Yo quiero sentir tus labios" or "Kiss me softly, I want to feel your lips"—hits, before exploding into horns, güira, and percussion that feels like unending swooning euphoria. "Suavemente" gave merengue its glorious breakthrough for mainstream audiences; while it may not be the biggest Latin hit of the ’90s, there are few that remain as beloved and feel-good romantic to your tias. –Gio Santiago

Listen: Elvis Crespo, "Suavemente"

Elektra

There's a sneering swagger to the way Third Eye Blind sang about disaffection and apathy on their debut single, "Semi-Charmed Life." They were losers like Beck but combative about it, as if to say: Gaze upon us, ye professional managerial class, and despair. Nestled within the sunshine guitar riff and the "doot doot doot" harmonies borrowed from Lou Reed was a cautionary tale about crystal meth addiction, and falling into a lifestyle that sucks up the years before you realize they’re gone. Seemed bad, but on the other hand: doot doot doot, doot doot-doot doot. It was the rollicking Clinton years, the end of history, and "Semi-Charmed Life" was big-tent solipsism for a generation of dirtbags and college graduates wondering "is this it?" as they navigated adulthood during a period of halcyon global stability. Well, we know what came next. –Jeremy Gordon

Listen: Third Eye Blind, "Semi-Charmed Life"

Motown

That doo-doo-doo-doo refrain: a starburst melody that simultaneously feels like it must have always existed and was surely beamed to Shanice from the heavens in a moment of celestial magic. "I Love Your Smile" is all about young romance and the joy that uncontrollably bursts from your chest cavity. Funky drums and a prominent bassline adds a streetwise undercurrent to the singer's effervescence. Though the radio edit foolishly omits Shanice's rap verse, her rudimentary rhymes attest to feelings of doubt, with the sound of thunder bringing a sudden seriousness to her voice. But then she releases the tension with a laugh, making way for a sax solo by none other than Branford Marsalis, the sun bursting through the clouds once more. –Dean Van Nguyen

Listen: Shanice, "I Love Your Smile"

MCA / Cargo

Blink-182 wrote dozens of songs about being teenagers, so it's ironic that the most enduring is also the most mature. The San Diego trio was riding the tide of local fame when this quintessential ode to growing up came out; within a couple of years, it had vaulted them into the Billboard Hot 100 and late-night TV. Its iconic guitar riff begins by simply moving up the major scale—about as rudimentary as it gets, but thematically perfect for a song about the travails of growing past childhood—with a tempo just fast enough to provide an actual challenge for all the kids it inspired to pick up the instrument. With "Dammit," Blink-182 evolved from their juvenile skate-punk origins to a (slightly) more grown-up sound, worthy of the radio domination that would soon come. –Nina Corcoran

Listen: Blink-182, "Dammit"

Interscope

After almost single-handedly reshaping the course of pop music as the pioneer of New Jack Swing in the late ’80s, singer-songwriter-producer Teddy Riley led his group Blackstreet to a career peak with this 1996 party anthem. One of the stickiest hip-hop/R&B hybrids of all time, "No Diggity" is so stacked with pleading, arm-waving pleasures that a stingier producer probably could have partitioned it out into three or four distinct hits. Along with that melodic abundance, the track heaves one larger-than-life voice on top of the next: Dr. Dre's linebacker huff, Chauncey "Black" Hannibal's chesty croon ("SHEEEE’S got class AND STYLE"), and an acrobatic verse from rapper Queen Pen. A nodding Bill Withers sample hangs over it all, like the voice of God himself looking down approvingly on this ridiculously good time. –Evan Rytlewski

Listen: Blackstreet, "No Diggity" [ft. Dr. Dre and Queen Pen]

Almo

When he wasn't stewarding Nirvana's Nevermind, enigmatic producer Butch Vig spent the first half of the ’90s stripping pop for parts, reworking songs by Nine Inch Nails, EMF, and Depeche Mode and leaving just their core vocals intact. Perhaps it's unsurprising that when Vig endeavored to condense his pop philosophies into a new venture, he had everything he needed for a hit with "Stupid Girl"—a drum sample ripped from the Clash, guitars pumped through a grab bag of effects, a bassline that flirted with the blues—except a vocalist.

Shirley Manson didn't just fill the void; on "Stupid Girl," the Scottish singer stared into it and sneered. Manson's low register added a seductive and soulful element to the surgical studio glean of Garbage's production, but she also, crucially, added a deadpan simplicity as a lyricist. Was "Stupid Girl" a diss track? Was it empowering? Was it even about a girl? Manson coyly avoided obvious answers, but the tremble in her voice on the final bridge hints that it could just as well be about the woman singing it. –Arielle Gordon

Listen: Garbage, "Stupid Girl"

Undeas / Big Beat / Atlantic

Lil’ Kim arrived in 1995 as the most colorful member of Biggie's Junior M.A.F.I.A., multitasking as the mistress, sexual deviant, and superstar in the crew. Her debut album Hard Core is a complicated declaration of freedom, and "Big Momma Thang" is Kim activating all of her multitudes: filthy, tough, conceited. The minute she spit the first line—"I used to be scared of the dick/Now I throw lips to the shit"—it opened up a wormhole to an explicit world for women both inside and outside hip-hop. The rest of the song, two verses spliced with a few meddlesome Jay-Z bars, is a PSA about her hopes and dreams, including 24 orgasms and carats, and ultimately her worth. –Clover Hope

Listen: Lil’ Kim, "Big Momma Thang"

Interscope / Atlantic

Built around a vocal performance so huge that it nearly swallows the song's jangly guitar riff, "What's Up?" is the sound of wild mood swings happening in real time. Frontwoman Linda Perry sang about being 25, exhausted by the pain of everyday living, and frustrated by the slow pace of personal and political progress, with the sincerity of someone young enough to keep striving for something better. Impossible to slot neatly into a genre, the track threw Perry into conflict with veteran producer David Tickle—who tried to rewrite her lyrics, among other unnecessary interventions—and forced her to fight for the eclectic, eccentric voice that would make her a sought-after pop songwriter in the aughts. The song is essential not just to Perry's origin story, but also to creating an overwhelming—perhaps chemically altered—rush of emotion that has fueled three decades of crying jags and karaoke jams. –Judy Berman

Listen: 4 Non Blondes, "What's Up?"

Arista

By the time Whitney Houston's rendition of the Chaka Khan anthem "I’m Every Woman" dropped, she was already an international star racking up countless awards, sold-out venues on world tours, and solidifying her spot as one of the greatest vocalists of all time. As a musician, she was on top of the world, which made her first foray into film all the more precarious. The Bodyguard wasn't exactly a cinematic breakthrough, but it produced the most successful soundtrack of any movie ever, and the ease with which Houston carried its classic banger immediately revived its anthemic status. Pulling out the disco that underlined the Chaka Khan original, Houston's version brings us to church, soft and welcoming, as her voice carries us for the first full minute before the beat drops. Walk into any nightclub, drag show, or karaoke bar (should you dare), and euphoria will take over the room should this song come on, lifting us up. At that moment, we are every woman. –Samhita Mukhopadhyay

Listen: Whitney Houston, "I’m Every Woman"

A&M

Pearl Jam didn't even exist when Soundgarden's Chris Cornell beckoned Eddie Vedder to duet on this plaintive power ballad, but what began as Cornell's unfinished elegy for fallen Mother Love Bone singer Andrew Wood came to crown the accidental Seattle supergroup led by members of two of the scene's biggest bands. Beyond its quintessential Seattle sound—especially those gentle-to-crunchy guitars, courtesy of nascent Pearl Jammers Mike McCready and Stone Gossard—the call-and-response of Cornell's multi-octave roar and Vedder's distinctive bari-tenor echoing the same lines over and over elevated the track into a classic. Incredibly, Vedder first stepped up to Cornell's mic to belt this one out during his week-long Pearl Jam audition in the rehearsal space the then-forming band shared with Temple of the Dog. Spoiler: Vedder got the job. –Jessica Letkemann

Listen: Temple of the Dog, "Hunger Strike"

KLF Communications

Residing cozily among Nelson and New Kids on the Block singles, house tracks manufactured by hook-savvy British and European producers made early 1990s pop radio a less traumatic experience. British stadium-house pranksters Jimmy Cauty and Bill Drummond conceived "3 a.m. Eternal" as a rap-conversant and club-designed worldwide smush; the title parenthetical, another of their knee-slappers, refers to the desk at which Cauty and Drummond mixed this not-live-in-the-slightest track. Yet "3 a.m. Eternal" generates the endorphin rush of a good concert experience and a better dose of MDMA. Besides its walloping rhythm, double-reed oboe solo, and creamy pre-chorus, it hurls spitballs like "bass ballistics" and "sample city through Trancentral," not to mention the useful maxim "time is eternal." What many who made "3 a.m. Eternal" a Top 5 hit remember, though, are the chant—"KLF is gonna ROCK YA!"—and a four-note bleep-hook tapped out on one of those period brick cell phones. Not many Euro-house tracks sported one of those. –Alfred Soto

Listen: The KLF, "3 a.m. Eternal (Live at the S.S.L.)"

Sire / Reprise

By the early 1990s, a decade as a second-string guitarist-songwriter for Throwing Muses and three parallel years in the Breeders still hadn't brought out the full range of Tanya Donelly's talent for tweaking Gothic cliches about madwomen in attics. Using demos she had initially prepared for a second Breeders album, she formed Belly, a group that could pivot from twinkling, sugar-spun ballads to impressively muscular power pop. "Feed the Tree," released in early 1993 after months of buzz, takes advantage of Donelly's talent for punching holes in the wall with a killer chorus. Tom Gorman's serpentine riff coils around the verses while bassist Fred Abong and drummer Chris Gorman keep their rhythms flippy-floppy. The result: an unexpected hit, gold-certified album, and Grammy nomination in a year when major-label moguls polished their glasses and studied those weird-ass little "modern rock" bands. Take your hats off, boys! –Alfred Soto

Listen: Belly, "Feed the Tree"

Creation

Some of the best power-pop songs are about the feeling of being turned on by music itself as much as any romantic interest: Big Star's "Thirteen" looked back on "Paint It, Black," and the Replacements’ "Alex Chilton" paid homage to the titular Big Star frontman. "The Concept," the misty and melancholic opening song from Teenage Fanclub's breakthrough record Bandwagonesque, starts out describing a denim-clad girl who buys records by Status Quo, an obscure ’60s group. By the fist-pumping coda—a marvel of searing guitars, bombastic drums, and wistful three-part harmonies—it's clear that frontman Norman Blake isn't in love with the girl so much as he relishes the idea of being in the band onstage, basking in the glow of raised lighters. It's a fantasy that Teenage Fanclub in some sense made real—Bandwagonesque famously beat out Nirvana's Nevermind on SPIN's best albums of the year list—and it exists anew every time someone plugs into power-pop's nostalgic charge. –Marc Hogan

Listen: Teenage Fanclub, "The Concept"

WEA / Atlantic

In hindsight, there's a slight irony to the massive success of "Return of the Mack," given that Mark Morrison was never quite able to capitalize on his deliciously petty signature song: It's a return in search of a departure, a comeback without a debut. In the years that followed his smash hit, a slick and triumphant British Invasion of the American R&B charts with a heavy ragga-tinged beat, Morrison's career would implode due to constant legal troubles—most infamously the time he hired a lookalike to do his court-mandated community service while he went on tour. The resentment and bitterness exemplified by his lone hit might have been Morrison's undoing when it came to career longevity, but "Return of the Mack" spins negativity into cathartic gold, a walking-on-air anthem designed to be played on repeat during those times when you need to manifest sweet comeuppance into reality. –Nadine Smith

Listen: Mark Morrison, "Return of the Mack"

MCA

No other ’90s artifact about selling out has endured like "You Get What You Give." New Radicals leader Gregg Alexander yelped about sticking it to the man, trashing cars, and disrespecting his retail premises, all to the kind of peak CD-era pop-rock that fattened the man's wallet and made U2 jealous. It's survived because there's not a drop of cynicism in it. Alexander considers the communal joy of forging an alternative, sung with irrepressible certainty that you are the antidote. The euphoric hit was too pure for this world and only grows more poignant in time: A disillusioned Alexander split up the band one single later, war broke out, and it turned out there was, allegedly, more than enough reason to want to kick Marilyn Manson's ass in. But for the four-and-a-half minutes of this song—which, by the way, once inspired a defeated Joni Mitchell to keep making music—the dreamer's disease still rages beautifully. –Laura Snapes

Listen: New Radicals, "You Get What You Give"

So So Def

Da Brat's swift ’90s rise is the stuff of hip-hop fairy tales. After winning a rap competition hosted by MTV, the young Chicago MC met producer Jermaine Dupri, inked a record deal, and began work on her debut album. She dropped the title track in May of ’94; by summer's end, it had peaked at No. 6 on the Billboard Hot 100. Bumping to a sample of the Isley Brothers’ baby-maker "Between the Sheets," "Funkdafied" wrapped Da Brat's jabbing, sassy flow in synthesized strings and a slinking bassline. The single baptized Da "Brat-tat-tat-tat" as a trailblazer—a bar-spitting tomboy who resisted the industry's appetite for more sexualized packaging. As "Funkdafied" cruised the airwaves, she became the first solo female rapper to go platinum. "I’m on a roll in control like Janet," she snaps in the third verse—her nod to royalty as she snatched her own crown. –Madison Bloom

Listen: Da Brat, "Funkdafied"

Matador

You could spend a lifetime trying to detangle the spell cast by "Cross Bones Style," with its twilit guitars and peppy percussion that never quite falls in step with Chan Marshall's voice. Searching for some kind of impossible salvation in the eyes of a child who has seen too much, her vocals are doubled—weary yet hopeful, meditative and pleading—like a rope that braids and frays. Cat Power's songs have protested the cruelties we inflict on each other; yet the abstracted poetry of "Cross Bones Style," inspired by two orphans whose parents were killed in South Africa's blood diamond mines, is both frighteningly specific and lingers like a myth. –Owen Myers

Listen: Cat Power, "Cross Bones Style"

Rawkus

The genius of producer Ayatollah's flip of Aretha Franklin's "One Step Ahead" is twofold: The sampled song's lyrics speak directly to the conundrum Mos Def (now known as Yasiin Bey) writes about on "Ms. Fat Booty," and it's also conceivably the record playing on the jukebox when the object of Mos’ affection blows him off during their first meeting. This is the rare love song that ends not in bliss or heartbreak but with the speaker's deflating realization that he simply can't keep up. The spark of recognition and last-call conspiracy gives way to an infatuation that consumes him but ebbs for her, made all the worse by the fact that you can see it from the front. –Paul A. Thompson

Listen: Mos Def: "Ms. Fat Booty"

DGC

On "Doll Parts," singer, guitarist, and songwriter Courtney Love dissects herself into slivers. Fake eyes, legs, and arms all fall at odd angles, their connective elastic snapped. When some men want women, they divide them in this way: reduce them to anatomical segments, seize upon a part, and throw away the rest.

Fame can do this to a person, too, a fact that Love knew well by the time Hole released their second album, Live Through This. In the years since the raw smolder of the band's 1991 debut, Pretty on the Inside, she had become half of a globally surveilled couple alongside Nirvana's Kurt Cobain, been the subject of multiple media scandals, and felt the scathing, desirous gaze the world casts on a woman who won't fit any of its molds. With "Doll Parts," Love crawls inside that mangling hunger and inverts it. She turns herself into plaster and then ignites the replica with her want. In pieces, charred and deformed, she begs to swallow the world, to make it feel the same pain that's accumulated for decades in her gut. –Sasha Geffen

Listen: Hole, "Doll Parts"

Columbia

Is Maxwell talking about love on "Ascension (Don't Ever Wonder)," the second single from Maxwell's Urban Hang Suite? A woman? God? Drugs? Maybe all of the above, which is why the chorus penetrates your soul: You know the feeling when something takes you to a place you’ve never been before. The album sequencing suggested it was about the throbbing crescendo of intimate and sexual love, which didn't stop the song from being beloved by church choirs—it is, after all, a Biblical reference. The track evokes an ethereal lightness, an angelic warmth that hugs you and elevates you higher, above yourself, to a new tier of consciousness. –Samhita Mukhopadhyay

Listen: Maxwell, "Ascension (Don't Ever Wonder)"

Matador

On the surface, "Pat's Trick" is an index of mid-’90s slacker-rock tropes: that chunky, rickety groove; that low-slung and loose-stringed sound; those tinny harmonies; and the countenance of bored contempt that singer-guitarist Mary Timony wears in the video. But the wonderful strangeness of her music can't help but glow through.

The lead single from Helium's Matador debut The Dirt of Luck, "Pat's Trick" is as mysterious a creature as the one silhouetted in its lyrics. The riffs and words are both squirmy and stunted, surging with the power of change. Too cool to raise her voice, Timony spread it over blistered crags of guitar and slashes of thick bass chords. It's the most accessible portal into Helium's thorned, enchanted world. –Brian Howe

Listen: Helium, "Pat's Trick"

Production House

These indelible slices of 1992 hardcore—in the breakbeat sense—build on a delirious premise delivered in chipmunk falsetto. The repeated vocal snippet expresses the foundational rave desire to be taken higher, perhaps by then-nascent smart drugs, perhaps to the title's heavenly body. ("Pt. 1"'s whirligig ending suggests UFO involvement.) One thing's for sure: The voice itself couldn't rise an iota further before slipping beyond human hearing. It pushes at intelligibility much as the track pushes past any semblance of early-’90s pop normalcy. This is a raucous blender montage of samples and effects, the beat a comforting throughline amid candy-colored chaos. Cinematic samples decorate riotous percussion, taking occasional breaks for proto-drop near-silences. "Pt. 2" is downtempo only by comparison: drums deeper, pace considered, vocals sodden from exertion. A trip to the moon means going up, but at some point you gotta land. Acen eases us down. –Marc Weidenbaum

Listen: Acen, "Trip II the Moon (Pt. 1 and 2)"

Slash

In 1991, outraged by Reagan and Bush Sr.'s years of attacks on reproductive freedom and galvanized by Anita Hill's testimony against Clarence Thomas, the L.A. punk band L7 co-founded Rock for Choice, a benefit concert series raising money for abortion rights groups. (Over the course of the following 13 years, Rock for Choice would feature almost every major alt-rock band, from Nirvana to Rage Against the Machine to No Doubt, and raise hundreds of thousands of dollars.) The following year, L7 released "Pretend We’re Dead," a protest anthem that bottled their activist spirit into four minutes of grunge perfection. Singer-guitarist Donita Sparks warned against the danger of political apathy over riffs as heavy as bricks; the only way forward was to "turn the tables with our unity," she beckoned. Thirty years later, the consequences of that unheeded warning are catastrophic beyond anything L7 could have imagined. –Amy Phillips

Listen: L7, "Pretend We’re Dead"

Work / Columbia

Released when she was 18 years old, the first song on Fiona Apple's debut album is a mature and clear-eyed statement of self-determination—whether you read it as a breakup song or a preemptive, prescient rejoinder to the small minds who would willfully misunderstand her in the early years of her career. Unlike the rest of Tidal's piano-forward tracks, "Sleep to Dream" builds from the beat up, a rumble anchoring Apple as she spits bars, her words so sharp and precise they could have been written with a scalpel. "I’ve got my own hell to raise," is her proclamation in the chorus. Through formal innovations and radical forthrightness, she has spent the decades since fulfilling that prophecy. –Olivia Horn

Listen: Fiona Apple, "Sleep to Dream"

One Little Independent

Not to get all What Women Want about it, but it's hardly surprising that the idealized male figure Björk rhapsodizes about in "Venus as a Boy" is described in terms of how he makes the narrator feel, and not what he looks like. This is beauty, according to Björk: attentiveness, the capability of making one's partner feel beautiful, and an apparent willingness to go down on her. She's not excited by his biceps or the bulge in his pants, but his sense of humor. Sonically, this Nelle Hooper-assisted single from Debut is something like a chanson in the Earth section of Epcot on Mars. Strings recorded at film studios in India do a ton of heavy lifting; every figure sounds like a different variation on swooning. At once intelligible and singular, "Venus" encapsulated Björk's particular pop genius so preciously. –Rich Juzwiak

Listen: Björk, "Venus as a Boy"

DGC / Rough Trade

Released right at the start of the 1990s, the Sundays’ second single had more than one leg stuck in the 1980s, its gentle jangle pop and bookish miserabilism inevitably recalling fellow Rough Trade signees the Smiths. At the same time, "Here's Where the Story Ends" has such a titanically strong pop melody—conveying a bittersweet tale of nostalgic longing that has withstood covers by artists as diverse as sugary house merchants Tin Tin Out and American Idol runner-up Crystal Bowersox—that it feels untethered to anything as prosaic as the calendar year. "Here's Where the Story Ends" is an irresistible ode to moping around in your bedroom, borne aloft and into the stars on David Gavurin's silk-slipper acoustic-guitar textures and Harriet Wheeler's crystalline delivery. It influenced the gentler side of Britpop and it will resonate for as long as young people feel sorry for themselves—which is to say, probably forever. –Ben Cardew

Listen: The Sundays, "Here's Where the Story Ends"

SuperEgo

Aimee Mann spent the ’90s sparring with a music industry that had desperately tried to control her. After leaving the ’80s synth rock group ’Til Tuesday, Mann went through a tumultuous run of contractual battles and label restructurings that left her both adrift and hardened. With "Save Me," she found a way out. The melancholy song was written for Mann's third solo LP—and first on her own label, SuperEgo—which shares DNA with the director Paul Thomas Anderson's Oscar-nominated 1999 film Magnolia. Anderson wrote his screenplay using Mann's cutting lyrics as dialogue, working together with the singer-songwriter to give flesh and blood to intricate stories about "the ranks of the freaks who suspect they could never love anyone," as she puts it in the song. Subtly informed by a long period of disappointment, "Save Me" is wry but surefooted, with its loping guitar melodies, shuddering accordion, and gentle percussion. The featherlight production and songwriting belie its inevitable punch: Here, Mann underscores the raw tenderness that comes with searching for help. –Eric Torres

Listen: Aimee Mann, "Save Me"

Wing

"Play this record as frequently as possible. Then, as it becomes easier for you, play the record once a day or as needed." The old-timey voiceover that introduced the Oakland trio's first big song set a high bar that this tune would be the cure for what ailed listeners, but that first drum hits like a full syringe of serotonin. With all the sweet harmonies and big beats that defined new jack swing, "Feels Good" stands out as a titan of the genre, a full-bodied five-minute mission to live up to its name, and a catalyst for the prolific career of artist-producer Raphael Saadiq. One of the thousands of songs to sample Lyn Collins’ 1972 James Brown-produced "Think (About It)," "Feels Good" drew heavily from older funk, soul, gospel, and jazz, while also embracing the hard-hitting sound of the era. It was part love song to a girl, part love song to music in general, and all party. –Evie Nagy

Listen: Tony! Toni! Toné!, "Feels Good"

Creation / Sire

"When You Sleep" is a firework of emotion gone awry, a love song that leaves you so helplessly and hazily entranced. On their shoegaze-pioneering album Loveless, My Bloody Valentine were intent on making their instruments sound just as destructive as these emotions, and "When You Sleep" is filled with indelible blown-out noise, shattered guitar feedback, and muddled confessions narrowly escaping the surface: "When I look at you/Oh, I don't know what's real," Shields sang, barely perceptible. Was this reality, or was it a dream? Either way, there was no exit. –Gio Santiago

Listen: My Bloody Valentine, "When You Sleep"

Chrysalis / EMI

"It was recorded as a joke," Gang Starr's DJ Premier once said of "Mass Appeal." "We just wanted to make fun of the radio on what it sounded like to get airplay." The infamous song is smooth like some chinchilla coat worn by a gangster's daughter—but nowhere near as soft. Guru's voice, scholarly and crystalline, is compact over Preemo's precise beat. Even though Gang Starr were non-violent, they weren't only for the backpackers, either. And while Guru wasn't a hustler rapper, he was still hardcore, his flow too confident for any posturing or ornamentation. They spoke to so many of rap's constituencies at once. Preemo might have created this song as a gag, but it stands firm as both criticism and corrective. –Jayson Buford

Listen: Gang Starr, "Mass Appeal"

Epic

Groove Theory only had one album and one hit, but they made it count. "Tell Me" was a simple, sensual admission of affection by singer-songwriter Amel Larrieux that captured all of the genuine nerves and excitement accompanying bubbling romance, set over a heartsick and woozy groove. "If you thought I’d sleep on this/Boy, you're wrong ’cause all I dream about is our first kiss," she sings, her voice both a sultry come-on and a raw confessional. All of this, combined with the unforgettable melody and producer Bryce Wilson's bulletproof bassline, made "Tell Me" a near-perfect representative of the best that R&B could be. –Evie Nagy

Listen: Groove Theory, "Tell Me"

Capitol

Cocteau Twins entered the ’90s with birth (Elizabeth Fraser and Robin Guthrie's daughter), death (Simon Raymonde's father), agony (Guthrie's substance abuse), and success (their highest charting U.S. single, "Carolyn's Fingers"). This complex concoction seems fit for a band that melded hope with heartbreak, embodying indescribable emotions through ethereal instrumentals and cryptic lyrics. "Cherry-Coloured Funk," the opening track to their 1990 tour de force Heaven or Las Vegas, drips with thick, sticky desire. Over lush guitar and churning bass, Fraser begins in an almost sinister low register, painting an abstract bucolic scene, then climbs to an anguished falsetto cry. As a feeling, "Cherry-Coloured Funk" is familiar yet ineffable, and thankfully expressed by a band who understood the inexpressible. –Arjun Srivatsa

Listen: Cocteau Twins, "Cherry-Coloured Funk"

Satellite / Logic

Movie directors aiming to create suspense or tension have been known to deploy what's called the Shepard tone, an arrangement that gives the illusion of a continuously rising siren sound. In 1997, UK garage producers were using a similar effect to signal the arrival of something much more thrilling: A big, bulbous bassline to put the wind up your Moschino shirt. In the hands of Double 99, that suspense comes from a wailing, rotating Tina Moore vocal chop that rides atop a trundle of plump kicks before eventually—it's a long build even by speed-garage standards—a delayed, distorted "brock wild!" summons a walloping bassline that's become instantly recognizable to ravers of all stripes over the subsequent decades. Just like that Shepard tone, it's still going. –Will Pritchard

Listen: Double 99, "Ripgroove"

Razor Sharp / Epic / Sony

Beholding the power of Wu-Tang at their peak was like stumbling onto the world's most esoteric track meet—cryptic smartasses bombing hammers and javelins all over the field, with points awarded according to the precepts of Supreme Mathematics. "Daytona 500" fulfills the title's promise of speed: Over a rubbery strut sampled from Bob James’ jazz workhorse "Nautilus," Raekwon's leadoff leg effortlessly piles up internal rhymes and mordant asides. Ghost follows with his particular blend of artisanal flexes ("In the Philippines, pick herbal beans") and invincibility ("I slapbox with Jesus, lick shots at Joseph"). They build a big enough lead for Cappa to break the tape, beer sloshing out of his cup. –Brad Shoup

Listen: Ghostface Killah, "Daytona 500" [ft. Raekwon, Cappadonna, and Force M.D.s]

RCA

In the comments section for a four-minute YouTube clip from 1993's Free Willy, hundreds have communed to honor a cinematic moment from childhood that gave them "chills." As Willy's fins cut through the water, the sound of Michael Jackson's reinterpolated "Human Nature" shimmers like the sun-jeweled waves, and the sound of SWV's voices gently rain down like drops of holy water. Chills. Sitting somewhere snug between the ecstatic and absolute serene, SWV's "Right Here (Human Nature Remix)" belongs as much in the church as it does the Free Willy soundtrack. With its gospel-infused harmonies, Teddy Riley's remix combines the classic romanticism and cool insouciance of the original with updated, widescreen hip-hop production (including a cameo from his protégé, Pharrell). –Emma Madden

Listen: SWV, "Right Here (Human Nature Remix)"

Reprise

In 1999, Wilco were set on blowing up their alt-country identity and stepping further into their truth as aesthetes. On Summerteeth, the band embraced the psychedelia of Beach Boys baroque pop, weaving in ever more textural experimentation. "Via Chicago" is the most stunning signal of what was to come on their 2001 opus, Yankee Hotel Foxtrot: the song deconstructs, as if slowly collapsing on the road back to their city and their people. "I’m coming home/Via Chicago," Jeff Tweedy sings, gently and wearied, broken yet whole, proof that place is only the first stop en route to the complicated comforts of home. –Jenn Pelly

Listen: Wilco, "Via Chicago"

East West

Yo-Yo made her recording debut in 1990, matching Ice Cube bar for bar on "It's a Man's World"—but her second solo single, in 1991, was stratospheric, an infectious declaration laying out Yo-Yo's plan for woman-domination in the entrenched male landscape of West Coast gangsta rap. Over Cube's lowrider-slow sample of Earth, Wind & Fire's "Devotion" and a refrain that cast a mournful pallor over its demands ("don't try to play me out"), the Compton-born Yo-Yo flowed majestically about her skills, intellect, style, values, and street bona fides, all while laying out a credo for herself and her crew, the Intelligent Black Woman's Coalition (IBWC). The blessing of Cube lent Yo-Yo some legitimacy in those sexist circles and helped her land a record deal by the time she was 18, but her flow spoke for itself, a protegee turned spiritual predecessor to current rappers as wide-ranging as Saweetie to City Girls to Omeretta the Great. –Julianne Escobedo Shepherd

Listen: Yo-Yo, "You Can't Play With My Yo-Yo" [ft. Ice Cube]

Virgin

Women. Ever heard of them? For much of the nineties the British cultural landscape had been suffused with the banality of blokiness, to the point where femininity felt like radical counter-programming. The Spice Girls were cartoonish splinters of British girlhood, each of them campishly endowed with femdom archetypes: Scary, Baby, Posh, Sporty, and… Ginger. "Wannabe," their debut single, was a boisterous, friendship-forward anthem centering the most hoydenish parts of their personalities. The five women delivered sass and brattiness with the giddy mania of a toy commercial—Friendship! Fun! Zig-ah-zig-ah! The track itself is indulgently weird, frantically jittering from one idea to the next without any thought or collecting breath. It sounds like pop music held at gunpoint, but this energy reinscribed a much-needed sense of humor and unseriousness into the genre. –Emma Madden

Listen: Spice Girls, "Wannabe"

Bulk / Mo' Wax

Kool Keith has had plenty of receptive collaborators both before and after his initial turn as the time-traveling alien OB/GYN Dr. Octagon, but none understood or complemented him as well as Dan the Automator. On 1996's Dr. Octagonecologyst, the producer keeps Keith from flying too far into the atmosphere with rocksteady boom-bap, while tickling the rapper's one-of-a-kind brain with wiggly synth drones, and samples from porn flicks and the cult ’90s comedy Cabin Boy. One clear highlight is "Blue Flowers," which features a horror-soundtrack-level flip of Bartók's Violin Concerto No. 2 alongside a jazzy backbeat. It's unsettling on its own, but Keith cranks up the disquiet with verses that are blood-soaked, heatsick, and wickedly funny. –Robert Ham

Listen: Dr. Octagon, "Blue Flowers"

LaFace / Arista

My Way was a path-changing album in Usher's discography, and on a record where every song had the potential to break out, "You Make Me Wanna…" had to be particularly spectacular to slightly edge out the others. A sublime mix of hip-hop cool and R&B seduction in the vein of Usher's idol, Bobby Brown, the song is sexy without being lascivious, playful without any childish inclinations, and just a little unbelievable. It's common to mourn the "death" of smooth, danceable and carefully produced R&B—an apparent bygone of a lost era—yet Usher's artistry has revealed itself to be committed to his roots, with a deep awareness of the foundational pillars lent to the genre by gospel and soul. As the years have passed, he's shifted and experimented, all the while pledging allegiance to the melodies that raised and introduced him. –Tarisai Ngangura

Listen: Usher, "You Make Me Wanna…"

Elektra

In which prototypical ’80s speed metal headbangers trade in thrash velocity and prog drama for a more straightforward and compact grunge-adjacent churn, in service of a spooky-ooky bedtime story named for a 19th Century continental European shuteye myth you can trace through ’50s girl-group dreamers the Chordettes, dirging ’70s soft-rockers America, a ’30s DC Comic-turned-’80s Neil Gaiman graphic novel, and maybe, just maybe, months after the Gulf War, Saddam Hussein. Add references to the turn-of-18th-Century Protestant children's prayer "Now I Lay Me Down to Sleep," the Southern folk lullaby "Hush Little Baby," and Peter Pan's (if not Michael Jackson's) Neverland, warn of "the beast under your bed, in your closet, in your head" (for the tween boy in the video, impending puberty maybe?), and you’ve got a sellout that goes bump in the night. Exit light, enter nye-yite, welcome to Metallica's nightmare. –Chuck Eddy

Listen: Metallica, "Enter Sandman"

Loud

"Ice Cream" sounds just as roughneck as the grimiest Wu bangers, so it's a little funny that Raekwon hated the song at first because he thought it was "too soft." RZA turns jazz guitarist Earl Klugh's plucky riff into a blood-curdling loop that cradles the Chef, Ghostface, and Cappadonna's confidence-oozing player raps. The three of them sound like guys fighting to get the attention of a beautiful woman who just passed by their block, verbally shoving each other out the way to shout the wildest compliments imaginable. Not all of their hollering has aged well—especially parts of Raekwon's verse—but it's still a quintessential New York rap love story: a little too upfront, yet romantic in its own crude way. –Brandon Callender

Listen: Raekwon, "Ice Cream" [ft. Method Man, Ghostface Killah, and Cappadonna]

Capitol Nashville

One of the best-selling artist of the ’90s, Garth Brooks was primarily influenced by Texas country acts like George Strait, and he wore a Stetson to prove it. "Friends in Low Places," the ultimate hat act single, starts off as a nearly a cappella story-song about storming an ex's high-falutin’ shindig, and Brooks attacks that chorus in a way that justifies every Elvis comparison. The song inevitably climaxes as a barroom sing-along that's musical and spiritual kin to Lone Star anthems like Tanya Tucker's "Texas (When I Die)." It's also Garth's pledge as a country singer—especially one hailed as the genre's conquering hero—to bring some low-class kicks to the high-class sales charts and record books. –Stephen Deusner

Listen: Garth Brooks, "Friends in Low Places"

XL / Maverick / Mute

Rave as metal—or oi!, maybe—with indie rock wah-wah borrowed from the Breeders, deep house bam-bam from Ten City, proto-techno "hey hey!" from Art of Noise, and a pyromania-horror concept from Stephen King. Keith Flint, him of the Bozo the Clown hair-tufts, slings Cockney rhyming slang about what a bloomin’ rebel he is— or, per his chants, what a trouble starter, punkin’ instigator, mind detonator, twisted animator he is. That last one was particularly apt since these blokes were nothing if not cartoons—but cartoons with the big beat, sillier and catchier and buzzier than just about anything else on the radio at the time. All told, a master class in how to sell electronic dance music as what looks and feels like a "rock band." –Chuck Eddy

Listen: The Prodigy, "Firestarter"

Rough Trade

Do you know just how low it feels to think the whole world is enjoying a party and you’re the only one not invited? Or to believe that most every possible comfort—the playfulness of a pet, the ecstasy of a holiday, the warmth of a smile, the silence of your space—is unavailable, denied for some reason you can't comprehend? That is the listless sadness at the core of "Fourth of July," a song about wanting to be loved by a crowd too busy to bother. Dean Wareham shuffles around New York, unimpressed by its Empire State Building's stature and uninterested in its Independence Day clamor. Naomi Yang and Damon Krukowski perfectly illustrate his anxious pacing, their circular rhythm moving like someone who wants to go anywhere but has nowhere willing to take him. What to do when the world shuts you out? Shut yourself in and take a glorious guitar solo that forever wanders, just like you. –Grayson Haver Currin

Listen: Galaxie 500, "Fourth of July"

Tommy Boy

"Superthug," the breakout hit from goofily intense rapper Noreaga (aka N.O.R.E.), not only launched a new era of Queens rap, pushing aside the cool and collected storm clouds of Nas and Mobb Deep with one fell swoop of its indelible "what-what-what-what-what-what-what" hook. It also heralded the arrival of producers Pharrell Williams and Chad Hugo, aka the Neptunes, onto the international stage. Their signature stuttering drums and sci-fi synths sounded unlike anything playing on Hot 97 at the time, foretelling the innovative path Williams and Hugo would chart for decades to come. –Claire Lobenfeld

Listen: Noreaga, "Superthug"

DreamWorks

In the long history of songs about other songs, "Waltz #2 (XO)" ranks as one of the best. Inside a smoky karaoke bar, a man and a woman—two people who may very well be stand-ins for Elliott Smith's mother, Bunny, and his stepfather, Charlie—select songs that thinly veil their marital strife. She blankly performs the humiliating "Cathy's Clown," he sings the pointed "You’re No Good." Smith uses karaoke night, or as he calls it, "the substitute scene," to give us this meta novella about pop music and heartbreak. He becomes an audience member inside his own composition, distant and helpless to do anything but silently show his love for his distraught mom, signed with a kiss and a hug. –Jeremy D. Larson

Listen: Elliott Smith, "Waltz #2 (XO)"

EastWest

Lord help the man at the business end of an "Oooooooooooo BOP." With its searing James Brown sample, stunning vocals, and biting parenthetical title, "My Lovin’" was En Vogue's 1992 entry into the proud tradition of soul anthems by pissed-off women who were absolutely done being used and disrespected. But the four-member girl group from Oakland added the all-important squad element, and this dirtbag trying to sweet talk his lady back after treating her like crap never stood a chance. What makes you think you can just walk back into her life, indeed. –Evie Nagy

Listen: En Vogue, "My Lovin’ (You’re Never Gonna Get It)"

Creation

Shoegaze is about capturing the shimmering melancholia at the edge of existence, that too-stoned sense of being unmoored in the world. "Alison," from one of the best shoegaze acts to ever do it, taps into that sinking feeling of lying in bed, wishing you could stay there forever but knowing you eventually have to face the universe. The song has a shaggy, nostalgic comfort, its warmth shining through like a lazy sunbeam on your face. But it's also tinged with unbearable loss, as the protagonist addresses a flawed person whose existence animates their being. "I’ll be here in the morning," Neil Halstead sings, even as he's the one who needs reassuring. –Cat Zhang

Listen: Slowdive, "Alison"

Bad Boy / Arista

You can practically feel the breeze of a whirring cash machine in your face. Produced by Deric "D-Dot" Angelettie of Bad Boy Records’ Hitmen production squad, this instrumental floats like a swarm of wasps, held aloft by a slowed and reversed sample of the opening guitar lick from R&B trio Love Unlimited's 1977 single "I Did It for Love." There's enough room in the pocket of this beat to fit a giraffe riding a 747—or a rap crew at the peak of their powers.

Nearly every line is now a certified classic, etched into NYC brownstone, from Puffy's immortal, Jadakiss-penned opening spray—"Now what y’all wanna do?!/Wanna be ballers, shot callers, brawlers?"—to Sheek Louch's quest for "colossal-sized Picassos" to Lil’ Kim throwing hexes and Angela Landsbury references at rivals real and imagined. (Legend has it the Lox's third member, Styles P, was cut from the track by a pre-fame Missy Elliott, who helped with the arrangement.) The production switches to a Jackson 5 flip for Biggie's anchor verse, suggesting a separate plane of existence: Upon its release months after the rapper's 1997 murder, this definitive version of "It's All About the Benjamins" doubled as a statement of defiance and a raucous respite from tragedy. –Ryan Dombal

Listen: Puff Daddy, "All About the Benjamins"

Arista

"The Sign" is the kind of uncomplicated, unserious pop song that's easy to love: there are those diet-reggae guitar licks, that pulsing drum-machine beat, and vague, chirpy lyrics that you can memorize almost instantly, even though you don't actually know what the song is about. (Technically, it chronicles a couple discovering a renewed sense of purpose in their relationship, but that's beside the point). When it was released in 1993 on the Swedish quartet's debut album, it exploded internationally; even member Ulf Ekberg's past in a skinhead gang didn't stop the band's ascent, though it definitely demanded some damage control. "The Sign" was a product of the Swedish pop machine, a system that produced a certain kind of flawlessly constructed, ultra-polished pop commodity. Exemplified by groups like ABBA in the ’70s, "The Sign" heralded its return two decades later, restoring a formula that would dominate the pop charts in the years to come. –Isabelia Herrera

Listen: Ace of Base, "The Sign"

VP / Slammin' Vinyl

Beenie Man understands the power of an eternal groove. The Playground riddim produced by veteran producer Jeremy Harding caught the Jamaican dancehall DJ's ear, and he reportedly showed up at Harding's studio with the song that would become "Who Am I" already in mind. "Who Am I" pulses like any good dancehall song, but at its heart is a man shook up about being left by his favorite lover, now forced to confront his own conniving ways with the help of love, shame, and some Luther Vandross interpolations. The track is foundational for modern dancehall and has been interpolated, sampled, and referenced countless times, but few follow-ups have captured the original's intoxicating mix of love and lust. –Dylan Green

Listen: Beenie Man, "Who Am I"

Creation

Britpop had plenty to answer for (see, especially, Menswe@r). But at its best it worked as a collective celebration of the humane things about the late 20th century: classic pop, social democracy, the fleeting empowerment of working-class culture. Released at the height of Oasis’ Augustan phase, "Don't Look Back in Anger" epitomized Britpop's historic sense in both form and context. Musically, away from the nonsense lyrics, it evoked the communitarian early ’70s, with an "Imagine" steal, Harrison-esque guitar licks, and ‘"All the Young Dudes" allusions. More broadly, as it attained Great Singalong status in the late ’90s, the eulogistic anthem came to embody a brief moment when exalting the better side of the past and looking forward to a brighter future seemed to work in harmony. In a decade when surface was depth, no song managed to mean so little and yet so much at the same time. –Alex Niven

Listen: Oasis, "Don't Look Back in Anger"

Tommy Boy / Warner Bros.

Three quarters of the way into "Swahililand," a 10-minute jazz odyssey by the great pianist Ahmad Jamal, you can hear J Dilla's ears perk up in his record-filled Detroit basement. He recognized a perfect sample, an urgent and dramatic chord progression that became the looping heart of De La Soul's "Stakes Is High." The trio's message on the song was bold—they’d grown sick of the fake shit, the gaudy capitalist-fantasy videos, and the rappers play-acting as drug lords without saying anything substantial about the crack epidemic. "Stakes Is High" was a line in the sand backed by one of Dilla's most iconic beats—a template for a different way ahead from the stuff getting airtime on MTV. –Evan Minsker

Listen: De La Soul, "Stakes Is High"

Underground Resistance

"Jupiter Jazz" sounds like one of those airbrushed sci-fi book covers of the late ’70s and early ’80s looks: galaxian synth melodies and whirring, bubbling space noises floating over beats that echo the rhythmic complexity of jazz as played by drum machines. Underground Resistance's "Mad" Mike Banks may be better known for uncompromising techno and militant aesthetics, but this record is fun and hopeful, as playful rave stabs and dreamy Motor City pads give way to an elegant mission statement about techno as "hi-tech jazz." Back in 1992, UR's live band didn't physically exist yet, but you can see the idea taking shape over EPs like Nation 2 Nation, World 2 World (the EP that contains this track), and 1993's Galaxy 2 Galaxy. Like all good space explorations, Banks’ endeavor has taken time and patience, but the Galaxy 2 Galaxy live ensemble fulfills the promise of "Jupiter Jazz," bringing together several generations of Detroit Afrofuturists—from sax players to synth wizards—to play timeless, tireless grooves. –Vivian Host

Listen: Galaxy 2 Galaxy, "Jupiter Jazz"

Virgin

During the recording of Smashing Pumpkins’ Siamese Dream, frontman Billy Corgan demanded absolute perfection from those around him. In liner notes for the album's reissue, he referenced recording "thousands" of drum takes to tape that had been spliced so much it was disintegrating. It was this relentless drive, in part, that made him stand out from his peers, who were wading through swampy distortion with snarling disaffection. For Corgan, caring was cool—and "Mayonaise," a lonely meditation on the beauty of owning your shortcomings, was something of a mission statement. Amid a record of songs about abuse, suicide, and bearing the weight of the world, it's a lushly arranged moment of peace, reframing Corgan's relentless perfectionism as a kind of perseverance. –Colin Joyce

Listen: Smashing Pumpkins, "Mayonaise"

Loud / RCA

Big Pun's trademark ode to the players and pimps continues to ring out in the streets of the South Bronx. Pun was the precursor to the Bad Bunnys and Cardi Bs of the current scene, a hip-hop trailblazer for Latinos all over the map. He created a sound and dialect that was unmatched at the time, rapping in Spanish one moment and then in English the next, dense sheets of compound rhymes pouring out of him, the wordplay at once rapidfire and unhurried. "Still Not a Player" remains a staple of Puerto Rican Day parades; it's what every papi hears before heading over to the block to hang. Especially in Pun's native borough, it still sounds like home. –Jayson Buford

Listen: Big Pun, "Still Not a Player"

Warner Bros.

"Losing My Religion" is the ultimate back-door hit—so unorthodox in its composition yet so representative of its creators’ strengths. Grown entirely from a single riff on the mandolin, an instrument that was completely new to guitarist Peter Buck at the time, the song captures R.E.M. at their most synergistic, resolute, and vulnerable. Michael Stipe sings like he's afraid of his own shadow, and he's stalked and swarmed by Buck, bassist Mike Mills, and drummer Bill Berry as he winces his way through a string of wounded confessions that are both specific-seeming and interpretable, whether through a lens of religion (it wasn't intended that way), unrequited love (Stipe has cited "Every Breath You Take" as a major inspiration), or the view from the corner or the spotlight. –Steven Arroyo

Listen: R.E.M., "Losing My Religion"

Virgin

Kelis has said that "Caught Out There," her debut single, recorded when she was just 20 years old, "set the tone for my entire life." It was an early and formative Neptunes production, with bouncy keyboards and a pew-pew sound effect that can only be compared to laser guns, but their collaboration eventually soured. It was ahead of its time, which meant the timing was off, which makes it a "cult favorite"—a euphemism for "not as popular as it should have been" and a way of signaling taste and discernment that would, rather unfairly, dog Kelis for much of her career. But it was also an anthem for women's aggrievement, the song that made her, with its ferocious, shouting hook, "the first girl to scream on a track," as she would later remind us. For all she's been through over the years, it makes sense that Kelis came out kicking. –Emma Carmichael

Listen: Kelis, "Caught Out There"

Matador

Nothing the local coffee shop cues on chilly days can compare to "Autumn Sweater," a downy song about our sentimental attachment to mementos, but more acutely, about wanting to disappear with the person you love. Is the charm in lead singer Ira Kaplan's shy, sweet delivery, murmuring his proposal as if his hands are tucked nervously into his pockets, or in the unassuming but lively instrumentation—the rattle of the shakers, the bright tones of the organ, the syncopated groove of the congos? Few songs stake the same claim on a season, the nervousness and possibility stirred up when the air picks up a draft. –Cat Zhang

Listen: Yo La Tengo, "Autumn Sweater"

Def Jam / Columbia

Public Enemy's 1990 single "Welcome to the Terrordome" has complicated roots. On the one hand, it's a musical Molotov lobbed at the powers of white supremacy much like "Fight the Power," which soundtracked Spike Lee's Do the Right Thing the year before. But it's also a response to the controversy stirred up by Professor Griff, Public Enemy's onetime Minister of Information, whose inflammatory anti-Semitic comments brought down a shitstorm of opprobrium on the group, eventually resulting in Griff's dismissal. Chuck D references the flap in a few lines, and not, admittedly, to his benefit ("Crucifixion ain't no fiction/So-called chosen frozen"; "Told a Rab to get off the rag"). But the force of his defiance, as he details the indignities visited upon Black Americans, paired with the claustrophobic apocalyptic feel of Hank Shocklee's production, is nonetheless thrilling, in a real pit-in-your-stomach way. –Philip Sherburne

Listen: Public Enemy, "Welcome to the Terrordome"

Interscope

Ska-pop band No Doubt's 1995 hit "Just a Girl" was a sassy indictment of institutional sexism subtle enough to skank its way onto the charts. Atop a squiggly riff, Gwen Stefani outlines an experience of girlhood inhibited by the patriarchy: "I’m just a girl, all pretty and petite/So don't let me have any rights," she sneers. "Just a Girl"'s feminism is cleverly transgressive: beyond her sarcastic delivery, Stefani's vocals jump from babydoll soft to full-chested belting, playing with the stereotypes of the fragile waif and the angry woman. These identities combine in the song's final moments. "Oh, I’ve had it up to here," Stefani belts, her frustration unignorable. But then she lets the final word wilt like a flower. Is she surrendering or wantonly using the infantilization she just spent a whole song decrying as a mechanism of power? Girlhood has always been more complex than it seems. –Quinn Moreland

Listen: No Doubt, "Just a Girl"

Fiction / Elektra

"Friday I’m in Love" is a happy song. Right? The ebullient jangle of the guitars; that melody, so easy and intuitive and right that Robert Smith was convinced for a while that he’d stolen it from somewhere else; and the titular line, yelped with the enthusiasm of a puppy waiting for a treat. Who could be sad on Friday? Not even Smith. But it only comes once a week, and you already know what the other days are like. Monday: Black. Tuesday, Wednesday: Heart attack. And on it goes until Friday lights us up again, however briefly. The Cure's final hit is an ode to the ecstasy that finds us only occasionally, taking its unsteady foothold before drudgery washes it away again. Still, those guitars and that melody make clear that it really is a happy song. Smith and the band recognize that joy's rarity makes it all the more precious, and that finding it for even one day per week is a cause for celebration. Here's to feeling good roughly 14 percent of the time. –Andy Cush

Listen: The Cure, "Friday I’m in Love"

Tommy Boy / Warner Bros.

De La Soul Is Dead found the group reckoning with their Day-Glo debut, 3 Feet High and Rising, spiking their rap hippie rep with darker humor and edgier storytelling. But they didn't spend the entire album clearing the air. "A Roller Skating Jam Named ‘Saturdays’" radiates relief, with De La roping in fellow Native Tongues members Q-Tip and Vinia Mojica for a breezy ode to the best day of the week. The verses, the chorus, and even the record scratches glide over Prince Paul's silky beat, which blends disco, funk, and the Grease theme into a springy delight. Like a Saturday, it is contained but boundless, a Cinderella slipper for the whole squad. –Stephen Kearse

Listen: De La Soul, "A Rollerskating Jam Named ‘Saturdays’"

Hut / Virgin

Until the matter was settled in 2019, the Verve's "Bitter Sweet Symphony" was less a pop song than a rollicking, anthemic full-employment act for intellectual property lawyers. The fight centered around the hook's sample of four bars of Andrew Loog Oldham's orchestral version of the Rolling Stones’ "The Last Time," which was itself borrowing from an old gospel song. The Verve was cut out of a fortune's worth of royalties, the Stones got fractionally richer, and the whole mess overshadowed what was maybe the best song of the Britpop moment. Just luxuriate in the Spectory thickness of the production—"a prairie-music kind of sound," in the evocative phrase of the Verve's Richard Ashcroft, who cited the Temptations and Ennio Morricone as models. It is an epic, the best sort of grandiose, the music soaring where the words want to mope. Maybe all the legal shitfighting wound up saying the thing the lyrics couldn't quite articulate. What better summation of the present era, after all, than the meta-story of "Bitter Sweet Symphony"—some asset-holding boomers got wealthier without leaving the couch and everyone else was stuck holding the bag. –Tommy Craggs

Listen: The Verve, "Bitter Sweet Symphony"

Jive

"Why you let these killas live and take my homeboy son away?" Pimp C asks on UGK's most significant album, 1996's Ridin’ Dirty. The moment is a call to God for answers, none of which the man born Chad Butler would ever get. UGK found the darkest piece of the blues over a flip of The Isley Brothers’ "Ain't I Been Good to You" while charting through nihilism, the loss of friendship, and the finality of death. "One Day" is a solemn funeral procession, where Bun B, Pimp C, and featured rapper Mr. 3-2 understand that being Black can mean your final days come over a "funky-ass dice game," on the uneven scales of the criminal justice system, or even worse—by an unimaginable act of God. –Brandon Caldwell

Listen: UGK, "One Day"

East West

Appearing on a genre-fluid album laced with doo-wop-like jams like "My Lovin’ (You’re Never Gonna Get It)" and sensual classics like "Giving Him Something He Can Feel," En Vogue's "Free Your Mind" took us to rock as thrashing metal guitar riffs layered with keyboards, the group's signature harmony, and a message of gender and racial unity. "It doesn't mean that I’m a prostitute, no, no," these curvaceous Black femmes in thigh-high boots wanted us to know—a radical message at a time when feminism was all but declared dead and a war on women was underway. Slut-shaming and moral judgment were the norm, not the exception, and "Free Your Mind" was an anthem to STFU and leave people be. –Samhita Mukhopadhyay

Listen: En Vogue, "Free Your Mind"

Merge

The only thing worse than a miserable low-paying job is having to compensate for the absolute dud working the same shift, and Superchunk bottled both dimensions of that rage perfectly in their joyously explosive breakout single. The layabout muse of "Slack Motherfucker" was a guy Mac McCaughan worked with at Kinko's, but the specific dude matters not. He is an archetype that exists in every bad job—the person taking too many smoke breaks, who leans when he could clean, whose lack of work makes it so you have to stay late. When the band shouts the chorus and the final repeated strains of "you motherfucker," that's a universal release that anybody can scream along to. –Evan Minsker

Listen: Superchunk, "Slack Motherfucker"

RAM

If you were at a drum’n’bass rave at any point in the ’90s, chances are you know the feeling of being in "a long, dark tunnel," a sensation forever trademarked by the sample in Andy C and Ant Miles’ iconic 1993 anthem "Valley of the Shadows." The track contains little more than arpeggiated bells, a shuffling "Think" break, eerie pads, and a "31 seconds" soundbite from the Apollo 11 moon landing—mostly sounds from a free sample CD that came with a 1993 issue of Future Music magazine—yet it sums up the darkcore aesthetic of early jungle with chilling simplicity (and some seriously deadly sine-wave bass). Nearly 30 years on, Andy C is drum’n’bass’ top DJ, and RAM has over 440 releases to its name. In a genre that's come to be associated with daredevil drops and over-the-top production trickery, you can still get a mighty rewind off this stone-cold classic. –Vivian Host

Listen: Origin Unknown, "Valley of the Shadows"

RED / Relativity / Hypnotize Minds

Three 6 Mafia's first major-label contract required them to put "Tear Da Club Up" on their next record. In theory, not a huge ask—Chapter 2: World Domination ended up exhuming several hits from the Memphis crew's previous albums, where Juicy J and DJ Paul continually scraped layers of lo-fi graveyard grime off their horrorcore production style. But they were tired of that particular song. So the ’97 version converts the original's ambient dread into imminent dread, from the soap-opera piano ostinato to the four-note rising synth figure that chases each verse like Hell's breaking-news theme. Recent addition Gangsta Boo pops up halfway through to bigfoot the track; it's no wonder hers is the verse featured in the canny, nu-rock TV ad. Whether or not the song truly was "banned in 17 states," as that commercial claims, crunk grew from its wreckage. –Brad Shoup

Listen: Three 6 Mafia, "Tear Da Club Up"

Deceptive / Geffen

Swiping the electronic bop that fuels post-punk icons Wire's "Three Girl Rhumba"—an homage that eventually resulted in a lawsuit that was settled out of court—Elastica crafted one of the marvels of the Britpop era: art-rock reconfigured as a carnal rallying cry. All leftward hooks and innuendo, "Connection" never hits its target squarely—frontwoman Justine Frischmann alludes to its oblique construction by ending her chorus by admitting that "somehow the vital connection is made"—but the single sounds simple, even primal, as Elastica bashes their dive-bomb riff with enthusiasm. As soon as the song takes shape, when the suggestions start seeming like overt flirtations, Elastica pulls the plug: The "Connection" is fleeting, no matter how indelible it may be. –Stephen Thomas Erlewine

Listen: Elastica, "Connection"

Aftermath / Interscope

As with Beck's "Loser," you would have been forgiven at the time for taking Marshall Mathers' chicka-chicka-chart debut for a novelty-joke one-shot—nothing indicated a major career on the way. Right off, Slim Shady's gleefully introduced as a class clown and horrible role model ("Hi kids, do you like violence?"— "Primus" in the edited version—"Wanna see me stick Nine Inch Nails through each one of my eyelids?"). But he constantly sets up escape hatches, serving as peanut gallery ("Stop the tape! This kid needs to be locked away!"), and switching out of apparent autobiography only to catalog every satirical way he’ll wreak havoc on English teachers, autograph hounds, his own body (two fake suicides!), and his own Mom. "God sent me to piss the world off"—everybody has a purpose, right? –Chuck Eddy

Listen: Eminem, "My Name Is..."

Reprise

"I’m still in love with you," Neil Young sings during the chorus of his 1992 standard "Harvest Moon." You could spend a lifetime in that "still." The Canadian songwriter was in his mid-40s when he wrote it, and he seemed to use every minute of his time here to fuel its sense of romance and devotion. Backed by an autumnal lineup featuring Linda Ronstadt on vocal harmonies, Ben Keith on pedal steel, and Tim Drummond sweeping a broom for percussion, Young lets his guitar summon a vast distance—detuning the lowest string and letting it reverberate through the central riff, fingerpicking the harmonics high up the fretboard during the verses. The sound itself seems to conjure eternity, and the words do, too. Three decades into his career, Young had written plenty of songs about searching for a companion, about the heart-skipping joy of finding love and the ditched-out misery of losing it. Here was his simple, soulful prayer to making it last. –Sam Sodomsky

Listen: Neil Young, "Harvest Moon"

Virgin

Ephemeral, transcendent, sensual, groovy—"That's the Way Love Goes" is less a song than it is a vibe. From the first bouncy downbeat, your back relaxes, your head nods, and you let out a sigh: That is the way love goes. How can one feel so horny yet so chill at the same time? With Jackson's whispering vocals over Jimmy Jam and Terry Lewis’ delicate, soulful beat, it is one of the greatest songs ever released about the overwhelming yet meditative pangs of lust, hypnotic, like desire itself. "That's the Way Love Goes" was a mega-hit—the longest-running No. 1 single of any Jackson family artist—and the song, like the janet. album it appeared on, exposed us to a new Jackson: still soft-spoken but confident in her sexuality, her body, and her desire. –Samhita Mukhopadhyay

Listen: Janet Jackson, "That's the Way Love Goes"

Bad Boy / Arista

The sirening opening sample clears the streets and the bass shakes the pavement: Even if it weren't the last single to be released in Biggie's lifetime, "Hypnotize" would still be an eternal Brooklyn anthem. He's just that smooth, strutting effortlessly across a Puff Daddy beat that flips a chunky, convivial Herb Alpert bassline into a low-riding crawl. His writing plays off the subtlest nuances of his voice, flashing details as causally as checking his watch: colorful Coogi sweaters, freaky sex in the Lexus, a not-at-all-unconvincing threat to shoot you that turns into a preposterous one to kidnap the DA's daughter while he's at it. Yeah, all that—and one of the most iconic vocal hooks in hip-hop. –Anna Gaca

Listen: The Notorious B.I.G., "Hypnotize"

A&M

Women in ’90s rock were marketed by a male-dominated industry as angry, damaged, confessional, or exceedingly quirky. Sheryl Crow fit into the alternative mega-tent of mid-’90s pop, but not really any of these little boxes. The carefree cover of her jazz- and roots-inflected debut, 1993's Tuesday Night Music Club, could double as a Levi's ad, and its biggest hit, "All I Wanna Do," exalts the power of a good beer buzz in the morning. When Crow returned with her self-titled sophomore album in 1996, she was mired in expectations and ideas about her success and sound; she appears on the sepia-toned cover throwing stink eye from behind strands of hair, an attitude matched by the album's electrified pop-rock. Spiked with chugging guitars, lead single "If It Makes You Happy" works on several levels: as a rejoinder to cross-armed skeptics, an ironic portrait of a Gen-X boheme lifestyle (I like to imagine she's addressing Troy from Reality Bites), and a question Crow is asking about her own strange life. She references having a miserable time at Woodstock ’94, getting stoned, and making French toast from moldy bread, and her voice on the chorus soars and scrapes in equal measure. For a moment in time, Sheryl Crow was not the kind of girl you take home—and it was glorious. –Jill Mapes

Listen: Sheryl Crow, "If It Makes You Happy"

Kill Rock Stars

"Say Yes" arrives last on Either/Or—standing in the doorway, hesitating, with its shoes on. Elliott Smith actually clears his throat at the outset: Can he come in? Will you hear him out? At this point in Smith's career, before Good Will Hunting and the Oscars, before the transition to a larger label, listeners came to him for songs of abjection, making the sunny optimism of "Say Yes" seem like a hard sell. It's a straight-ahead love song, one that dares to hope. Listen closely and you’ll hear just how fragile that hope is: Smith whispers most of the song. He wavers. His fingers pluck out a simple question on the acoustic. He’ll accept no; he’ll leave if he's not wanted. But if there's a chance, even the slightest, of yes, he’d like to stay long enough to hear it. –Peyton Thomas

Listen: Elliott Smith, "Say Yes"

R & S

New York producer Joey Beltram's 1990 single "Energy Flash" was so brilliantly dumb, there were only two ways it could go: change the world or fall flat on its snarling face. There's almost nothing to it—pummeling kick drum, impudent sub-bass, vocal sample, and the occasional electronic flourish—but even that seems superfluous when held up against the viscerally compelling, technologically evil riff that runs through the song, a relentless and yet kind of funky half-note sledgehammer that resembles Black Sabbath's "Paranoid" recreated by murderous robots. "Energy Flash" is well named: The effect is like a high-voltage shot to the neurons that lit up dance floors all over the world; its irresistibly dark momentum shaped the sounds of hardcore, jungle, and techno as the utopian spirit of rave dissolved into a world of bad drugs and police busts. –Ben Cardew

Listen: Beltram, "Energy Flash"

Lench Mob / Priority

Ever since Chuck D analogized rap music as television news for Black America, critics, scholars, and fans have referenced how it reflects the everyday injustice and inequality in these communities in a way that's often missing from mainstream media. But the Black experience is about more than just oppression—something Ice Cube eloquently captured with this joyful single from his 1992 album The Predator. Written at the peak of his solo career, Cube's good day centers not on the trappings of wealth but on everyday events in his neighborhood; breakfast with his momma, the pickup game in the park, shooting dice with the homies. He experiences the kind of fortuitous luck afforded only to the most blessed: he cleans up at craps, his favorite basketball team beats a rival, and he connects with a girl he's long pined for. But beneath the happiness of a day when everything seems to go right is a latent anxiety over how easily things could go another way. He may have evaded the carjackers, the cops and the specter of death, but he knows they always lurk just around the corner. –Matthew Ismael Ruiz

Listen: Ice Cube, "It Was a Good Day"

DGC

The melody to "All Apologies" is so simple it seems as though someone, somewhere, must always have been singing it. Appropriately, it followed Kurt Cobain around for years in different forms: His undated acoustic home demo, thought to have originated around 1990, was pleading and sincere, while the version the band tracked in 1991 but left off Nevermind was sardonic and sloppy. As the song lurched towards its final self, sharpening early lyrics and gaining a cello, it began to radiate a vast, frightening exhaustion. Feelings this big trail us for years before revealing their awesome face, and by the time Cobain was onstage performing it for MTV Unplugged: Live in New York, it had the clarity and finality of epiphany. It's always been interpreted as a suicide note, but really it's just a master statement. The song held everything: tenderness and bitterness, anger and acceptance, love and hatred, resignation and revelation. What else could he say? –Jayson Greene

Listen: Nirvana, "All Apologies"

Jive

The in-the-booth, stream-of-consciousness rap song intro is a trope as old as hip-hop itself; mostly, these are space fillers that add little. But such is the magnetism of "93 ’Til Infinity" that when Tajai Massey says, "Right now, we just maxing in the studio," all of a sudden you’re right there with him, blunt smoke tickling your nostrils. For a hair under five minutes of breezy, rolling boom-bap, a single sax note glides in and out, pads drift and cut, and the drums—bop your head—don't ever stop. Tajai and crew toss bars and ad libs back and forth, all in sync, swigging from the same 40 in a freewheeling, effortless jam. By the time the final, closing roll call of who's chilling sails in, you half expect to hear your own name called out. –Will Pritchard

Listen: Souls of Mischief, "93 'Til Infinity"

U.N.I.T.Y

New York in 1990 was a vibrant place. Hip-hop and house music were changing by the month, and ruling the clubs in the process. It was also a scary one—the city's murder rate reached its peak that year with 2,245 killings, a huge increase over 1989. Joseph Longo was perfectly situated to capture that vibe in a bottle. A clerk at the 12-inch storehouse Vinylmania in Manhattan, he became a producer in the late ’80s and by 1990 was producing classics in both rap—Boogie Down Productions’ "Love's Gonna Get’cha (Material Love)"—and house, under aliases like Earth People and Pal Joey. As Soho, his "Hot Music" reconfigured airy Wynton Marsalis snippets over an all-business kick-drum pattern just off kilter enough to carry more than a hint of menace. "Playing ‘Hot Music’ usually caused chaos," Longo recalled in 2013. Decades on, it still does. –Michaelangelo Matos

Listen: Soho, "Hot Music"

LaFace

"Elevators (Me & You)," the lead single from ATLiens, was the moment when OutKast became bona fide stars. The beat is unmistakably cool, built around smooth bass, hi-hat drums, and an echoing wood block; there's just enough there to make the instrumental distinct, but also keep it uniquely mimnal. André 3000 and Big Boi match the understated poise in their verses, every word rolling off their tongues impeccably while telling the world how they patiently planned their ascent, all skill, no luck and no haste. It's the ultimate come-up song, a track that recounts André and Big Boi's rise from "Player's Ball" to ballers. –Matthew Strauss

Listen: OutKast, "Elevators (Me & You)"

Drag City / Matador

Was Pavement for real, really? The debate over how much frontman Stephen Malkmus gave a damn dangled perpetually over the Stockton, California band for its entire existence. Beavis and Butt-Head implored them to "try harder"; Robert Christgau saw through their hunched postures and declared them "well-schooled"; Pavement's original drummer, local hippie Gary Young, split the difference when he remarked, "This Malkmus idiot is a complete songwriting genius."

"Summer Babe (Winter Version)" sketches Malkmus’ balancing act between the court jester and the savant. It takes a foolish confidence to start your debut single with "Ice baby" only two years removed from Vanilla Ice's billboard-topping single, but the chainsaw revving of distorted guitars tips their hand—they were indeed "schooled" among the no-wave heavyweights of the late ’80s, and they had the hard-fought melodies to show for it. "Summer Babe" careens between self-seriousness and complete nonsense; when Malkmus sings, with an exasperated laugh, "Drop off," in the final stanza that could be called a verse, it's as if he's laughing at himself, sheepishly questioning whether to commit fully to the rock star act. But the beautiful thing about Pavement was that in the end, they always committed. –Arielle Gordon

Listen: Pavement, "Summer Babe"

Bad Boy

The first single released by Sean "Puff Daddy" Combs’ influential Bad Boy Records, Craig Mack's "Flava in Ya Ear" signaled a paradigm shift for New York rap via Mack's off-kilter flow and producer Easy Mo Bee's elasticky head-knock production. With the remix, featuring vets LL Cool J and Busta Rhymes, plus Bad Boy up-and-comer the Notorious B.I.G., Puffy cemented himself as a true forward-thinker. Mack and Biggie—pre-"Juicy"—are all laid-back bravado, a perfect foil for an unhinged Busta. But even amidst this posse cut's stacked lineup, Biggie's star power shone through. Nearly thirty years later, "Don't be mad, UPS is hiring" still stings. –Claire Lobenfeld

Listen: Craig Mack, "Flava in Ya Ear (Remix)" [ft. The Notorious B.I.G., LL Cool J, Rampage, and Busta Rhymes]

Sire / Warner Bros.

"Constant Craving" signified the Canadian crooner k.d. lang's official shift away from her alt-country roots toward a blend of klezmer and adult contemporary, a move which afforded its own set of risks and rewards. "I knew it was a hit, and I was mad at it for that," lang succinctly said of the song in 2018. It's easy enough to understand—lang's knotty songwriting, yearning mezzo-soprano, and that slyly sexy chorus are instantly undeniable, which led to new audiences and celebrity once it came out alongside an eerily beautiful video riffing on Waiting for Godot. But the song struck a separate nerve in 1992. What was usually made subtext in pop songs—that specifically queer longing that settles in the forefront of your attention for someone you aren't supposed to want, an emotion that may not be reciprocated but achingly lives on—was suddenly brought to the surface, sung by a woman who wore all the unmistakable markers of butch iconography, from the spiky gelled bouffant to the sharply tailored suits. lang came out as a lesbian in an issue of The Advocate the same year "Constant Craving" was released, leaving behind a large chunk of her country fan base in the process. But it was a choice that reaffirmed her status as an icon, once the song infiltrated the Hot 100 and assumed a life of its own in the cultural zeitgeist, tilting expectations for lang and all the queer singer-songwriters who have come since. –Eric Torres

Listen: k.d. lang, "Constant Craving"

MCA

"You Got Me" is a short story and a love song, a duet for three voices and a collective arrival, a ballad that enters with classical guitar arpeggios and exits with a drum‘n’bass break. It's also the lead single from Things Fall Apart, the Roots’ fourth studio album, recorded with the hopes of helping them finally break big. The devil's bargain? Switching out Jill Scott, who co-wrote the song, for Erykah Badu, the neo-soul queen of the moment. (The band made up with Scott later by taking her on tour.) Meanwhile, the song—a lovers’ back-and-forth, with Black Thought as the male lead and the female character split between an Eve verse and Badu's gentle, reassuring vocals—stuck, and helped propel the Roots to the mainstream. Despite the melancholic tone, the song is comforting, committing to the kind of care that keeps a relationship going strong despite the turbulence—as true for the track's collaborators as for its fictional protagonists. –NM Mashurov

Listen: The Roots, "You Got Me" [ft. Erykah Badu and Eve]

DGC

The ’90s arrived right on time for Sonic Youth, whose transition from heroes of New York art-punk to bona fide rock stars came six months into the dawning decade with the release of Goo, their major label debut. In style and subject matter, "Tunic (Song for Karen)" embodies their dual citizenship in the mainstream and the underground. For most of the song's six-minute runtime, it sounds like Sonic Youth as their cult of fans had come to know them thus far: The guitars are dense and dissonant, the groove is propulsive and unrelenting, the vocals follow a dreamy spoken cadence that has more in common with experimental theater than rock’n’roll. But when they downshift into the chorus, a half-time riff that swaggers in tandem with Kim Gordon's menacing refrain—"You aren't never going anywhere"—you can practically see the Lollapalooza crowd forming in front of them. The lyrics memorialize and pay homage to soft-rock megastar Karen Carpenter, who died of complications from anorexia—perhaps an unlikely subject for a group whose professed tastes ran toward the avant-garde. But Gordon shows real empathy for Carpenter, inhabiting her wounded psyche and celebrating her resilience in the face of public scrutiny. It's a fitting encapsulation of early-’90s Sonic Youth: unabashed about chasing fame, but clear-eyed about its dark side. –Andy Cush

Listen: Sonic Youth, "Tunic (Song for Karen)"

Ruffhouse

When Lauryn Hill first sang the hook on "Ready or Not," she had already decided to leave the Fugees. With tears in her eyes, she laid down a demo for the group to use; a few months later, when she’d rejoined them, she spent five hours trying to re-do the vocals, but no version came close to the rawness of that first recording, the one that gives the song its potent sense of foreboding and focus. Hill sings every word of the Delfonics interpolation with precision and anguish as she, Wyclef Jean, and Pras take turns flexing in the face of their rivals. The song is a kiss-off to other rappers, but her verse and performance also serves as a love letter to her bandmates. It's a poignant moment of cohesion from a group whose time together was steeped in turmoil. –Vrinda Jagota

Listen: Fugees, "Ready or Not"

Purpose Maker

A figure of Jeff Mills’ stature doesn't necessarily need a signature tune. But "The Bells" is exactly that: a fulcrum of his DJ sets to this day, and a cornerstone of Detroit techno in general. Unusually, for a tune with such an instant level of recognition, there's no obvious audience appeasement going on here—no crowd-pleasing sample, no big chorus. Instead, the effectiveness of "The Bells" seems to spring straight from its sleek simplicity. Just a springy 4/4 kick and snare, a pinging riff that dances around the offbeat, and a four-note chime set in a teasing refrain, all arranged to give the sense of a tumble down an infinite wormhole. Mills was playing "The Bells" out as early as 1994, so by the time it finally appeared on his Kat Moda EP in 1997, it already felt like a classic. –Louis Pattison

Listen: Jeff Mills, "The Bells"

Reprise

The members of Green Day grew up on the first wave of punk, and rethreaded the genre's pop fringes through the slacker vibe that would come to define the ’90s. "Basket Case" was a fizzy and petulant self-doubt anthem featuring sex and immortal existential questions like "Am I just paranoid, or am I just stoned?" (The answer was both.) Below its flippant veneer, the track is a sly reflection of ailing mental health: It was written when a 22-year-old Armstrong was struggling with severe anxiety, later diagnosed as a panic disorder. Lines like "Sometimes my mind plays tricks on me" and "I think I’m cracking up" sound blasé and unidentifiably snotty, but they reveal a young man desperately trying to make sense of his own thoughts. "Basket Case" does much more than whine, demonstrating an internalized self-fear finally breaking through to the surface, transferring punk energy to millions of young people coming of age and feeling just like Armstrong did. –Jane Bua

Listen: Green Day, "Basket Case"

Fondle 'Em

MF DOOM claims he "came to destroy rap" at the beginning of his 1999 debut Operation: Doomsday, but "Rhymes Like Dimes" proved his love of craft was equal to his love for chaos. He spends over four minutes juggling his disdain for the industry with his innate ability to spit truth, not just rocking a mic but giving people "something to remember like the Alamo." DOOM's malevolent and wry words clash with the self-produced beat, a loop of Quincy Jones’ "One Hundred Ways" that plinks and bounces with warm colorful synths. "Rhymes Like Dimes" is both a love letter to and a formal complaint about rap music that also introduced one of the largest personalities in the genre's history. Who else but a supervillain could manage all that? –Dylan Green

Listen: MF DOOM, "Rhymes Like Dimes"

Mercury Nashville

Shania Twain's opening credo—"Let's go, girls!"—isn't so much a call to arms as a champagne pop, an effervescent invitation to celebrate. Arriving at a time when riot grrrl's space-claiming had shifted into the capitalistic sheen of girl power, Twain's twangy pop equated feminism with being unapologetically herself, short skirts and all. Frenetic fiddles over the chorus marked the fading traces of her country music origins, as she deliberately pursued a more global pop audience without any of the hand-wringing that so often precedes that kind of leap. Twain's ambition, and the swaggering confidence fueling it, found millions of giddy listeners who just wanted to have a little fun right alongside her. –Amanda Wicks

Listen: Shania Twain, "Man! I Feel Like a Woman!"

Interscope / Jive

One of the greatest tricks 2Pac ever pulled was cultivating a tough-guy persona based on sensitivity. For all his party tracks and songs steeped in misogyny, he wasn't too cool to show emotion or delve into current events with a comforting sense of empathy. Even by those standards, "Keep Ya Head Up" is an ode to Black women and abortion rights that stands out as a gem in his discography. Producer DJ Daryl's funky sample of Zapp's "Be Alright" is the perfect cushion for reassurances of Black empowerment ("Some say the Blacker the berry, the sweeter the juice/I say the darker the skin, then the deeper the roots") and a full-throated defense of women from rapists and deadbeat fathers in a music world that rarely focused on them. All this clashes with the fact that barely a year after its release in October 1993, 2Pac was convicted of sexual assault. These contradictions have left 2Pac with a complicated yet enduring legacy, but the proud message of "Keep Ya Head Up" remains one of his most powerful. –Dylan Green

Listen: 2Pac, "Keep Ya Head Up"

FFRR

"Inner City Life" wasn't the first jungle tune—the sound was in early creative flush in 1994, when the song was released—but it provided the breakthrough moment for this most British of musical genres and remains jungle's vertiginous peak. On "Inner City Life," Goldie, alongside producer Rob Playford, proved that the style's experimental energy—cut-up drums, bombshell bass, neo-hardcore synths, and dazzling production trickery—could not just co-exist but sit snugly with a vocal from singer Diane Charlemagne that balanced optimism and despair, romance and torment, creating an anthem for youth that was desperate but never hopeless. In the UK, "Inner City Life" grazed the charts and made a star out of Goldie, while jungle would go from strength to strength, dynamiting its reputation as a mere playground for twisted ravers. Twenty-eight years on, the song's amalgam of innovation and soul remains astonishing. –Ben Cardew

Listen: Goldie, "Inner City Life"

Drag City

The atmosphere of "Wild Kindness" is heavy, laden with nitrogen gas and cigarette smoke. It's the last song on Silver Jews’ American Water, the most important album of band leader David Berman's career. As songwriter and a poet, he's at the height of his powers here, at his most fluid, macabre, and surreal. The images jump directly into your mindspace, one after another: grass growing in an ancient icebox, drug store hair dye dripping into a cracked motel sink. At the song's center, Berman tries to wrap his head around what it means to be kind, to watch time slip out of your control. It's a hallucination that begins with terror and ends with transcendence. –Sophie Kemp

Listen: Silver Jews, "Wild Kindness"

MCA

Before "Poison" rocketed them to superstardom, Ricky Bell, Michael Bivins, and Ronnie DeVoe were pretty much only known as "the other guys in New Edition." That gave them the freedom to try out a risky new sound, a groundbreaking blend of R&B and hip-hop that framed the group's vocal harmonies in gritty production. At the time, the casual misogyny of the song's raps were the clearest sign that these guys were done wooing "Candy Girl"s; thirty years later, it's hard to find anything smooth about lines like "the low pro ho she’ll be cut like an afro." But that opening dirty snare roll, now as iconic as "Be My Baby," still finds a way to fill any wedding or bar mitzvah dance floor, regardless. –Jessica Suarez

Listen: Bell Biv DeVoe, "Poison"

Def Jam / PolyGram

At his peak, Method Man wasn't just the Wu-Tang Clan's brightest commercial prospect—he was also the member with the most sex appeal, as his charisma and smooth voice made him a natural for the kind of sultry rap-R&B hybrids that dominated the ’90s. Remixing "All I Need"—a love-centric track from his 1994 solo debut Tical—with Mary J. Blige was an easy call, and "I’ll Be There for You/You’re All I Need to Get By" turned Meth's sweet nothings into an undeniable anthem. As Blige's vocals coast smoothly over samples of Marvin Gaye and Biggie, Meth's bars are affectionate without losing the hard edge that got him there: "You didn't have to funk with me/But you did, now I’m going all out, kid/And I got mad love to give, you my nigga." –Dylan Green

Listen: Method Man, "I’ll Be There for You/You’re All I Need to Get By" [ft. Mary J. Blige]

Parlophone / Capitol

"Let Down" missed out on being OK Computer's lead single only because the band was unhappy with the music video. You can see it, though, right? It's a perfect introduction to the album's themes of automation and alienation: "Transport/motorways and tramlines/Starting and then stopping /Taking off and landing /The emptiest of feelings," Thom Yorke sings, conjuring the lack of control in getting stuck in traffic or sitting in a tin can at 33,000 feet, and the horror of being stuck within one's own body. Modern transportation has gotten bigger, faster, and stronger, and it threatens to overwhelm us humans, crushing us like bugs.

So why, for God's sake, does this song feel so hopeful? Its lullaby melody soars freely in ways the song's protagonist never can, as Yorke's overdubbed counterpoint overflows and overpowers his words. He sings about being "hysterical and useless" while at the same time showing you what it feels like to be free and unbounded. –Jessica Suarez

Listen: Radiohead, "Let Down"

Mo' Wax / FFRR

"Midnight in a Perfect World" nearly caused DJ Shadow's landmark sample tapestry Endtroducing… to be mothballed entirely. Though a rising star for UK label Mo’ Wax, Shadow was beset by self-doubt, and the burden of finding room for (among others) Meredith Monk, David Axelrod, Rotary Connection, and Organized Konfusion to all perch harmoniously on the same five-minute waveform left him vibrating with stress. In the end, those long hours spent recasting ancient glyphs into a language of his own paid dividends: He mastered the art of lo-fi beats to study to two decades before the trope even had a name. And "Midnight" endures as a peerless companion of choice for introverts, stoners, and late-night ponderers because, in that moment of creation, Shadow was all three. –Gabriel Szatan

Listen: DJ Shadow, "Midnight in a Perfect World"

Next Plateau

Like the universe, women's sexuality is expansive, ever-evolving, and predominantly unexplored by man. The distance traveled between Salt lowering her sunglasses and ogling a guy in a three-piece suit on Coney Island beach in 1993's "Shoop" video and Megan Thee Stallion and Cardi B scissoring onstage to "WAP" at the 2021 Grammys, for example, is galactic. Though it might seem quaint in comparison now, "Shoop" was pioneering when it came out, a sex-positive anthem delivered over a reworked Ikettes hook that encouraged women to go after whomever they wanted, however it was hanging, and whenever they wanted it. Salt and Pepa glide over the track with libidinous gusto, sharing punchlines and inventing new ways to flip hetero conquests and objectify the male form. –Emma Carmichael

Listen: Salt-N-Pepa, "Shoop"

Epic

Rarely has a band nailed its sound and agenda from day one like Rage Against the Machine did on its ceaselessly thrilling debut single—not just the blueprint for everything that the Los Angeles quartet would do but the apogee, too. Every component of Rage's musical battlewagon is firmly in place: the rhythm section's wrecking-ball funk, Zack de la Rocha's shattering fury, Tom Morello's Swiss-Army-knife guitar playing. It's enough to fool you into thinking that fusing hip-hop, punk, and metal was easy, although the ’90s would provide numerous counterexamples. De la Rocha's verses targeted the LAPD in the immediate wake of the Rodney King uprising, but he made the song eternal by boiling down decades of protest songwriting into a single personalised roar of denial—"Fuck you, I won't do what you tell me"—that made resistance sound like the most natural, and exhilarating, impulse on earth. –Dorian Lynskey

Listen: Rage Against the Machine, "Killing in the Name"

Big Beat

A rejection the whole world embraced, this rocksteady anthem by Kingston's Dawn Penn has deep roots that still flower today. In 1967, the teenaged Penn sang her song to ska and reggae kingpin Coxsone Dodd, who turned it into a modest hit on the iconic Studio One label. A few more singles followed, but in 1970 she left a music industry she says never paid what she was due. Almost 30 years later, she showed up at producer Clevie Browne and Steely Johnson's studio with a tape; instead, they re-recorded her first recording in a single vocal take. Penn, radiant among golden-hour horns, sounds wise and defiant over the track's crisp swing. By 1994, the cult hit became a new standard, and soon everyone from thickets of jungle producers to the legends of 21st century pop music—Rihanna, Mary J. Blige, even Beyoncé—would say yes to Penn's irresistible hit. As if anyone could possibly say no. –Jesse Dorris

Listen: Dawn Penn, "You Don't Love Me (No, No, No)"

Delicious Vinyl

Thirty years ago, the Pharcyde figured out that silliness can be an avenue into darkness. The L.A. group's defining song, "Passin’ Me By," unfolds as a series of vignettes, the four rappers each telling of a love interest that didn't give them a shot. Producer J-Swift, who was trained as a classical pianist, approaches sampling as a bandleader might, and the track's locomotive bassline lends it a playful, bluesy rumble. It's a fitting backdrop for verses that are undercut by a streak of sadness, like Fatlip getting a "return to sender" notice on his love letter, or Slimkid3 growing older with a girl and watching the feelings fizzle out. Sandwiched between these tales is that cloudy saxophone, a slow sigh that draws you into the song's wistful loneliness. –Mano Sundaresan

Listen: The Pharcyde, "Passin’ Me By"

Sire / Warner Bros.

Discovering the art at Susanne Bartsch's Love Ball in 1989, Madonna was a latecomer to ballroom but a quick study. She made the scene into a pop monument, enshrining the artistry of ballroom in the hetero-mainstream imagination. Over a joyful house beat, co-produced by Madonna and Shep Pettibone, she is as imperious and instructive as Old Way, a capital-M Mother coaching a recruit for the performance of their life, whispering "vogue, vogue, vogue…" over icy synths and Salsoul horns like an invitation to some promised land. "Vogue," a love letter to the balls as a space for self-actualization, was both the first house record to hit number one, and one of the very few Top 40 hits to unapologetically celebrate queer life at the height of the AIDS epidemic. Although Madonna had sung of the material world's luster before, the track conjures a vision of luxe living that feels easier to attain: Beauty is where you find it, and you can be as enchanting as those queens of Golden Age Hollywood, no matter how fat your wallet. You’re a superstar and what's more, you know it. –Owen Myers

Listen: Madonna, "Vogue"

Palace / Domino

Redolent of the beer-fed, Appalachian sort of primitivism that boomed like a rusty gong across Drag City's roster throughout the ’90s, Will Oldham's ballad to feeling bad feels, in an uncomplicated way, totally bathetic. His night vision isn't so much an abstraction as it is a straightforward ability to see the discrepancies between a life internal and a life before those we love. Johnny Cash would cover this song in 2000, in a move so natural that it seems to have been written for him in mind. And why not: Both Oldham and Cash are fluent in the border-crossing between hurt and endurance. Both are aware that pain is no shortcut to profundity. Both know that there is a very small foothold between living with agony, and dying of it. –Mina Tavakoli

Listen: Bonnie "Prince" Billy, "I See a Darkness"

Warner Bros.

Legend has it that Michael Stipe only needed to hear the piano part from "Nightswimming" one time before the entirety of the lyrics appeared to him: the photograph on the dashboard, the shirt left by the water, the indelible image of two moons, side-by-side, in the late-August sky. As he sings the Automatic for the People ballad, accompanied by Mike Mills’ music-box piano and a string arrangement by Led Zeppelin bassist John Paul Jones, it's easy to imagine it occurring as a stream-of-consciousness recitation from somewhere deep in his psyche. After spending the 1980s in more cryptic, agitated moods, Stipe sounded newly romantic and comfortable, the arrangement pared down to a lullaby, the scenic view stretched out before him. "These things they go away," he sings, "replaced by everyday." So he captures it all in the moment, just as it appears. –Sam Sodomsky

Listen: R.E.M., "Nightswimming"

Elektra

Ol’ Dirty Bastard once stole the stage from Shawn Colvin at the Grammys, brought an MTV crew to film him fraudulently claiming a welfare check, and upstaged the Notorious B.I.G. at his own birthday party—all of which made him seem like a professional wrestler who never breaks character. He was a brilliant rapper apart from the antics, possessing a generational oddball charisma that labels and mentors can't teach. Decades of pop music couldn't sum up the vagaries of unrequited love better than the blunt early lines of his 1999 classic "Got Your Money"—"I don't have no trouble with you fucking me/But I got a little problem with you not fucking me"—as he whimpers, roars, and slurs his way through a litany of sleazy come-ons. As the millennium approached, ODB was looking to the past; "Got Your Money" is a lifeline to the 1970s, built around a deceptively simple Neptunes production and comely Kelis hook, and boasting a music video stitched together from old Dolemite clips. The nostalgia was respectful, even if the lyrics were not, but the professionally unprofessional juxtaposition made for an indelible pop-rap song and the biggest single of ODB's solo career. –Jeremy Gordon

Listen: Ol’ Dirty Bastard, "Got Your Money" [ft. Kelis]

Playhouse

Like a handful of the most innovative electronic producers in the 1990s, Frankfurt's Rajko Müller—better known as Isolée—made an anthem that defined a movement. His single, "Beau Mot Plage" brought microhouse, a cool take on four-to-the-floor that favored sound design over soul, to the mainstream—or at least the big rooms of better clubs. The song's expert engineering had a bit in common with the stiffly funky clicks and hissing of the endless 12"s that came in its wake. But unlike most of its imitators, Isolée's track is simply massive. It's precisely hedonist and balances opposing forces expertly: a thick undertow of bass against melodies that spatter like waves cresting with foam; whirlpools of dub and the forward momentum of an irresistible, if slightly submerged, kick drum. And the astonishing rounds of guitar-like pinging—whether sampled or ersatz, who knows—ground "Beau Mot Plage" like a sandbar between past classics like "Sueño Latino" and "Little Fluffy Clouds" and the work of future pleasure seekers like Four Tet and Octo Octa. Prog in structure, pop in sensibility, on this beach microhouse never felt more macro. –Jesse Dorris

Listen: Isolée, "Beau Mot Plage"

Virgin

On the surface, "Together Again" borders on Hallmark-card triteness: It features a childlike, major-key melody, a peppy disco-house beat, and a hook that goes, "Everywhere I go, every smile I see/I know you are there smilin’ back at me." But Jackson wrote the lyric about personal friends she’d lost to AIDS, and the song's co-mingling of plucky cheerfulness and crestfallen grief makes it both winsome and wistful, echoing the spirit of the Supremes’ classic "Someday We’ll Be Together." In 1997, the world was in the second decade of the AIDS crisis, yet few mainstream pop stars had creatively responded to the epidemic, despite the deaths of musicians like Freddie Mercury and Eazy E, and the disproportionate effect of HIV and AIDS on LGBTQ+ communities of color. By paying tribute to the departed, this No. 1 hit became an intervention, a cause—an upbeat rallying cry when we needed it the most. –Jason King

Listen: Janet Jackson, "Together Again"

Electric Honey

If "The State I Am In" didn't already exist, Belle and Sebastian would have to go back and invent it. A former long-distance runner, who struggles with chronic fatigue syndrome, records an album on a shoestring budget with a newly assembled group for a school project, and then sits back and watches as the opening track is rapturously championed by the BBC's Radio 1? The story of the song itself is the type of shaggy-dog tale that the Glasgow band has been delivering with increasing directness for more than a quarter-century since it was originally released on 1996's Tigermilk. With its nonchalantly ambitious ’60s-style chamber-pop ruminations on spirituality, sexuality, and the meaning of it all (or possible lack thereof), "The State I Am In" is also perhaps the archetypal Belle and Sebastian song. For the many who would discover it as the band's music trickled across online forums in the late 1990s, it signified a gentle, sophisticated rebuke to the false post-grunge link between aggressiveness and transgressiveness. It also marked a breakthrough for the self-consciously tender sensibilities of likeminded indie labels such as Scotland's Postcard, England's Sarah, and Olympia, Washington's K. Today, after several decades of twee aesthetics rotating in and out of fashion, it simply sounds like a classic record. No one writes them like they used to, so it may as well have been Belle and Sebastian. –Marc Hogan

Listen: Belle and Sebastian, "The State I Am In"

Mercury

As in New York, Newark, and Atlanta, the underground club scene in Baltimore was intimate. With Crystal Waters’ "Gypsy Woman (She's Homeless)," respected local DJs and producers the Basement Boys were able to transpose the sybaritic vibe of local hot spots like the Black Box to similar musical sanctuaries for Black and gay youth outside Maryland. Their instantly memorable, organ-driven rhythm track combined with Waters’ distinctive, jazz-influenced vocals to create a perfect peak-hour club record. Dancing to serious subject matter is a form of exorcism in house music—and the opening bars of "Gypsy Woman" sent the denizens of New York City's most influential nightclubs running for the dancefloor. –Carol Cooper

Listen: Crystal Waters, "Gypsy Woman (She's Homeless)"

Ruffhouse / Columbia

The Score functions as the rare hip-hop classic that appeals to a cross-generational pop audience without losing its edge: Its iciest posse cuts satisfy the heads, while Lauryn Hill's buttery crooning makes your parents happy. It spawned the smash "Killing Me Softly," a cover of singer-songwriter Lori Lieberman's 1972 song that was made famous by Roberta Flack a year later. The Fugees version is a wonderfully effective crowd-pleaser while remaining strange and subversive, a study of texture and the ways our bodies respond to space. Its most jarring section is the first verse, after that twangy sample, when Hill sings over a sparse, extended breakbeat, her voice cutting through the mix like a hatchet. It's a subtly complex record that maps onto the mysterious arc of the Fugees; just a year after The Score launched all their careers, they’d start to dissolve. –Mano Sundaresan

Listen: Fugees, "Killing Me Softly"

Mute

The crucial thing to understand about Depeche Mode's main songwriter Martin Gore is that he's a moralist with a wide self-critical streak, which means that even in the biggest hit from synthpop's best-selling group, one covered by everyone from Tori Amos and Nada Surf to Breaking Benjamin and Susan Boyle, he insists on being a little creepy. Hence, he undercuts his virtue by calling his beloved "my little girl." Yet he also honors her with the blazingly romantic line "All I ever needed is here in my arms" and by submitting his little harmonium ballad to a majestic dancefloor treatment featuring a sliding, slinky guitar riff for which many rock bands would indeed sacrifice virgins. You can't say this Zen valentine hasn't aged well: While our communication tools manipulate free speech's equality so effectively that we’re destroying democracy worldwide with constant deafening chatter, savoring silence has become more quixotic than ever. –Barry Walters

Listen: Depeche Mode, "Enjoy the Silence"

Underground Resistance

There's something almost sacred about DJ Rolando's "Jaguar," often known as "Knights of the Jaguar." It's not just the cascading synth rivulets, the way the driving Detroit claps somehow gel with the off-time ride, or even the full-body rush that comes when the strings tease in at two and a half minutes—there's something in the way all these elements come together that is truly mystical. Arriving just in time to be an anthem of the 1999 Berlin Love Parade and the first Detroit Electronic Music Festival (today known as Movement) in 2000, "Jaguar" is a melancholy belter that gallops and spirals before ending in a sort of symphonic chaos; you might even say that it's trance in its purest and least cheesy form. Sleek and swift, it's a melancholy epic that you never want to be over—a perfect piece of knight music. –Vivian Host

Listen: The Aztec Mystic, "Knights of the Jaguar"

East West / Lola Waxx

R&B singer Adina Howard's biggest hit serves as a member's pledge for Club Freak: a place where a woman can proudly self-describe as a "dog" and live shame-free in her liberated sexuality. Subverting peacocking rap masculinity over a breezy invocation of G-Funk, Adina leans all the way back in the driver's seat, refusing to pull out her wallet for any man. The song samples Sly Stone and Bootsy Collins, but its finest flip occurs when Howard transforms the squeaked-out Mary Jane Girls sample from LL Cool J's girlfriend-wishlist "Around the Way Girl" into an expression of her own needs: "I got you shook up on your knees." Over the years, "Freak Like Me" has been famously covered by Sugababes and interpolated by Megan Thee Stallion and SZA, continuing to stomp all over whatever's left of the idea of ladylike decorum. –Claire Lobenfeld

Listen: Adina Howard, "Freak Like Me"

DGC

In retrospect, the terms of Rivers Cuomo's Faustian pact were harsh. Can you imagine? After splurging a career's worth of chops and goodwill in one burst, you’re condemned to walk an earth where your possessive, juvenile songwriting drifts further from acceptability while new generations relentlessly clown your Toto covers as virgin music.

But we’ll always have Weezer's glory years, especially "Say It Ain't So," not so much an anthem as an arena wrecking ball swaddled in cringe-resistant cladding and studded with spikes. It's the most relatable Cuomo has ever been; the focus locks on personal minutiae, framed by a letter offering clemency to the absent father who left his psyche mangled in the first place, yet the feelings evoked are universal. As the track creeps to a volcanic climax, each strained syllable and bent note hits with increasing frenzy, daggers plunged deep into an inescapable past. –Gabriel Szatan

Listen: Weezer, "Say It Ain't So"

Priority / No Limit

No Limit Records’ symbol was a tank. And if the label's colonel, Master P, understood anything, it was how to orchestrate an onslaught—of artists, releases, videos, and hooks—in order to overwhelm listeners via brute force and charm. "Make ’Em Say Uhh!" distilled this approach down to a frenzied posse cut featuring four of his strongest soldiers, including the ever charismatic Mia X and the volcanic Mystikal, touting the tank's might over producer KLC's collision of rollicking horn blasts and ominous piano. Yet for all its Louisiana bravura, the song also owed a piece of its sonic soul to Harlem, New York, thanks to P's clever repurposing of the Masterdon Committee's early-’80s electro hit "Funkbox Party" for the hook. Ever the strategist, Master P well recognized that the time-tested tactic of synthesizing influences and making them new again may be the most potent weapon of all. –Jeff Mao

Listen: Master P, "Make ’Em Say Uhh!" [ft. Fiend, Silkk the Shocker, Mia X, and Mystikal]

Virgin

After proving he could fill arenas and headline festivals with the alt-rock epics of Siamese Dream, Billy Corgan wanted more: more noise, more drama, more sprawl, more chaos. His pursuit of more beauty yielded "1979," an attempt to bottle up the bliss and abandon of youth in four minutes of sentimental pop. Corgan wrote the song in his late 20s, and its classic video captures a day in the life of a disaffected suburban mallrat fondly remembered a decade later. After touring your hometown from a cramped backseat, pinballing through a house party, and stopping for snacks in a fluorescent convenience store, "1979" sounds like the final drive home, quietly hurtling through an inky night lit by halogen street lamps. It's nostalgic without an ounce of bitterness, and it only grows more poignant as those teenage memories fade in the rear-view mirror. –Jamieson Cox

Listen: Smashing Pumpkins, "1979"

Big Life

As the UK's first chill-out DJ, former Killing Joke roadie Alex Paterson soothed clubbers with an ecumenical blend of musical oddities. That philosophy informed his defining single as the Orb—ambient house's ground zero. Rickie Lee Jones dreamily recalls 1960s Arizona skies while BBC presenter John Waite rhapsodizes about the English summer. Ennio Morricone's harmonica confers with a decelerated Harry Nilsson beat and the scintillating multi-tracked guitars of Steve Reich via Pat Metheny. While fellow sample-hounds Bomb the Bass and S’Express crafted hectic smash cuts of dancefloor commandments, Paterson and co-producer Youth (Killing Joke's former bassist) liquefied their source material into a benign reverie, propelled by a cheerful acid-house burble. This aesthetic—English whimsy meets big-sky American romance—is also at play in the KLF's ambient road trip Chill Out, but "Little Fluffy Clouds" condensed it into pop, finally cracking the UK Top 10 upon its re-release in 1993. –Dorian Lynskey

Listen: The Orb, "Little Fluffy Clouds"

EMI Latin

You know the drill: Your heart swells, your hands sweat, and a stutter seems to appear out of nowhere. It's that feeling of a simmering crush that Selena bottles on "Bidi Bidi Bom Bom." The husky, melismatic "yeah" that opens the song is a reminder that Selena's voice was just as suited for singing about forbidden love and breakups as it was for the thrill of crushing hard. Every element here is designed to produce effervescence, evoking the fast heartbeat of infatuation: the wobbly reggae guitar, the steady cowbell, the pulsing cumbia rhythm. That isn't accidental; as the story goes, Selena made up a rhyme about a fish swimming in the sea during a soundcheck one day, and eventually "Itty Bitty Bubble" turned into a full song. While the Tejano star's tragic mythos and cultural martyrdom often threaten to consume her legacy, "Bidi Bidi Bom Bom" is a small slice of the whimsy and joy she left behind. –Isabelia Herrera

Listen: Selena, "Bidi Bidi Bom Bom"

Bad Boy / Arista

When "Mo Money Mo Problems" arrived in the summer of 1997, Diana Ross’ hiccupping sample and Kelly Price's sashaying lamentation as ubiquitous as a heat wave, Biggie Smalls had been dead for four months. Mase and Puff Daddy—then nearing the release of their respective debuts—took the lead, playfully plodding through opening verses and goofing on Tiger Woods and Bryant Gumbel in a paradoxically ostentatious video. In that life-after-death context, it was impossible not to hear the song's tragic irony, like a warning by and for B.I.G. about the fate that may await such a contentious and ostentatious superstar. But the anthem's enduring power stems from its moral simplicity, epitomized by Biggie's monstrous minute-long verse, buried in the second half: Stay true to your roots and crew, even as you aspire for the cover of Fortune. This was never a song about dying or problems, really; it was a song about living through a moment's madness, of making it out intact and sane. –Grayson Haver Currin

Listen: The Notorious B.I.G., "Mo Money Mo Problems" [ft. Puff Daddy and Mase]

Proudly celebrating one's mediocrity was the defining pose of the 1990s, and Beck's breakout hit was a national anthem for the prevailing mood. "Loser" checked every box for a singalong radio smash, embodying the particular combination of apathy and dry cleverness that made the losers in your life seem inordinately charming—a depressed singer might have asked "Why don't you kill me?" but in the rapper-rocker-singer's mouth, it came off like a bored dare. Beck claimed that the verses of cryptic wordplay were freestyle nonsense in an attempt to rap like Public Enemy's Chuck D, but all of his intents and purposes snapped together on that battlecry chorus. Or maybe he just stumbled into that, too—he wouldn't be the first of Gen X's stereotypically and stoned layabouts to fuck around and find transcendence. –Evie Nagy

Listen: Beck, "Loser"

LaFace / Arista

The lead single from Toni Braxton's sophomore set Secrets is perhaps best remembered for its playful video: When Braxton isn't gyrating in a skin-tight white catsuit, she and sitcom gal pals Vivica A. Fox and Erika Alexander size up handsome dudes as they ride up an elevator shaft. The R&B tune—a collaborative effort between Braxton, Babyface, and Bryce Wilson of Groove Theory—skillfully captures the feeling of unbridled lust. Its bass-heavy beat oozes along at a blunted tempo, evoking both ’70s Barry White and ’80s Steve Arrington, as Braxton sings a lyric racier than anything we’d heard from her before: "I can imagine you touching my private parts." The real centerpiece is her sultry, thick-as-molasses alto—no vocalist of the ’90s better embodied the allure of body heat. –Jason King

Listen: Toni Braxton, "You’re Makin’ Me High"

Motown

In just over four minutes, Queen Latifah takes on street harassment, misogyny, domestic violence, and gangster posturing—and manages to make it all sound more like a block party than a term paper. From the start of her career, she made music that centered Black women's perspectives and experiences, putting them in direct dialogue with her male counterparts. With "U.N.I.T.Y.," she directly addresses her Flavor Unit crewmate Apache, whose controversial "Gangsta Bitch" had come out earlier in the year; her opening challenge, repeated throughout ("Who you callin’ a bitch?") invites yet another response. The song sits comfortably in its unabashed politics, and in her flow: melodic, authoritative, undeterred. –Emma Carmichael

Listen: Queen Latifah, "U.N.I.T.Y"

Matador

If you take the phrase "greatest hits" very literally, the everlasting version of Guided by Voices’ "Game of Pricks" is the punchy, professional recording from 1995's Tigerbomb EP, eventually included on the band's best-of compilation—a song built for pumping a fist with a beer in the other hand. But underneath GBV's bullish exterior as the best Midwestern bar band to ever live was an insular and vulnerable core, fomented as songwriter Robert Pollard struggled to find artistic success while working as a schoolteacher in his native Dayton, Ohio. That side of GBV bled through the scratchy version of "Game of Pricks" from Alien Lanes, the hoped-for breakout record that allowed them to quit their day jobs before the presale numbers came in. With the bass turned all the way down and the treble turned all the way up, Pollard's song sounds like a private letter to a younger self, a crunchy bedroom-pop nugget built around a self-affirming message worth stenciling into your high school notebook: "You can never be strong/You can only be free." Guided by Voices never made it big, it turned out, but success doesn't matter when you know yourself this well. –Jeremy Gordon

Listen: Guided by Voices, "Game of Pricks"

One Little Independent

Björk is not an alien, despite the extraterrestrial terms in which she is often described. But as a human woman who, at the time of her 1993 solo debut, baffled journalists simply by being from Iceland, to say nothing of her avant-garde sensibilities, she was well-positioned to offer an outsider's perspective on "Human Behaviour." On the surface, her thesis—that we definitely (definitely, definitely) lack logic—is a warning to other interlopers preparing for contact. Really, it names our vagaries, our capacity for misunderstanding and being misunderstood, as essential to the human condition, reframing these isolating experiences as shared ones. Furthering the song's sense of universality, Björk reached across time and geography to borrow its rattling percussion and commanding timpani riff from the Brazilian composer Antônio Carlos Jobim. The result, the throat-clearing opening of Björk's foray into experimental dance-pop, is strange and welcoming; it invites you to sit with the unfamiliar. –Olivia Horn

Listen: Björk, "Human Behaviour"

Mango / Taxi

"Murder She Wrote" is a testament to taking your time on your craft. Dancehall duo Chaka Demus and Pliers spent five years working on the song, a natural occurrence in Kingston, Jamaica, where producers would record dozens of versions before landing on the one with enough of the genre's brash and ineffable blend of memorable lyrics and high-speed rhythms. "Murder She Wrote" was exactly that, a speaker-cracking track that became one of the biggest hits from the ’90s dancehall scene. Built around a riddim inspired by Indian bhangra music and Toots and the Maytals’ 1966 track "Bam Bam," the song was among the first of its kind to break through in the United States by finding a strong foothold on radio, where that instantly recognizable opening bassline began to wind its way through the country. "Murder She Wrote" has been endlessly interpolated since, but the original is eternal, a staple of sweaty summer block parties everywhere that further pushed the genre forward to international attention. –Eric Torres

Listen: Chaka Demus / Pliers, "Murder She Wrote"

Flipmode / Elektra

There are a million ways a rapper might approach the beat to "Put Your Hands Where My Eyes Could See." Sourced from a dusty album cut by 1970s soft-rock hitmakers Seals & Crofts, it consists primarily of negative space: a stuttering bit of bassline here, a snare hit or two over there, but otherwise a blank canvas, its minimalism an encouragement for a vocalist to try out any flow they’d like. A less inventive rapper might have chosen to fill the dead air with words, to keep the rhythm rolling along when the production threatens to sputter out. Busta Rhymes took the opposite tack, cutting off his stream of syllables to emphasize the emptiness that opens up on the fourth beat of every bar. With its periodically muted bursts of virtuosic precision, "Put Your Hands Where My Eyes Could See" moves like a malfunctioning robot, or a clip of a breakdancer that someone keeps pausing and playing again. It's the sound of a rapper who was usually the loudest voice on any given track discovering the power of silence. –Andy Cush

Listen: Busta Rhymes, "Put Your Hands Where My Eyes Could See"

DGC

What's the point of being cool? Mostly nothing, Kim Gordon's deadpan monologue suggests. Ostensibly a shot at LL Cool J, whom Gordon had interviewed for Spin and failed to connect with, "Kool Thing" flies at the edge of control, part go-go rave-up, part ideological exorcism. It's a song coated in sarcasm so thick, it's almost impossible to crack it—just listen to the way the guitars tag every line in the verse with an acidic shoulder shrug. But the fed-up ecstasy that crowns Gordon's spoken bridge makes it sound as if Sonic Youth, already well-aware of their fate to be the eternal avatars for a certain kind of white alt-cool by the time they’d recorded this song, had crashed into irony's outer wall. The song itself is their attempt to navigate the rubble. –Marty Sartini Garner

Listen: Sonic Youth, "Kool Thing"

Arista

Among the most evocative acts of New York's mid-’90s major-label hip-hop boom, the Bronx duo Camp Lo blended Harlem Renaissance verve with Blaxploitation-era sizzle. The sole single from their debut album Uptown Saturday Night, "Luchini AKA This Is It" distills Sonny Cheeba and Geechi Suede's dynamic energy and vivid—at times impenetrable—vernacular. The song's heavily referential verses unfold like the ecstatic denouement of a heist film, replete with silk shirts, Italian liqueurs, and sumptuous island getaways. Built around a two-bar horn sample from Dynasty's luxurious 1980 R&B track "Adventures in the Land of Music," Ski Beatz's production captures the rush of 125th Street across its various heydays. Only a group as bold as Camp Lo would dare kick off their career with a victory lap. –Pete Tosiello

Listen: Camp Lo, "Luchini AKA This Is It"

Wild Bunch / Virgin

The reincarnation of Bristol's Wild Bunch collective, Massive Attack brought their hometown's full range to bear on their 1991 debut album, Blue Lines: hip-hop breaks, dub basslines, a rolling hint of house music, and a healthy dose of soul, thanks to their singer, Shara Nelson. But for "Unfinished Sympathy," they looked beyond the traditional trappings of soundsystem culture. Tracking Nelson's verses first against a single drum machine, then adding breaks, samples, and scratching, the group ended up getting the synth parts re-recorded by a full orchestra at Abbey Road Studios, dialing up the song's already cinematic properties and yielding a breakbeat soul classic of epic proportions. The strings may have marked an early instance of rough-and-ready rave culture going upmarket, paving the way for a host of dubious techno-goes-to-the-symphony projects in the decades to come, but "Unfinished Sympathy" remains shot through with a murky urgency that refuses to clean up nicely. –Philip Sherburne

Listen: Massive Attack, "Unfinished Sympathy"

A&M

From Pride parades to Fire Island, from The Adventures of Priscilla, Queen of the Desert to the Palladium, it's not a party without "Finally." The early ’90s airwaves pulsed with glossy Eurodance, but "Finally" was different—a house track firmly in the Chicago house tradition, with Peniston not as a disposable rent-a-diva but as the fully realized personality at the center. The singer was working retail and doing support vocals on the side when A&M tapped her for a single. She took the lyrics from a poem she wrote in college and turned them into "Finally," her first and best-known hit, a self-fulfilling prophecy enabling her to live out her dreams. Between the sunny tea dance-ready beat and chorus, and the way Peniston belts, growls, and scats her way through it, "Finally" has become a true anthem for finding community, romance, embodiment, desire, self-confidence, or whatever else might have felt unattainable for way too long. –NM Mashurov

Listen: CeCe Peniston, "Finally"

Kill Rock Stars

The second song from the third album by the Pacific Northwest trio Sleater-Kinney was the moment when the explosive alchemy of their post-riot grrrl power trio truly coalesced. Before, guitarists and songwriters Corin Tucker and Carrie Brownstein had primarily sung separately. But here—in a song about their own painful romantic separation, we would eventually learn—they came together, braiding their voices more devastatingly and ecstatically than ever. The tension of Tucker's aching vibrato holding on alongside Brownstein's clipped delivery is the image of realism in parting. "One More Hour" described one relationship's end, but it became a beginning, a breakthrough break-up song that bound Brownstein and Tucker together in beautiful friction. –Jenn Pelly

Listen: Sleater-Kinney, "One More Hour"

LaFace

"Rosa Parks" isn't the best song on Aquemini (that's "SpottieOttieDopaliscious"), nor was it OutKast's biggest to date (that was "Elevators (Me and You)"). But at a moment when labels like No Limit and Cash Money were trying to preserve Southern rap's regionality while building a national audience, the track's hollering and harmonica felt like provocations toward listeners who wouldn't be caught dead in something so country. And while the extraterrestrial imagery connected them to Afrofuturists like Parliament and Jimi Hendrix, it doubled as a joke about how most Americans imagine the rural South as another planet anyway. –Mike Powell

Listen: OutKast, "Rosa Parks"

Kedar / Universal

Mere months after lifting neo-soul to new heights with her 1997 debut Baduizm, Erykah Badu had the sheer confidence to release a full live concert album that included many of those same songs. It was a runaway hit, thanks in large part to the non-album radio single "Tyrone." The titular proto-scrub was the buddy of Badu's man, who never paid for anything and always brought his dirtbag pal along with buddies Jim, James, and Paul to everything they did together. Badu was always covering their asses, which is why she suggested her guy better call Tyrone to help get his shit out of her house, her voice oozing with raw, mesmerizing, sexy-as-hell contempt. The kicker—"But you can't use my phone"—was a lyric that made exhausted girlfriends the world over scream with delight, and pledge devotion to the church of Baduizm for life. –Evie Nagy

Listen: Erykah Badu, "Tyrone (Live)"

Mo' Wax

When it debuted, Carl Craig's "Bug in the Bass Bin"—the first outing under his Innerzone Orchestra alias—sounded like nothing else in Detroit techno, or anywhere else, for that matter. Skilled in the dark arts of razor and tape, Craig sliced into a 1960s easy-listening percussion album to come up with the song's distinctive beat: a rolling, sliding brushed-snare pattern whose sluggish feel he accentuated with queasy synth glissandi. There's no discernable downbeat; woozy and ghostlike, it half-slinks and half-floats across the dancefloor. The principal riff is just a call-and-response between a plucked bass note and a few splashes of synths; the whole thing is humid, hazy, hard to get a fix on. Yet UK DJs like Fabio, attuned to the track's unconventional breakbeat energy, ended up pitching it up to 45, where it meshed with the double-time sounds of jungle and drum’n’bass. –Philip Sherburne

Listen: Innerzone Orchestra, "Bug in the Bass Bin"

Parlophone / Capitol

In its own detached way, "Karma Police" is structured as a stealth microcosm of the first decade of Radiohead's recording career. Its first two minutes are classic ’90s Radiohead: tuneful and sardonic pop-rock, a bit too dour to fit in with the Britpop craze, yet melodically bright enough to be covered by college kids at open mics for perpetuity. Its haunting final refrain imperceptibly sums up an album's worth of alienation in seven words: "For a minute there I lost myself." And its remarkable outro, created by Thom Yorke and Nigel Godrich after the singer told his producer he disliked the latter half of the song, deconstructs it all in a collapsing fizz of samples and noise. "It was the first time we did anything like that," Godrich later recalled—a foreshadowing of Radiohead's restlessness and their growing interest in outré electronics. –Zach Schonfeld

Listen: Radiohead, "Karma Police"

Monument

Six years before The Chicks made "Wide Open Spaces" the title track of their major-label debut, it was just an idea in a notebook belonging to a college student named Susan Gibson. Gibson had written the song in frustration: Everyone in her life seemed intent on making decisions for her, so she wrote what would become one of country's defining feminist anthems in just 20 minutes—a song that saw boundless potential for self-determination in the genre's history of open road romanticism. Years later, The Chicks turned it into a verdant daydream of a bluegrass song, all sighing pedal steel and resolute sisterly harmonies, and it became the emotional blueprint for a career filled with songs about the treacherous, rewarding work of striking out on your own. "Wide Open Spaces" remains a monument to everything The Chicks wanted to see in the world; the career that followed made good on that promise, and then some. –Shaad D’Souza

Listen: The Chicks, "Wide Open Spaces"

Kif Recordings

In an era of over-the-top French filter house (and over-cranked music in general), Pépé Bradock came through with a second-wave deep-house classic whose dusky palette and earworm grooves made it a staple of DJ crates from Detroit to Berlin. Bradock sails into the sunset on a small but mighty romantic string loop lifted from Freddie Hubbard's 1979 mellow jazz number "Little Sunflower," further propelled by hip-shaking tambourines (sampled from Max Roach's "Driva’ Man") and a strong, heartbeat-like 125-bpm kick drum. For just over nine minutes, he teases different melodic themes but never loses the utterly hypnotic groove—it's simple and deep at the same time, a song that instantly becomes the perfect soundtrack to any experience. –Vivian Host

Listen: Pépé Bradock, "Deep Burnt"

Afterrmath / Interscope

After leaving the Death Row empire in 1996 and releasing a couple of projects that landed with a thud, Dr. Dre's ongoing relevance was far from secured as the 20th century drew to a close. His redemption came in the form of a hit that connected eras. With its pristine strings and a blinging piano loop, "Still D.R.E." felt like the future. This ultra-high-end form of beatmaking established the template for the Dre-produced hits by 50 Cent, Eminem, and Eve that crushed early 2000s MTV; they’re the kind of productions from which you could launch a luxe brand of headphones. But with Snoop Dogg in the passenger's seat, Dre also drew a line directly back to his G-funk past. It's the type of song that's monumental enough to cement a musical legacy, then, now, and forever. –Dean Van Nguyen

Listen: Dr. Dre, "Still D.R.E." [ft. Snoop Dogg]

Creation / Sire

Commentary on My Bloody Valentine tends to focus on the guitar sound—its swarming amorphousness, the way it's simultaneously soft as snow and hard as nails. Nicknamed "glide guitar" by its inventor Kevin Shields, it's generated by a technique of fast strumming through sustained tremolo and a studio effect known as reverse reverb. But MBV's swoon-power, their unmatched ability to make you sway and flutter your closed eyelids, comes as much from the breathy vocals of Shields and Bilinda Jayne Butcher. The Irish-English group liked to talk about their "not-really-there sound"; on "Only Shallow," Butcher really does sound barely there, a palimpsest of a person wiped out by sensations beyond verbalizing. There are lyrics, but you can hardly make out a word as Butcher's vocal texture blurs into the surrounding wooze. The opening salvo on the shoegaze classic Loveless, "Only Shallow" showcased another of the band's under-discussed strengths: melody. Scores of underground rock groups were doing excruciatingly extreme things with guitars in the early ’90s, but nobody melded tuneful and torrential as exquisitely as My Bloody Valentine. –Simon Reynolds

Listen: My Bloody Valentine, "Only Shallow"

Jive

The cypher is one of hip-hop's most sacred traditions and one that defined the relationship between A Tribe Called Quest's Q-Tip and Phife Dawg. Their chemistry was defined by the way their voices, sense of humor, and nuggets of wisdom informed and clashed with one another, and "Check the Rhime," a highlight from their second album The Low End Theory, is when the two were most in sync. Forget the litany of all-time great quotables, and the minimal bass thump that works its way through your body like a virus. The pleasures of "Check the Rhime" can all be traced back to a timeless chant, the call-and-response between two friends heard ’round the world: "You on point, Phife?/All the time, Tip." –Dylan Green

Listen: A Tribe Called Quest, "Check the Rhime"

Island

The genius of "Rid of Me" is its performance of feminized sexuality. Here's Harvey, a girl who lives on a sheep farm in rural England, shrieking about being inescapable and wanting someone to lick her legs. She's at the peak of her career with a hit album, being as much of a disaffected freak as possible. She sexualizes herself because she can, and the song is deliberately interested in messing with the male gaze, of asking for sex so directly that she almost seems like the Exorcist girl, mid-exorcism. "Don't you wish you never, never met her," she repeats, unflinching, throughout the song over sparse electric guitars and the occasional crash of drums. Also: "I’m going to twist your head off, see." She's not joking. –Sophie Kemp

Listen: PJ Harvey, "Rid of Me"

BMG / Arista

The piano intro of "Walking on Broken Glass" sparkles like a chandelier exploded across a ballroom floor, its crystalline notes falling in sugary shards. Annie Lennox sounds confident as she marches across them on the second track to her solo debut Diva. Carried by Annie Lennox's silky voice, the song rides intoxicating highs and tragic lows; a string section offers an air of formality around a steady synthetic pop rhythm and a punchy guitar part tucked in the mix. Lennox opens up from her level-headed start into a belted chorus, finding brief deliverance before admitting to the excruciating discomfort of trying to hold it together. Even as she stands among the splintered pieces, the emotional undercurrent of "Walking on Broken Glass" captures the exasperation, ache, and yearning of not giving up just yet. –Allison Hussey

Listen: Annie Lennox, "Walking on Broken Glass"

So So Def

The original version of the Ghost Town DJ's Miami bass classic "My Boo" was a dancefloor banger beloved by breakdancers and club kids but not exactly a breakout hit. The track didn't take off until Chicago house legend DJ Mike "Hitman" Wilson put out his remix, with an extended three minutes of atmospheric groove over Virgo Williams’ haunting vocals. The DNA of "My Boo" runs across generations, from the Diplomats to a wobbly remix from witch house wunderkind Balam Acab. But the song is for dancing—it got a deserved second life when two kids from New Jersey started the viral Running Man challenge in 2016. 20 years after the original release, "My Boo" went from an IYKYK classic to a household tune. –Samhita Mukhopadhyay

Listen: Ghost Town DJ's, "My Boo (Hitman's Club Mix)"

Ruthless

The original "Crossroad," recorded during the sessions for Bone Thugs’ sophomore album E. 1999 Eternal, was a somber take on the group's menacing Midwestern funk and a tribute to their late friend Wally Laird. The second version, a plainspoken hymn written in the wake of Eazy-E's 1995 death, became the quartet's first and only No. 1 hit. The synthesis of gospel chords and a subtle Isley Brothers sample lends the effect of a Greek chorus: The rappers hand off brief sing-song verses like sprinters passing a relay baton. Krayzie Bone—a fourth-generation Jehovah's Witness—is the vocal and emotional anchor. In contrast, Bizzy Bone's erratic, unenunciated bars carry the mystique of a camp revival. The song's visceral anguish ("Can somebody, anybody tell me why/I don't wanna die?") and audacious faith offers a universal comfort and companionship in the face of the unknown. –Pete Tosiello

Listen: Bone Thugs-N-Harmony, "Tha Crossroads"

RCA / BMG

"Torn" is the happiest sad song in the ’90s MTV canon, the "Soak Up the Sun" of "Paper Bag"s. Natalie Imbruglia, with her silvery little-girl-blowing-bubbles voice, radiates a totalizing innocence even as she sings about an affair that ended in abject shame and devastation. The contradiction turned "Torn," which was originally recorded by the Danish singer Lis Sørensen in 1993, into an abiding classic: Those opening chords dawn like a sunny day in a cartoon, and then, before you know it, our girl is (allegedly) naked, speechless, bound and broken on the floor. The indelible post-chorus guitar wail was the last-call round at the end of Imbruglia's bender—a source of uncountable interpretive dance interludes past, present, and future, for as long as karaoke and the absurdity of heartbreak coexist. –Jia Tolentino

Listen: Natalie Imbruglia, "Torn"

Untouchables / Elektra

In 1990, Mount Vernon, New York native Troy "Trouble T Roy" Dixon died in a freak accident while on tour with Heavy D & the Boyz. When his Westchester neighbors Pete Rock and C.L. Smooth went about eulogizing him with "They Reminisce Over You (T.R.O.Y.)," they accomplished something even grander and more profound. Barely into their 20s, Pete and C.L. were already casting back: Pete into his parents’ vinyl collection, C.L. into a rough-and-tumble childhood. The warmth of Pete's early work is turned up like an electric blanket here, as he threads a hooky sample of jazz saxophonist Tom Scott through rattling snares. C.L.'s clear-eyed verses match the track's wistful nostalgia, as if he's flipping through a yellowed family photo album. In the end, Trouble T Roy is an incidental character; "T.R.O.Y." considers the rush of life, the embrace of death, and the unifying force of love from the vantage of evaporating youth. –Pete Tosiello

Listen: Pete Rock / C.L. Smooth, "They Reminisce Over You (T.R.O.Y.)"

Blanco y Negro / Atlantic

UK duo Everything But the Girl were reeling from a career-tanking flop of an album when Todd Terry's remix launched all three of them into unstoppable global airplay. That Terry's take on "Missing" had so much octane in the mid-’90s market speaks to the fluidity and hunger for variety from that era's radio programming. Deep dance tracks cultivated by far-flung collaborators could be mammoth hits, as likely to ring out in a club as a CVS; former sophisti-pop darlings from Northern England could meld minds with a house virtuoso from Brooklyn and throw sparks across the globe. Tracey Thorn's voice, let loose from its typical acoustic furnishings, aerosolizes into a fine mist against Terry's galloping loops. In his mix, her words scale up from quiet reflection to existential yearning: a missing so deep it’d take an ocean to fill. –Sasha Geffen

Listen: Everything But the Girl, "Missing (Todd Terry Remix)"

Roswell / Capitol

After decades of his dutiful service as Real Rock's most enthusiastic diplomat, it can be hard to remember a time when Dave Grohl was still trying to figure out what he wanted Foo Fighters to be. So how about this: a guy rooted in mid-’80s D.C. hardcore borrowing half of Sunny Day Real Estate to make a googly-eyed power ballad about his girlfriend, directly and immensely influencing bands like The Get Up Kids and Jimmy Eat World and their subsequent masterpieces. Foo Fighters, the Band Who Broke Emo? Call it a stretch, but the exalted status of "Everlong" is entirely due to Grohl submitting to impulse, drunk in love and swerving far from the middle of the road he's occupied ever since. As a worthy crush should feel, "Everlong" is paralyzing and exhilarating at the same time, its relentless propulsion and professional polish working in tandem to create an illusory effect, like watching an Olympic speed skater furiously pump their legs while appearing to effortlessly glide. That Foo Fighters haven't revisited this sound only underscores its resonance as a song that desperately tries to capture a moment when things feel like they can't possibly be this good again—because they never will be. –Ian Cohen

Listen: Foo Fighters, "Everlong"

DGC

Courtney Love has described "Violet" as a "hex" on a man—purportedly Billy Corgan of Smashing Pumpkins—who wronged her. The feverish lyrics are about assault, exploitation, and the asshole who walks away once he's taken everything he wants from a woman. It is the most frenzied statement on Live Through This, with a force that connects like a fist hitting a brick wall thanks to its hopped-up guitars and a chorus that's screamed more than sung. "Violet" is one of the finest expressions of what Love was capable of in this unbelievably productive period, a woman spinning all her vulnerability, destitution, disgrace, power, speed, sex, rage, and violence into a ferocious incantation. –Alex Frank

Listen: Hole, "Violet"

Champion / Big Beat / ZYX

Good jams never die—they await rediscovery in our bedrooms and train rides, one conversion at a time. Beyoncé understood this adage when she recorded this year's "Break My Soul," dependent on 1993's pop-house hit "Show Me Love." In its original 1990 version, the track sported electric piano, vocoder, and synthesized string parts closer to the post-disco in which Lisa Stansfield specialized. It awaited an essential remix by Swedish DJ-producer StoneBridge, who added the Korg M1 bassline that both time-stamps and immortalizes it. As for the singer, Robin S. sounds like a regular person, like you and me giving the performance of our lives. Dance music often requires anonymity, the better to project our needs. But Robin's hoarse, crinkly delivery (thanks to the flu, she has said) expressed the agony of listeners who tried dancing their way out of their constrictions. "Baby, if you want meeee," she growls before the chorus. Ah, such a fleeting thing, desire. –Alfred Soto

Listen: Robin S., "Show Me Love"

Ruff Ryders / Def Jam

If you’ve ever fought in front of a crowd (and don't go starting if you haven't), you know how much benefit there can be in having your own cheering section. That's the energy DMX brought to "Ruff Ryders’ Anthem," as a chorus of voices punctuated every confrontational line with an emphatic "WHAT!?"

By 1998, New York rap had spent a few years enthralled with mafiosos, lavish lifestyles, and shiny suits, then came DMX—gritty, growling, on a rampage. His biggest-ever hit is grounded in trauma ("All I know is pain, all I feel is rain/How can I maintain with mad shit on my brain?") but never lacking in pure bravado ("Light it up like a candle just ’cause I can't stand you"). The rapper's breathless verses fill in the space around producer Swizz Beatz's spare, Casio-keyboard sound, which was novel in its simplicity. As for the hook, well, childhood fire safety drills were never the same again. –Mychal Denzel Smith

Listen: DMX, "Ruff Ryders’ Anthem"

Kill Rock Stars

Before Sufjan Stevens inspired an army of whisper-voiced acoustic strummers, before Phoebe Bridgers presided over the fetishization of capital-S Sadness, there was Elliott Smith. One of his most enduring tunes, owing both to its prominent slot on the Good Will Hunting soundtrack and covers by artists as varied as Madonna and Beabadoobee, "Between the Bars" conceals its desperate melancholy within a lilting melody that never stops moving forward. Like all of the late songwriter's best songs, this one contains layers; what seems at first like a comforting lullaby to a troubled lover reveals itself, on repeated listens, to describe the seductive promise of alcoholism. "Drink up, one more time/And I’ll make you mine," Smith croons, like the world's most brutally honest beer pitchman. –Zach Schonfeld

Listen: Elliott Smith, "Between the Bars"

Stockholm / Mercury

"Lovefool" makes desperation sexy. In the hands of Swedes Nina Persson and Peter Svensson, the crippling embarrassment of trying to save a failing relationship is considered with the carefree elan of a model on vacation. The biggest single by the Cardigans does pop desire differently: it's about how exhilarating and purely fun it can be to debase yourself in the name of love. (Its popularity in the U.S. is owed, in part, to its placement in both Cruel Intentions and Romeo + Juliet, two films that explore, in backwards ways, the ecstatic nihilism of pursuing a crush.) Persson's vocals, all coquettish sighs and blissful coos, suggest that there's more joy to be found in the pursuit than the goal as she delivers her plea with a cartoonish, IMAX-sized wink. Animating the whole thing is a gorgeous, candy-colored daytime disco stomp—a beat so undeniable that it could turn any relationship death march into a parade. –Shaad D’Souza

Listen: The Cardigans, "Lovefool"

Point Music

When the cellist, composer, and producer Arthur Russell died in 1992, he left behind a pile of music so big that archivists are still sifting through it. There was a little bit of a lot of different things: disco, country, post-minimal "classical" pieces, the spacey beginnings of what we think of as bedroom pop. His genius lived in how many seemingly unrelated points he managed to connect—a vision of creativity more familiar in our curatorial era than it was when Russell was alive. So when you listen to "This Is How We Walk on the Moon," from 1994's Another Thought, first ask yourself what it is. Deconstructed folk? With dissonant electronic vocal processing in the middle? And a salsa-ish trombone part toward the end? Then realize that, as a lifelong Buddhist, he seemed more interested in explorations than conclusions. "This is How We Walk on the Moon" is the sound of sound changing. –Mike Powell

Listen: Arthur Russell, "This Is How We Walk on the Moon"

Death Row / Interscope

If Dr. Dre's G-funk was marked by its hydraulic lurch, his little step brother Warren G's version was more like a sophisticated slide. His biggest hit's understated swagger, and the ease with which the bad-night-goes-good tale unfurls, renders the narrative violence beside the point—it's all seen through the dewy lens of whatever swell things went down later on at the Eastside Motel. Besides, the beat is so slick, it would be impossible for any sense of menace to stick to it in the first place. Gritty? Of course. But the Michael McDonald sample makes it clear: This is Long Beach yacht rap. –Marty Sartini Garner

Listen: Warren G / Nate Dogg, "Regulate"

Warner Bros.

By 1999, all of Doug Martsch's mildest dreams had come true. Built to Spill, his scrappy Idaho band, had steered its way into the waiting arms of a major label, which had handed him the money and freedom necessary to make a classic—1997's Perfect From Now On—and the experience nearly broke him. "Carry the Zero," from two years later, is the sound of a band that has just turned the corner on making a masterpiece. The interplay is still telepathic, the juices of exhilaration are running high, and out pour creations that would never otherwise slip out with such ease. "Carry the Zero" is an exhalation: warm, open-hearted, emotionally generous. Martsch's voice, a keening wail that reaches so high it seems to be vying for airspace with his soaring leads, unleashes a series of cutting observations that somehow land like pure tenderness ("You’ve become/What you thought was dumb/A fraction of the sum"). Instead of the careful patchwork of Perfect, "Carry the Zero" swirls like some kind of dizzying carousel ride: Brett Nelson's bassline leaps up and down the scale like a calliope, Scott Plouf's drums explode like county fair fireworks, and Martsch, the humblest of all of indie rock's many charisma-averse guitar hobbits, soars and glitters above us, a million brilliant shades of emerald and vermillion. –Jayson Greene

Listen: Built to Spill, "Carry the Zero"

KDJ

Paradoxically, you can tell Kenny Dixon Jr., aka Moodymann, is a musician by the way he utilizes samples—not just looping or pasting them in, but interpreting them. "Shades of Jae" is the ultimate example: A lolling Bob James keyboard line and a bit of Marvin Gaye's live version of "Come Get to This" float like wisps of smoke, interacting fleetingly in places and closely in others, but rarely in the same way twice. That teasing quality is shared by the beat itself: The kick drum, house music's traditional cue that it's time to dance, comes in only when Moody feels like it. But he teases us so deliciously, and the groove is so resoundingly right-there without it, that if you can resist moving fully to the whole thing you might be in a body cast. –Michaelangelo Matos

Listen: Moodymann, "Shades of Jae"

Arista

By the end of 1992, Whitney Houston had become pop's golden child, set to star in her first feature film, The Bodyguard. All she needed was a signature soundtrack ballad, and she found it in Dolly Parton's rustic country ballad from two decades earlier. Originally written about Parton's creative split from mentor Porter Wagoner, "I Will Always Love You" was recast under Houston's spell as a heartfelt send-off to a love that's tender but incomplete. Though she had made a career out of vocal exhibitions, this is the Jersey church girl at her most controlled. The song opens softly, then builds with creeping intensity, her voice carving canyons and shifting timbres along the way. The gut punch is that four-second pause and the chilling high note from beyond that blows you to the back of the room. Staying at No. 1 on the pop chart for 14 weeks, "I Will Always Love You" is the best-case scenario of a powerhouse in command. –Clover Hope

Listen: Whitney Houston, "I Will Always Love You"

Jive

For most of its run, A Tribe Called Quest's 1991 masterpiece The Low End Theory is refined and restrained, all tasteful jazz thump and sophisticated introspection. But for its closing barrage, Q-Tip and Phife cut loose with the New York crew Leaders of the New School on an absolute lung-buster that anticipated the shouty, mic-grabbing styles of Das EFX and Wu-Tang Clan. The energy was undeniable, as was the star-making turn from Busta Rhymes, whose verse doubled as a mission statement for the track, if not his entire being: "Causing rambunction throughout the sphere/Raise the levels of the boom inside your ear." –Evan Rytlewski

Listen: A Tribe Called Quest, "Scenario"

Shimmy Disc

Daniel Johnston recorded the spare piano ballad "Some Things Last a Long Time" during a 1988 visit to New York City. After he stopped taking his medication, the trip spiraled into a manic episode. In the span of a few days, Johnston was arrested for vandalizing the Statue of Liberty, assaulted at a homeless shelter, admitted into a psychiatric ward, and then released due to clerical error in time to play a gig at CBGB.

That "Some Things Last a Long Time" exists at all is a testament to the small army that loved Daniel, that lifted him up when his sanity left him. But Johnston alone renders the song a body blow. He delivers lyrics as simple as nursery rhymes with the somber regret of a deathbed confession. Covers abound, by artists including Lana Del Rey, Beck, and Beach House, but none will last as long, or hurt so much, as Johnston conveying his grief into eternity. –Peyton Thomas

Listen: Daniel Johnston, "Some Things Last a Long Time"

Kedar / Universal

Baduizm's first single is quintessential literature in the Badu canon, and the neo-soul movement at large. Rarely was she the easiest narrator to interpret, but for as alluringly coded as "On & On" is, there's a clear political undercurrent girding the track. "My money's gone/I’m all alone" her sultry alto voice crooned over a slick four-note bassline, the first of many existential declarations—an opening address for a new generation of earth mothers, Afrofuturists, and doobie burners to follow like scripture. Despite—or because of—its elusiveness, the song has become one of the great chilled-out anthems for Black folks building new worlds in a country working hard on their demise. –Gio Santiago

Listen: Erykah Badu, "On & On"

Maverick / Warner Bros.

A culture-shaping fusion of UK acid house and American dance pop that still betrays its origins as a bluesy travelers’ lament (doesn't the Zephyr sound like a train?), "Ray of Light" is, simply, a song about flying. The title track of Madonna's first mystic reinvention started out as a heavy-hearted folk tune recorded by British duo Curtiss Maldoon in 1971; the version she created with electronic producer William Orbit is raving psychedelic pop disco, full of laser arpeggios and sirens that move with the silvery magnetism of ocean fish. A Kabbalah-coded ode to divine femininity with a racing pulse, "Ray of Light" is body music for the embodied consciousness. –Anna Gaca

Listen: Madonna, "Ray of Light"

LaFace / Arista

Anchoring their classic 1994 album CrazySexyCool, "Creep" is TLC's mischievous justification for revenge cheating on a partner who's abandoned any sense of trust. Smooth, decisive, and almost numb in her delivery, T-Boz sells the feeling of emotional detachment with her signature deep rasp, relaying a message that sometimes the most cathartic response to a messy relationship is to get even messier. Today's R&B is so rich with women doing dirt that it's almost quaint to remember an era when a song about a woman cheating as emotional retribution was an aberration. It's a feat that she waited until the 22nd of loneliness to do so. –Clover Hope

Listen: TLC, "Creep"

Virgin

While Frankie Knuckles’ pioneering early tracks were soaked in acid and eroticism, his sound became warmer and more soulful as the genre of "house" solidified. The title of his 1991 album Beyond the Mix captured the essence of deep house: Beyond the music and the musician is the potential for collective experience that dance unlocks, the ego death and emergent sense of togetherness that can come from existing as one unit within the unified organism of a crowd. While elsewhere Knuckles works with vocalists to deliver fervent club Jeremiads over an electronic chorus, "The Whistle Song" is pure sound. There's no direct address or thematic telegraph, and in its simplicity, Knuckles’ instrumental opus demonstrates the possibility of dance music as pure feeling, unbound from time and language. The titular whistle is our guiding compass in a misty soundscape that dissolves the barrier between musical rhythm and natural ambience. –Nadine Smith

Listen: Frankie Knuckles, "The Whistle Song"

Cash Money / Universal

Not only is "Back That Azz Up" the defining hit of Cash Money, its opening strings are still an alarm call to clear out of the dancefloor if you’re not ready to sweat. There's Mannie Fresh's propulsive, funky beat; Juvenile's direct command to throw ass; the hypnotic flow in his verses have the effect of bounce music; the jolt of adrenaline every time the hook comes back around. It's all sort of romantic, too, how Juvenile treats a little ass shaking like the blessing that it is. In the future, Cash Money would reach higher commercial peaks, but not much lives on like a twerk anthem. –Alphonse Pierre

Listen: Juvenile, "Back That Azz Up" [ft. Mannie Fresh and Lil Wayne]

Mr. Lady

When "Deceptacon" came out in 1999, the idea of an indie band being both pop-positive and confrontationally political wasn't as familiar as it is now. Like the early rock’n’roll it quoted, the song was, in essence, dance music—a quality foregrounded by James Murphy and Tim Goldsworthy's remix a few years later. And not just dance music, but the kind of immediate, floor-filling shout-along that glossy regional magazines were recommending as bridal-party entrance music. That riot grrrl pioneer Kathleen Hanna, who’d quit Bikini Kill a few years earlier, wrote the song out of frustration with watching feminism's dilution through stuff like the Spice Girls and Xena: Warrior Princess made sense: This is cute, fun music in part about the cultural complexity of young women having cute fun. –Mike Powell

Listen: Le Tigre, "Deceptacon"

Virgin

Janet Jackson is staring down an oblivious dude from across the room while thinking some very naughty thoughts. "If you like I’ll go down, da-down, down, down, da-down, down," she mumbles in a hypnotic monotone, before opening up her voice to underline the innuendo, "Your smooth and shiny feels so good against my lips, sugar." "If," the fiercest track from her chart-obliterating janet. album, clears a path for her freakiest fantasies. The production, by Janet and her longtime collaborators Jimmy Jam and Terry Lewis, is a genre-defying riot—feral guitars that bring to mind prog rocker Robert Fripp smashed together with an artfully flipped Supremes sample and steel-hard hip-hop drums inspired by Public Enemy. Urged on by the turbocharged beat—and a dance-heavy video where Janet memorably pushes a guy's head toward her crotch—this horny hypothetical of a song is fully realized. –Ryan Dombal

Listen: Janet Jackson, "If"

Columbia

From the moment "Always Be My Baby" begins, it's immersed in nostalgia. What sounds initially like an acoustic guitar has the artificial shimmer of a romanticized memory, while Carey's wordless chorus feels Motown-esque, buoyant in the face of what should be heartache. But "Always Be My Baby" is not a breakup song. It's a song about eternity. Just because something is over doesn't mean it's over; every touch is in some way permanent, and anyone who passes through your heart leaves their shape behind. This infinite wave pool of romantic longing was a point of transformation for Carey—her first collaboration with Jermaine Dupri, who helped push her sound further into the gleam of hip-hop. "Always Be My Baby" is, by contrast, in no hurry to get anywhere, certain that even as things change they also recur, making for a cozy, classical R&B song that's also a portal between worlds, flowing into and out of them forever. –Brad Nelson

Listen: Mariah Carey, "Always Be My Baby"

Pendulum / Elektra

"Rebirth of Slick" captures Digable Planets’ preternatural chemistry and indelible cool. From the slowed sample of Art Blakey & the Jazz Messengers’ "Stretching" to the buttery rhymes and neat drums, the song exudes a carefree spirit that's indebted to the Native Tongues but spacier and more inquisitive. The smoothness of jazz rap sometimes veers into corny respectability, but the mood here is loose and playful, the Planets referencing childhood hairstyles, movies, and outfits. Even as the verses showcase everyone's individual styles, the constant mentions of "we"and "us," along with the mic-passing riffs that close the song, channel the group's history of sharing meals together and recording in a closet studio, their cool generated not just by the obscure jazz they all adored, but by their connections to each other. –Stephen Kearse

Listen: Digable Planets, "Rebirth of Slick (Cool Like Dat)"

Elektra

You can't craft a song like "Groove Is In the Heart" without a good ear for timing, a strong sense of camp, and the stamina for digging deep into the crates—all qualities that Deee-Lite's DJ Dimitry and Lady Miss Kier honed on the late ’80s NYC club scene. Parliament-Funkadelic's Bootsy Collins, legendary sax player Maceo Parker, and a young Q-Tip guest on "Groove Is In the Heart," while many more are represented through snippets of sound: the slide whistle and crowd noise from soul singer Vernon Burch's "Get Up," Eva Gabor saying "I" on loop from the Green Acres theme in the chorus, a drum loop nicked from Billy Preston to cradle Tip's rap, and that Herbie Hancock bassline. Without the snap, crackle, and pop of such tactile details, the genre-defying dance hit might not sound so much like a party you never want to leave, where they give out tabs of acid along with a toy noisemaker. In a decade filled with ’70s revivalism, house-inspired pop, hip-hop's creeping influence, and countless weird one-hit-wonders, Deee-Lite were one of the few good acts at the center of the Venn diagram. –Jill Mapes

Listen: Deee-Lite, "Groove Is in the Heart"

FFRR

Named after a tranquilizer that Orbital members Paul and Phil Hartnoll witnessed their mother taking during their childhood, the original "Halcyon" unfolds like a drug trip itself, a universe of motion blurs (some of which are reversed echoes of Kirsty Hawkshaw's vocal from Opus III's "It's a Fine Day") with percussion moving restlessly beneath it like insect legs. The track is far more recognizable in its remixed form, however, due to its placement on the soundtracks for ’90s blockbusters like Hackers and Mortal Kombat. With the subsequent rise of sampling, the remixed "Halcyon"—titled "Halcyon + On + On"—is in many ways emblematic of a decade where music increasingly sounded like a written-over palimpsest. The beat is straightened out, a piano shimmers in the distance like a desert mirage, and Hawkshaw's voice sweeps like winds over a landscape of pulsing ambient techno. –Brad Nelson

Listen: Orbital, "Halcyon + On + On"

Death Row / Interscope

When cable news came of age in the ’90s, L.A.'s public image swiftly became collateral damage. A regional ode for the ages was never more badly needed than in 1995, when the city was firmly under the microscope of a national media eager for more footage of riots or the next Bronco chase. So two of Death Row Records’ greatest creative minds willed one into existence. On "California Love," Dr. Dre goes into full hitmaker mode by refurbishing familiar pieces of musical history, including a Joe Cocker riff and a Ronnie Hudson refrain, into pure party-anthem bliss. With the special sauce of vintage talkbox vocals from Zapp's Roger Troutman, Dre and a freshly inspired 2Pac repossessed and momentarily redirected the nation's attention toward a sunnier view of California. –Steven Arroyo

Listen: 2Pac, "California Love" [ft. Dr. Dre and Roger Troutman]

Cooltempo

"Brown Sugar" is effortlessly cool: In the music video, D’Angelo struts into a dimly lit lounge, sits at the piano, and instantly busts out the sweetest serenade, with smoke from a joint still coming out of his mouth. If you told me that's how he actually recorded the song, I would absolutely believe it.

In an era when much of the popular R&B singles had been inspired by Teddy Riley's new jack swing slickness, D’Angelo's debut hit was a slow-burner that felt beamed in from another universe. Inspired by icons like Marvin Gaye, Al Green, and Stevie Wonder, the Virginia-raised singer pulled from those retro roots while addings elements of hip-hop, helping to lay the foundation for neo-soul. The rap influence is in D’Angelo's look—cornrows and baggy clothes—but also in the tinny drums programmed by A Tribe Called Quest's Ali Shaheed Muhammad, which give the song an almost slow-mo bounce. Filtered through the singer's honey-smooth falsetto and mystic allure, the past and present become seamlessly intertwined. –Alphonse Pierre

Listen: D’Angelo, "Brown Sugar"

Island

The Cranberries’ "Dreams" is the sensation of butterflies in your stomach incarnate: "Oh, my life is changing everyday/In every possible way," Dolores O’Riordan sings, capturing the terrifying thrill of entrusting your heart to someone who could shred it to pieces, or make your wildest fantasies come true. With an arrangement that seems to say "go after your heart's desire, but be careful!," "Dreams" gallops forward atop sweeping guitar chords and quietly rumbling drums, only to consistently rein itself in. O’Riordan begins each verse from a place of softness, as if she's floated back to Earth and needs to touch some grass to reassure herself that this is real. But ultimately, the euphoria is too big for words: O’Riordan emits a fierce yodel, opening her throat to the sky and letting those fluttering feelings pour out. –Quinn Moreland

Listen: The Cranberries, "Dreams"

Epic

If there's one song that harnesses Sade's capacity for aquatic melancholy, it's "No Ordinary Love." This isn't only because of the music video's marine setting, which depicts lead singer Sade Adu as a brooding mermaid who aspires to be a human bride. There are the chugging guitars in the chorus, which crest like the peak of ocean waves; the fluid fog of synths that floats over sparse percussion; and of course, the unrelenting devotion central to the lyrics, which become liquid velvet between Adu's lips. The oceanic aura that surrounds "No Ordinary Love" might be mellow, but it's also one of the UK band's most piercing and desolate moments. After all, that's what love feels like when it's elusive, especially after you’ve emptied yourself in service of another: as isolating and bottomless as the sea itself. –Isabelia Herrera

Listen: Sade, "No Ordinary Love"

Rap-A-Lot / Priority

Among the most haunting street-life narratives ever recorded, this masterpiece by Houston's Geto Boys rewired hip-hop's supposed binaries—between East Coast and West, conscious poets and amoral journalists—unpacking drug game paranoia over a plaintive loop of Isaac Hayes’ "Hung Up on My Baby." The ghostly, pitched-down guitar figure sets up some ironic distance from the grim narration while also telegraphing cartoon violence by way of the Blaxploitation classic Three Tough Guys, which starred Hayes and featured his song on its soundtrack. Reprising the candles-in-a-dark-room scenario from the band's horrorcore salvo "Mind of a Lunatic," Scarface goes deep, evoking Jim Crow nightmares and a present-day vision of himself "sleeping with my finger on the trigger," as well as contemplating suicide as an escape, rejecting it on his son's account, and lamenting the love he lost through his callousness. The song became an emo-rap touchstone, referenced by artists from Biggie to OutKast to Kid Cudi, who credited it with inspiring his breakout "Day ’n’ Nite" and called it "his favorite song in the world." –Will Hermes

Listen: Geto Boys, "Mind Playing Tricks on Me"

Matador

Pavement started as a scuzzy noise-rock project, but elegance turned out to be their secret weapon. Yes, Stephen Malkmus used the word to mock Stone Temple Pilots in "Range Life" but it was the pot calling the kettle black—from his baseline game to his perfect haircut to his endlessly inventive guitar fills, Malkmus radiates the stuff, and Courtney Love was dead on when she called him the Grace Kelly of rock. "Gold Soundz" was merely one brilliant single among the many the band released across the decade, but it was the first one to show the world just how refined they could be. Every element—achingly nostalgic lyrics, jangly chord progression, succinct guitar solo with a perfectly graceful tone—is arranged just so, not a note or a word out of place. –Mark Richardson

Listen: Pavement, "Gold Soundz"

Uptown / MCA

Between its main radio edit and its various 12" remixes, Mary J. Blige's "Real Love" came with several different introductions: If the tune's "Top Billin’" drumbeats didn't grab you, maybe starting with the guitar riff from "Clean Up Woman" or Mary's jazzy a cappella ad-libs would. Her raw gift for impromptu gospel and jazz singing paralleled the improvisational impulses of rising MCs and hip-hop DJs; so when Biggie Smalls added a few bars to the remix, you heard his rhymes juxtaposed against isolated melodic phrases that revealed structural similarities in Blige's delivery. In an era when danceable rap records were increasingly crossing from Black radio to "pop" stations, "Real Love" wed roller-disco tempos to B-girl vulnerability. The combination of kinetic rhythms and passionate, confessional vocalizing became the signature sound for the emergent Queen of Hip-Hop Soul. –Carol Cooper

Listen: Mary J. Blige, "Real Love"

Epic

Fiona Apple was in the middle of recording her 1996 debut album Tidal, and she was miserable. Spotting a white dove in the sky, she took it as a sign that everything was going to be okay. Looking closer, she saw that it wasn't actually a bird at all—it was an airborne plastic bag. She was crushed. Apple turned this sense of disappointment into "Paper Bag" on her magnificent 1999 album When the Pawn… She expresses frustration with a romantic partner she dismisses as a "little boy," while recognizing that she's a lot to sign up for ("I know I’m a mess he don't wanna clean up"). The hint of swagger in the beat and the gorgeous Beatles-y horns in the coda reflect this nuanced mix of melancholy and defiance. "I’m a fucking contradicting little kid most of the time," Apple said in a 2000 interview, "except in my songs. That's the only time I can actually focus and go, ‘This is the truth about this. This is the way it is.’" –Alan Light

Listen: Fiona Apple, "Paper Bag"

Roulé / Virgin / Because

The promise anchoring French house is that one perfect loop can change your life. When producer Alan Braxe, singer Benjamin Diamond, and Daft Punk's Thomas Bangalter came together as Stardust and clipped a few seconds from Chaka Khan's "Fate," they rocketed into the annals of dance music history. "Music Sounds Better With You," the trio's lone single, is meant to be shared with other people, emphasizing communal ecstasy in the way Diamond sings "with you!" like it's lifting him an inch off the ground. The song's generous bliss laid the groundwork for Daft Punk's shift from the DJ tools of Homework to Discovery's accessible craftsmanship, and decades later its basic principle—a tight, filtered nibble of joy—is part of pop music's lingua franca. –Jamieson Cox

Listen: Stardust, "Music Sounds Better With You"

Blackground / Atlantic

Skittering percussion and squirming sub-bass have dominated rap and pop production for so long now it's easy to forget that when Aaliyah's "One in a Million’’ debuted in 1996, Timbaland's style had yet to gain a foothold on radio or MTV. Just four seconds into the song you hear it, though: the rapid flicker of hi-hats, the element that always made his early work sound as if it were a stuttering transmission from the future. Every time it happens in "One in a Million" it's like time mutates, lurching forward and then snapping back on itself like a rubbery cartoon character. In this case it mirrors the song's subject: falling in love with someone so hard that you feel the continual pull of their gravity. And no voice navigated these thickets of drum patterns more capably than Aaliyah's; she rides the currents of the undulating groove as if she were piloting a hang glider through them. –Brad Nelson

Listen: Aaliyah, "One in a Million"

Ruffhouse / Columbia

Like any great breakup song, "Ex-Factor" has its own mythology: It was reportedly written about Lauryn Hill's affair with Wyclef Jean, her former Fugees bandmate. But does that even matter? It's a plea that will serve as a balm for anyone and everyone as long as hearts are getting broken. Featuring one of Hill's all-time great vocal performances, the song's genesis alone spans generations and genres: The unsettlingly plaintive opening line is adapted from a Wu-Tang Clan sample of a Gladys Knight & the Pips’ cover of Barbra Streisand's "The Way We Were"; Hill's track, in turn, has been sampled countless times since. And with its encouraging ad-libs, it almost sounds like a private duet with and to herself, a reminder in the margins that she—just 23 when she wrote it, yet possessing razor-sharp emotional clarity—deserves better. –Emma Carmichael

Listen: Lauryn Hill, "Ex-Factor"

LaFace / Arista

If "SpottieOttieDopaliscious" sounds like a fantasy of a night out at the club, that's because it is. Andre 3000 wrote his verse about a night he almost went to Charles’ Disco as a teenager, but found himself too drunk to walk in the door—"So all the stuff I said after that," he told an interviewer later, "was made up." The production has the wooziness of a dream or a memory half recollected from inebriation: humid wah-wah guitar, a reggae-ish rhythm section that ambles along with no particular place to be. And then there's the horn line, one of the greatest instrumental hooks in pop history, stretching out across eight full bars, both languid and triumphant. Andre and Big Boi deliver their verses like they’re talking to you from across the pool table, more spoken word than rap. In the former's, revelry erupts suddenly into violence, possibly fatal; in the latter's, the decision to grind up against a stranger leads eventually to unexpected fatherhood. The club becomes a kind of crucible, not just a venue for drinking and dancing, but a place where the twin possibilities of death and new life lurk in the background of every scene. —Andy Cush

Listen: OutKast, "SpottieOttieDopaliscious"

Maverick / Reprise

In 1995, a 21-year-old Alanis Morissette shunned the bubbly sound that had made her a pop star in Canada and released the incendiary kiss-off "You Oughta Know." Long before Taylor Swift and Olivia Rodrigo angrily called out their exes in song, Morissette explored the rage she felt when her partner unceremoniously tossed her aside. If she didn't get to escape her feelings, neither would he.

Moving from a fugue-like calm to detailed accusations over a roving bass line and refracted guitar, Morissette built catharsis out of her pricklier emotions and helped usher in an era of women songwriters who fervently hungered to be themselves. The song dropped like a lit match on parched earth, becoming the first of three hit singles from her breakout album, Jagged Little Pill. Morissette's fury became a wildfire, and listeners heard themselves in the burn. –Amanda Wicks

Listen: Alanis Morissette, "You Oughta Know"

LaFace / Arista

"No Scrubs" is a cold-hearted diss, but it's also a song about putting your foot down and finally valuing your self-worth. It would be mean if it wasn't so funny, especially when they nail the specifics on the bridge: Guys that don't have a car should keep it stepping, and if your mom is your roommate don't even try to waste their time. Most of all, it sounds beautiful: Chili's strong and sweet lead vocals, the angelic background harmonies, the futuristic flourishes of the instrumental, Left Eye's robotic raps preserved in arguably the definitive Hype Williams music video. It remains the holy grail of deadbeat boyfriend ethers, a sentiment frequently captured but not with the balance of theatrics and truth that TLC had down pat. –Alphonse Pierre

Listen: TLC, "No Scrubs"

Nothing / TVT / Interscope / Atlantic

Hissing "I want to fuck you like an animal" was shocking enough to become a sexily confrontational mantra or a sign of societal decay, depending on who was doing the listening. The second single from The Downward Spiral launched Trent Reznor and Nine Inch Nails into a new tier of notoriety, a couple of years after Pretty Hate Machine had established him as the aggro prince of industrial rock. Singing from the raw and dangerous perspective of a self-hating obsessive, set to bone-rattling beats that sounded like they were recorded in some grimy sex dungeon, Reznor sounded like he was both tortured and doing the torturing. It was accentuated by a hardcore music video stocked with unsettling imagery like Reznor done up in S&M gear and a very anxious monkey tied to a cross. Still Nine Inch Nails’ most popular song, an enduring strip club anthem for three decades, and a weird one to do at karaoke, "Closer" is the sound of self-loathing as a twisted kind of love letter. –Evie Nagy

Listen: Nine Inch Nails, "Closer"

Atlantic

Brandy laid down her feathery sweet vocals in California, while Monica recorded her tough and soulful melodies in Atlanta. Some have said it's because their voices weren't meshing; others have said it's because they couldn't stand each other. That they’ve only sung the soap opera-ready R&B classic once together live—on that same night Monica punched Brandy in the face—is reason enough to go with the latter. "The Boy Is Mine" has a simple driving idea: Brandy and Monica have found out that they are dating the same man. It's fiction, but as they trade stingy jabs, that line between reality and story is blurred, and the way Brandy airily coos "He said without me, he couldn't make it" probably hurts more than any punch could. Rodney Jerkins’ beat is the perfect backdrop, a harp buildup that could heighten any melodrama and a shimmering and shaking feel that gives the song more edge than it already has. Neither Brandy or Monica outshine each other, as their voices line up like two puzzle pieces. It's one of the great duets of our time, even if they couldn't stand each other. –Alphonse Pierre

Listen: Brandy / Monica, "The Boy Is Mine"

Circa / Virgin

"Teardrop," the centerpiece of Massive Attack's Mezzanine, is themed around water and feels made of it—to this day, downtempo artists are still searching for its depths. The instrumental is narcotic but simple: two bars of harpsichord that vary by one note, sustained piano chords, percussion ticking like a hypnotist's pendulum. Guest vocalist Elizabeth Fraser's voice moves like liquid, too, high notes evaporating and melisma cascading like a waterfall. She realized only after recording that she’d written the lyrics for former partner Jeff Buckley, who died when she was recording the song. Those lyrics are a series of oblique what-ifs, meditations on the ideal love she never achieved. She sings her regrets into the waiting abyss. –Katherine St. Asaph

Listen: Massive Attack, "Teardrop"

Jive

Britney Spears is so thoroughly woven into our cultural fabric—her rise, fall, revival, restriction, and liberation—that you forget she once needed to introduce herself. Her origin story is the stuff of legend: A driven Louisiana teenager met an enigmatic Swede who had written hits for the Backstreet Boys and Robyn. She flew to Stockholm and purposefully stayed up too late the night before recording her vocals, making her voice, as she once put it, "rusty." Then Spears and Max Martin entered the studio and reshaped the next quarter-century of pop music, like a dam redirecting a river's flow.

"...Baby One More Time" is the dam, a structure crackling with energy. Like so many great pop songs, it taunts the listener by conflating the romantic and the religious: confession, belief, begging for a sign. The spiritual desperation, alongside Martin's precise melodic techniques, is what makes a high school crush feel like life or death. Would-be stars and ambitious producers have been chasing that transgressive thrill for decades, but it's tough to top the original sin. –Jamieson Cox

Listen: Britney Spears, "...Baby One More Time"

Death Row / Interscope

Rappers don't ask for permission when they’re about to fundamentally change the course of pop culture. N.W.A. certainly didn't with Straight Outta Compton, and yet Snoop Doggy Dogg and Dr. Dre began "Nuthin’ But a ‘G’ Thang" ready to make an entrance and politely requesting that you give them a little space before they freed hip-hop from two decades of tyrannical East Coast rule. Over the most luxurious production ever heard on a rap record to that point, the duo trade lines like they’re just hanging by the grill at a neighborhood cookout; no human being has ever sounded cooler simply spelling his own name. But by the first chorus, Snoop and Dre assume you’re down enough to understand what this and that are like, and if not… just chill to the next episode, because there will be plenty more. Snoop and Dre no longer have to ask us to let us in our homes; it's been thirty years since "Nuthin But a ‘G’ Thang" and they’ve never left. –Ian Cohen

Listen: Dr. Dre, "Nuthin’ But a ‘G’ Thang" [ft. Snoop Dogg]

550 / Epic

"Pony" has got all the makings of a classic, sure: It's one of Timbaland's first major hits, its croaking vocoded "yea, yea, hell yea" beat is immediately recognizable at the club, and there are even ready-made dance cues. But there's so much more. It can be a reach to project yourself into the panty-dropper protagonist of a sexy club anthem, but Ginuwine's unbridled commitment to the bit (saddles! jockeys! ponytails!) has an earnestness to it, empowering even the least likely cowboy to jump on it. "Pony" is both the soundtrack to Channing Tatum's Magic Mike dancing at his absolute peak, and a down and out Magic Mike cracking a smile and dancing alone in his wood workshop. After all, beyond the bit, "Pony" earns its enduring reign by being a genuinely fun and hot track to grind to—whether in the club or by yourself. –NM Mashurov

Listen: Ginuwine, "Pony"

Jive

By the time he was 16, Q-Tip had produced much of what would become People's Instinctive Travels and the Paths of Rhythm, the debut album that would earn him and his partners in A Tribe Called Quest the first 5-mic rating from ’90s rap bible The Source. The process was painstaking—he spent hours isolating samples on pause tapes, drawing from his father's extensive record collection—but the beats it yielded were loose, uncluttered, inevitable. "Can I Kick It?" turns the bassline from Lou Reed's "Walk on the Wild Side" into a looping shrug, which in turn allows him and Phife Dawg to dial the early Native Tongues ethos down from sunny but quasi-militant to bemused. The call-and-response hook reveals the group as adolescent observers of hip-hop's first decade, but would itself be riffed on by innumerable rappers to come. –Paul A. Thompson

Listen: A Tribe Called Quest, "Can I Kick It?"

Parlophone / Capitol

"Paranoid Android" belongs to the class of epic rock songs that overexert themselves again and again, fully aware of their own absurdity: Queen's "Bohemian Rhapsody," The Beatles’ "A Day in the Life," David Bowie's "Space Oddity." Recorded in the mansion of a former James Bond girl and pared down from a 14-minute original version, Radiohead's through-composed theatrical extravaganza changes keys repeatedly, whips out multiple guitar solos, and brings in a choral arrangement while waxing about governmental control. It's beyond indulgent, a perfect entry into the category of songs that inspire you to sing along like you’re Wayne and Garth. –Nina Corcoran

Listen: Radiohead, "Paranoid Android"

Warner Bros.

"Believe" marked a new era, for Cher and for popular music. For the first time on Top 40 radio, Auto-Tune—producers’ open-secret weapon for perfecting vocal takes—was laid bare for all to hear, on purpose, a reversal of its typical clandestine use. As she sings about trying to regain her footing after heartbreak, Cher's voice warbles with synthetic oscillation. Warner executives initially scoffed at the effect, but "Believe" became one of Cher's biggest career hits, reaching No. 1 in the United States and more than a dozen other countries. Just as the song's production revealed the guts of its operation, Cher's wide-open vocals exposed her own emotional vulnerability. She isn't too good to admit she's not hurting, and she powers through toward salvation, declaring "I don't need you anymore" as the song hits its peak. And coming from Cher—a confident, charismatic, and massively talented woman who’d been subjected to frequent public ridicule over her personal life—"Believe" took on an extra survivalist edge. Nearly 25 years later, it still dazzles in its defiance. –Allison Hussey

Listen: Cher, "Believe"

4AD / Elektra

When this song cracked the Top 50 in 1993, it made obvious what was always true: Kim Deal, heretofore regarded as a slacker from Dayton, Ohio who played the bass for the Pixies, can write explosive pop songs. On "Cannonball," the bass is front and center; loud, noisy, mean. Over top of that squall, she cackles into the mic with the bravado and control of a punk rock Mozart. She sings about bongs and goes sadomasochist mode by implying that she's a little bit of a libertine. It's sexy, it rocks, and it makes you want to light a car on fire (with your lover). –Sophie Kemp

Listen: The Breeders, "Cannonball"

Grand Royal

As Beastie Boys tracked Ill Communication, MCA, Mike D, and Ad-Rock became a scourge to their engineer and co-producer. The tormented Mario Caldato Jr. begged the band to finish the album—to finish a song, for fuck's sake—and occasionally succumbed to tantrums that involved chucking equipment out of the studio window. "Sabotage," Beasties’ pummeling, era-defining return to heaviness, was aimed at Caldato (mostly in jest). The trio is at its most indignant on "Sabotage," with Ad-Rock in particular shrieking like a punk rock Joe Pesci. It may have been a harbinger of much-maligned late ’90s rap-rock—Limp Bizkit, Linkin Park, and Papa Roach all released debut LPs in the ensuing years—but "Sabotage" was also an undeniable triumph in the band's own legacy. The song's wheezy, robotic scratching foreshadowed the hyper-digital funk of "Intergalactic," while its modest structure and blaring guitar signaled a return to form. After years of crafting sample-jammed hip-hop, Beastie Boys could still kick the door in, blow out your speakers, and piss off your parents. –Madison Bloom

Listen: Beastie Boys, "Sabotage"

Junior's Own Boy / Wax Trax! / TVT

The lyrics are an alcoholic cry for help, and much of the song plays out to the isolated thud of a kick drum. Yet "Born Slippy (Nuxx)," a non-album single from improv-heavy UK electronic outfit Underworld, became a sacred text for ravers in the ’90s, not to mention a musical lynchpin to Trainspotting, one of the decade's most revered movies. These kinds of contradictions are ingrained in the wide-screen techno masterpiece, which combines the most perfectly uplifting three-note keyboard riff with descent-into-hell drums, and stream-of-consciousness verses with a two-word refrain that became shout-along iconic. "Born Slippy (Nuxx)" was one of the most extreme hit songs of what was a pretty weird decade for music, a tone poem of confusion and distress that soundtracked some of the ’90s’ happiest memories, and a reminder that sometimes even the most outlandish electronic producers can stumble across pop gold. –Ben Cardew

Listen: Underworld, "Born Slippy (Nuxx)"

Chrysalis

As written by Prince, "Nothing Compares 2 U" was already a heartbreak anthem for the ages. The lyrics incorporate enough specifics to conjure the obsessive banalities of a breakup ("It's been seven hours and 15 days…") and enough sweeping generalities to express its primal significance. The sparse arrangement is full of space and catharsis, and the chorus melody manages incredible catchiness while also mimicking the fragmented speech of a sobbing breakdown.

But nobody could sing it like Sinéad O’Connor, who, in her early 20s, seemed to understand a more existential question at the song's core. Consider the way she lingers in the unresolved final note of the chorus, twisting and holding the word "you" as if beckoning it from somewhere dark and far away. Or what about the way she changes one line to address a male object of affection but specifically leaves in a very Princian utterance of "mama" during the final verse? It's around this moment in the music video—a close-up of her face that would define O’Connor's mainstream image and help sweep the song to No. 1—that her eyes begin welling with tears, and you start wondering if she really is just singing about a breakup, or something else.

In retrospect, O’Connor has explained the tears were unplanned, brought on by thoughts of her mother, an abusive figure who tormented the Irish singer throughout her childhood and died in a car accident just before her career took off. Their relationship was complicated, and the song—whose last verse ends with an unanswered plea to "give it another try"—closes without much of a glimmer of hope. There could be no better introduction to O’Connor's raw talent: a poet of conflicted emotions, using her voice to express feelings that exist between and beyond words. –Sam Sodomsky

Listen: Sinéad O’Connor, "Nothing Compares 2 U"

Island

Formed in 1978 by a couple of Sheffield teens, Pulp slogged through lineup and label shifts without commercial success—until the Britpop explosion of the mid-’90s provided a new world stage for their fifth album Different Class and its career-defining lead single. A much sexier, stirring, and more appropriately cynical UK counterpart to "Uptown Girl," "Common People" was the story of ceaselessly magnetic frontman Jarvis Cocker's art school dabbling with a rich girl who was excited by the idea of slumming it with poor folks like himself. He humored her—and was happy to sleep with her—but the song was a harsh criticism of class tourism by people who would never know poverty, a populist anthem built for hours of sweaty dancing regardless of socio-economic status. –Evie Nagy

Listen: Pulp, "Common People"

Go! Discs / London

Portishead are masters of digital psychedelia, of artificially eroded samples and breaks that encase fiery yearning in soothing layers of ice. Situated in the unbridgeable gap between fantasy and fate, the Bristol trio endures as a monument to our own sublimated desires. "Sour Times" spins this existential despair into a fatalistic noir dreamscape. Vocalist Beth Gibbons tosses and turns over a sinuous bassline and guitarist Adrian Utley's best Morricone riffing, bathing in the cursed knowledge of a lost love's inescapable power. The song draws its hypnotic majesty from the thrill of Gibbons’ graceful rage, poised between succumbing to an eternity of longing and spitting venom in destiny's eye. It's a haunted waltz for star-crossed androids, damned to soundtrack disconnected hearts far beyond the singularity. –Phillipe Roberts

Listen: Portishead, "Sour Times"

Columbia

George Michael's subdued and pensive sophomore solo album Listen Without Prejudice, Vol. 1 showed a different side of the frequently bubblegummy superstar, and "Freedom! ’90" laid bare its mission statement: Sometimes the clothes do not make the man. Perhaps to the chagrin of every hungry schoolgirl, the star's image never graced Prejudice, neither on its cover nor its videos. The music was to speak for itself, and on "Freedom!" it did so using a "Funky Drummer" break and Madchester-y piano riff. The song's strut mounts until an ebullient choir detonates, repeatedly harmonizing the song's title. That freedom was to be achieved, in Michael's estimation, via image revision: "There's something deep inside of me/There's someone else I’ve got to be." Attempting to conjure authenticity in show business is about as easy as declaring yourself vegan while only eating at steakhouses, but "Freedom!" is about concept, not practice, suggesting the journey to happiness rather than the destination. For the classic video, Michael enlisted a slate of high-profile lip-syncers—Naomi Campbell, Cindy Crawford, Christy Turlington, Linda Evangelista—who helped provide beautiful scenery on his quest. –Rich Juzwiak

Listen: George Michael, "Freedom! ’90"

Loud / RCA

"Shook Ones, Pt. II" is so rich a text that isolated elements of it communicate more style and biographical depth than nearly any other introduction in hip-hop's history. There's the Herbie Hancock piano that Havoc morphed, in his mother's apartment, into one of rap's most unmistakable basslines; there's Prodigy's opening ad-lib—"To all the killers and the hundred-dollar billers/For real niggas who ain't got no feelings"—and what it suggests is being elided in his verses; there are those hi-hats, which people believed for years to be the sound of stoves in the Queensbridge Houses sputtering to life. Even the mesmerizing siren loop tells a story: It's lifted from a song by Quincy Jones, whom Prodigy's grandfather taught to read music. And still, all of this becomes secondary when P raps—about the burn of bullets in flesh, about hoping to die in a place like Queensbridge, and about how, if you don't watch yourself, "the next rhyme I write might be about you." –Paul A. Thompson

Listen: Mobb Deep, "Shook Ones, Pt. II"

Epic

"I’ve been a bad, bad girl," Fiona Apple purrs like a vixen in an old man's sex dream, knowing that at 18, a woman is young enough to get preyed on and old enough to get pilloried. "Criminal" is her most popular song, potent like a spiked drink, selling a leering public a sexual fantasy while pointing out the fucked-up dynamics underneath. A piano trembles as if announcing the sudden onset of an earthquake, and Apple confesses to the sin of being "careless with a delicate man," her voice dripping with irony. Men are so tough until it's time to take responsibility, then they’re helpless and angry like children. But Fiona howls out for punishment, sounding irresistible while fessing up to her crime. As a new generation of girls likes to say: I support women's rights, but more importantly, I support women's wrongs. –Cat Zhang

Listen: Fiona Apple, "Criminal"

Capitol

A slow waltz beat, a few Dylan chords, a pedal steel like a lamp from an attic window, and Hope Sandoval's downy voice, full of melting vowels and pregnant pauses: "Fade Into You" taps into the sweet exhaustion at the end of it all. Marketed as a make-out anthem off Mazzy Star's major-label debut, it was the mainstream peak for this dream-pop duo that evolved out of psych group Opal, and the platonic ideal of a melancholic slow-dance song. Even as its dusky, enveloping aura echos through Beach House's deliberate dream pop, Taylor Swift's glittering indie folktales, and Faye Webster's weary steel-guitar slides, the ache of the original goes unanswered: The space between us is small yet enormous, the only way forward straight into oblivion. –Anna Gaca

Listen: Mazzy Star, "Fade Into You"

Ruffhouse / Columbia

Lauryn Hill is tender and fierce on her first solo single, offering empathy and stern counsel to women and men in troubled relationships. On Fugees songs she’d often harden her flows (or "add a ‘motherfucker’ so you ignant niggas hear me," as she puts it on "Zealots"), but here and throughout The Miseducation of Lauryn Hill, her rapping is conversational, assured. Motown soul, gospel, and hip-hop converge as she glides over bright horns, crisp drums, and a jingly key riff. She sounds bent on channeling every sound and inspiration she's ever had, harmonizing, scatting, rapping, and humming. The music video features a split-screen motif that pictures her as both modern and retro, but the real takeaway from this song is that she is simply herself. –Stephen Kearse

Listen: Lauryn Hill, "Doo Wop (That Thing)"

Virgin

The music doesn't begin so much as surface, as if "Around the World" arises from some great depth, that lowpass filter cutting out the high-end without obscuring the "fundamental" signal. And then the song fully emerges, the bass suddenly going like something stolen out from under Bernard Edwards’ fingertips, the hi-hat doing that bright, open chhh business on the offbeat. The up-from-underground stuff turns out to have been sort of poignantly appropriate. "Around the World" was an exhumation, disco as reworked in post-industrial Chicago and Detroit, then adapted anew by two blessed weirdos from Montmartre, Thomas Bangalter and Guy-Manuel de Homem-Christo.

Crucially, Daft Punk retained from Chicago house and Detroit techno the artists’ sense that they were bound up in the larger social dynamics of urban de-industrialization. DJs saw themselves as conduits for the music, not its authors. Daft Punk obscured their identities, just as Juan Atkins and Derrick May did before them. They dressed like anonymous robots because, as Homem-Christo has said, "The energy people send to the stage bounces back and everybody has a good time together rather than focusing on us." Disco had returned with a radical proposition, hauled up from the underground without, you might say, affecting the fundamental: that the music belongs to the people dancing to it. –Tommy Craggs

Listen: Daft Punk, "Around the World"

Kill Rock Stars

"Rebel Girl" is a call to arms. Fuck the patriarchy! Ride a motorcycle in a minidress! Fall in love with your best friend—not metaphorically, literally kiss her on the lips! Set alight by snarls of guitars and bass, the song tells us that love is a revelation, an invitation to worship your friends, to see them as beautiful, to shout from the streets that girls matter. That we’re angry. That we’re all geniuses.

By now, "Rebel Girl" has soundtracked personal revolutions across several generations, from Gen Xer chicks on college campuses to Zoomer girls reading Rookie in their high school computer labs. It's so impactful because Kathleen Hanna sang so bluntly about loving so fiercely. And loving someone is one of the punkest things a person can do. –Sophie Kemp

Listen: Bikini Kill, "Rebel Girl"

Bad Boy / Arista

Christopher Wallace's outsized talent as a GOAT-level lyricist is often discussed in terms of his deft wordplay and sophisticated rhyme schemes. From his first hit "Juicy," however, it was also evident how gifted he was as a storyteller. Coalescing all of his prodigious skills over sampled swaths of Mtume's early-’80s R&B smash "Juicy Fruit," the song is ostensibly an autobiographical rags-to-riches tale. But B.I.G.'s attention to detail enables the childhood reminiscences ("Way back, when I had the red and black lumberjack/With the hat to match") and aspirational goals ("Livin’ life without fear/Puttin’ five carats in my baby girl's ear") to transcend individual experience. The song endures largely by being eminently human and relatable—whether, like Wallace, you are or ever were young, doubted, and Black, or if you simply embrace the belief that one's hope for the future, no matter how unlikely, is never merely a dream. –Jeff Mao

Listen: The Notorious B.I.G., "Juicy"

Columbia

Nearly two decades before Beyoncé delivered Lemonade, her heart-wrenching opus on self-transformation and forgiveness in the wake of a partner's infidelity, she led Destiny's Child's glossy, unflinching interrogation of an untrustworthy lover with "Say My Name." Beyoncé's staccato, kinetic delivery—which influenced R&B vocal cadences for years to come—is effortless and unrelenting, underscoring her assertion that she is not one to be played. The song is all bravado, and circles a request so elemental that it shouldn't even have to be asked: to be remembered, and treated with care and respect by someone who loves you. That tension between the audacity of Destiny Child's performance and the vulnerability of their titular ask imbues the song with an incomparable poignancy. –Vrinda Jagota

Listen: Destiny's Child, "Say My Name"

Warp / Sire

With each new development in electronic music, Aphex Twin's "Windowlicker" seems that much more prescient. A decade ago, one heard in it the seeds of later developments in dubstep and the rubbery digital manipulations of the Brainfeeder axis, and 10 years on, it sounds like a foundational text for the broader hyperpop universe. This is what happens when quantum-level auditory science meets plain old musical inspiration.

At the time of its release in 1999, "Windowlicker" was understood as a surprising nod toward pop. Though Richard James’ work was often accessible and he had remixed artists including Jesus Jones and Saint Etienne, nothing he’d done sounded as straightforward and approachable as the opening moments of "Windowlicker." The track's early section, with its eerie warped vocals and hypnotic descending progression, is so indelible you could even imagine hearing it in the wild on the radio. (And so it was in the UK, where the single hit the top 20, powered by the strange and disturbing video by Chris Cunningham.) But embedded within the slippery groove and sighing voices is a feeling that something's a little off, a notion reinforced when it abruptly shifts tempos and descends into blistering noise. James specializes in music that's both beautiful and unsettling, and "Windowlicker" reads like a crackly dispatch from the floor of the uncanny valley, where familiar pleasures are there to be enjoyed but—also never quite what they seem. –Mark Richardson

Listen: Aphex Twin, "Windowlicker"

DGC

As much as anything, it was a breakup song. "Who will be the king and queen of the outcasted teens?" Kurt Cobain asked in a discarded lyric from an early draft of "Smells Like Teen Spirit." One of his biographers is pretty sure he was talking about Tobi Vail, the "over-bored" and "self-assured" riot grrrl vanguardist. The two of them had had a brief romance, which she ended, and Cobain responded in the manner of so many thwarted, sensitive young men, turning rejection into a synecdoche for the oppressions of life writ large. He filled up his journal with violent fantasies and weird drawings. His friends started to worry. And somewhere in this burst of energy, Cobain wrote the perfect pop song.

A denial, a denial, a denial. It hangs over "Teen Spirit" like bad weather. Call it the teenage boy's blues—a young dude's awakening to the fact that he is caught in the crosswinds of, like, the whole system, man, that panders to him, that fires his imagination, and then constrains him, tells him to chill. Very often it's sex being denied. Sometimes it's a car, which is just sex at one remove. Maybe it's money or a fix. Whatever their subject, the teenage boy's blues have been the very stuff of pop music since around the time Chuck Berry went motorvatin’ after that Coupe DeVille. The result has been a great deal of regrettable pop songs, but on occasion there have been transcendent exceptions, like the lead single off of Nirvana's Nevermind. Above all it rips, even still, from that first Gap Band flam to the last, exhausted denial. It's got a screamy part and a soft part, and right at the point where you expect the song to fuzz out and go totally to shit, there's a crisp guitar solo that restates the vocal melody from the verse, almost as if Cobain were satirizing himself and having a damn good time of it.

Well, he probably was, right? Self-doubt is everything in "Teen Spirit." The song famously stands outside itself, mocking its own postures, hating its own apathy and irresolution, anthemic in its insistence on being unanthemic: "Oh well, whatever, never mind." I remember the girls in middle school who had Cobain's photo taped up in their lockers and thinking how funny it was that they were treating this king of the outcasts like something they'd clipped out of Tiger Beat. But of course they were the ones who were actually seeing Cobain clearly—that underneath all the marketing and self-mythology and fraying cardigans there was a true pop idol, beautiful, androgynous, too wounded to be threatening, a troubadour of their uncertainty. He sang as if he were owed something. That's the teenage boy's blues. In the next breath he wondered if he was worthy of any of it. That's a blues for everyone else. –Tommy Craggs

Listen: Nirvana, "Smells Like Teen Spirit"

Goldmind / Elektra

"The Rain" starts with an exhale and a yawn, fitting for a song so playfully trippy it sounds as if it came to Missy and Timbaland in a dream, or maybe after a huge bong hit. Some of the most enduring moments from Supa Dupa Fly—an album that was completed in just two weeks—still sound like studio freestyles, two buddies shooting the shit and making each other giggle in the long spaces between songwriting. The song arrived in the wake of Biggie and Tupac's murders, when hip-hop needed a lift, and it both positioned Missy and Timbaland as industry lodestars and solidified their sound: so tight, as she raps in the song, that you get their styles tangled. Saying "vroom" and "fricky fricky" over that cricket-propelled, Ann Peebles-sampling beat never sounded too silly; it simply sounded correct. –Emma Carmichael

Listen: Missy Elliott, "The Rain (Supa Dupa Fly)"

Matador

"Fuck and Run" begins like an alarm clock, eviscerating Saturday night. A woman wakes up several beds deep in a spree of Sisyphean sex and almost immediately starts to spiral. She sings about fucking and actually calls it "fucking," too. It is impossible to understate how big of a deal this was.

Liz Phair engineered the single to elevate what she called her "awkward morning-after insecurities" to rock airplay, then rock canon. Her guitar work, sometimes criticized as unstudied, is beefed-up, radio-sleek. Her vocal, though flat and casual, is deliberate; she yanks the melody up to show frustration, mumbles out the vulnerable parts. It takes work to sound this unrehearsed. Any potential mopiness is undercut by Phair's goofy humor, like how she backs her forever-alone plaints with jingle bells. And any attempt to make "Fuck and Run" into a big statement on hookup culture is undercut by the whole song being a projection in the woman's head: The guy is just a syllable in her self-fulfilling prophecy; the one running is her. –Katherine St. Asaph

Listen: Liz Phair, "Fuck and Run"

Blackground / Atlantic

"Are You That Somebody?" was the song that consolidated Aaliyah's image as a refined and unapologetic streetwise princess, supplanting the more traditional R&B sound of her work with R. Kelly in favor of something that nudged toward hip-hop soul. The material Timbaland and Missy Elliott created for the singer didn't require her to scream or over-embellish, but rather forced you to listen harder: Aaliyah's vocals grew more compelling the softer and more subtle they became. She could grab attention simply by being unusually calm, the gleaming center of a rhythm track that telegraphed emotional chaos in its fits and starts.

Learning from catastrophic sample lawsuits against De La Soul in 1989 and Biz Markie in 1991, Timbaland became one of the first producers to create signature hip-hop loops out of obscure sound-effect records and found noises. The baby gurgles that punctuate the song's stuttering tango are first ridden by Tim's gravelly vocal affirmations, then by Aaliyah's hushed, reedy croon. The hybridized sound—intentionally odd, jittery tempos, backed by syncopated commentary—was groundbreaking and reflective of something more: the building of a persona around Aaliyah with an even greater mystique than that Jimmy Jam and Terry Lewis had created for Janet Jackson in the years prior. –Carol Cooper

Listen: Aaliyah, "Are You That Somebody?"

One Little Independent

The woman at the center of Björk's "Hyperballad" has a ritual that keeps her alive. She begins each day by sneaking away from her sleeping partner to the edge of the mountaintop she calls home, where she then tosses random detritus down, down, down until they break into pieces. Sometimes, she imagines what her "body would sound like/Slamming against those rocks," curious if she would face her demise with eyes open or shut.

Earth itself seems to awaken as this haunting fable unwinds, from brushed drums that evoke the sound of wind rustling a field to orchestration as slight and sharp as distant crickets. An acid house superbloom of a chorus bursts from this landscape, and the cliffside ritual is revealed as an act of preservation. "I go through all this/Before you wake up/So I can feel happier/To be safe up here with you," Björk sings. It's a track built on polarities: self-obliteration that inspires collective harmony; guttural, thrillingly human vocals set against synthetic sounds; melancholy and exaltation in coexistence. Paving the way for pop cathartics like Robyn, "Hyperballad" imagines a dancefloor as a place of refuge. When the time of transcendence ultimately arrives, Björk's eyes are definitely open. –Quinn Moreland

Listen: Björk, "Hyperballad"

Columbia

Leave it to Mariah Carey, the girl next door, to make pure lust sound so naive, so syrupy sweet, that it could be read as something pious to a passerby. Leave it to a diva at the height of her fame to describe being horny as feeling "kinda hectic inside," and to articulate it by singing more dizzying runs than an amusement park's worth of rides. It feels right that she wrote, produced, and recorded "Fantasy" in only two days, roughly the amount of time a person can live solely on the giddiness of a flirtation and the anticipation of an eventual release. Here's what love at 26, the age at which she put out the song, could feel like. It's what you want love to feel like for the rest of your life, too.

Mariah's ninth No. 1 came between hits from fellow icons Janet Jackson and Whitney Houston, outperforming both as a historical chart-topping record. "Fantasy" debuted at the top of the Hot 100, making Mariah the first woman to ever do so, and only the second artist to debut at No. 1 after Michael Jackson. Its foundation was a melding of genres—by reworking several elements from "Genius of Love," the 1981 Tom Tom Club track that was already becoming a staple in rap sample libraries, she and co-producer Dave Hall suggested that pop music could be just as sly, reverent, experimental, and flip as hip-hop. And the remix, produced by Diddy and his Bad Boy collective, served as their proof of concept.

By several accounts, it's a miracle that the remix exists at all. At the time, Mariah's infamously controlling label honcho husband, Tommy Mottola, 20 years her senior, had hoped to make a family-friendly balladeer out of the singer. He didn't want her sullying her pristine image, never mind at the hands of a rapper who performed under the name Ol’ Dirty Bastard. (Later in life, the singer would open up about how she, a light-skinned Black woman, was marketed by her label in ways that felt out of her control.) But Mariah, a superfan of Wu-Tang's 36 Chambers who was known to blast ODB on a pink boombox while riding around in her limo, insisted that the rapper be given free rein. It became a spectacle, involving exorbitant amounts of money at the time—$15,000 for a verse—and several very drunk studio sessions.

And so ODB became the song's ringmaster, opening with what would become one of the most recognizable callouts in block party history, ambling in and out of the song with a swaggering charm, inevitably swerving so hard that his drawl becomes a little bit country, a little bit rock’n’roll. It was chaos, it was genius, it made for a remix so successful that it ended up being responsible for half of the song's insane sales. But the song also became something much more powerful for Mariah and those who would follow her: It was a declaration of independence, a reclamation of agency and identity, a blueprint for a new kind of pop song that would be replicated for decades to come. –Puja Patel

Listen: Mariah Carey, "Fantasy (Remix)" [ft. Ol’ Dirty Bastard]