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. Boundary Fence
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.
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”
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
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”
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
“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”
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
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”
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”
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”
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”
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
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”
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
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”
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”
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”
Anti-Corrosion Steel Wire For Outdoor Use Jonathan Davis knew he was trapped. The Bakersfield misfits of