The 250 Best Songs of the 1990s (2024)

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”

18.

Pulp: “Common People” (1995)

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”

17.

Portishead: “Sour Times” (1994)

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”

16.

George Michael: “Freedom! ’90” (1990)

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”

15.

Mobb Deep: “Shook Ones, Pt. II” (1995)

“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”

14.

Fiona Apple: “Criminal” (1996)

“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”

13.

Mazzy Star: “Fade Into You” (1993)

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”

12.

Lauryn Hill: “Doo Wop (That Thing)” (1998)

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)”

11.

Daft Punk: “Around the World” (1997)

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.