The 100 Best Singles of the 1990s

40. The Cardigans, “Lovefool”

Maybe because its popularity in the U.S. was in part predicated on its inclusion on the zeitgeisty soundtrack to Baz Luhrmann’s William Shakespeare’s Romeo + Juliet, Swedish band the Cardigans’s hit “Lovefool” is remembered as one of our generations most valiant stabs at post-irony. Nice try. Did anyone actually listen to those lyrics? While there’s no question that the basement-disco pulse seems as innocent as a pink-penned note reading “Do you like me? Check ‘Yes’ or ‘No,’” the sinking desperation of the chorus tells a creepier tale, especially for anyone who has, in real life, been told, “Pretend you’re a necrophiliac” Henderson

39. En Vogue, “My Lovin’ (You’re Never Gonna Get It)”

And now it’s time for a breakdown. New Jack stepped aside for New Jill thanks in large part to the ubiquity of the funky divas’ sweetly harmonizing summer juggernaut. As though it had any choice in the matter. In true if-it-ain’t-broke fashion, “My Lovin’” returns to the same James Brown jam (“The Payback”) that set it off for the quartet at the decade’s open with “Hold On,” only this time around, the arms that held onto their love have grown weary of grasping at air—or have grown tired of flashing the finger of shame. En Vogue toyingly vacillate between second- and third-person so that you’re never quite sure whether they’re speaking on their one or someone else’s behalf. The groove is so all-encompassing, it’s probably both. Henderson

38. The Cranberries, “Linger”

Nowhere does novelty carry more weight with critics than in retrospectives like this one. Identifying songs that are path-breaking or influential in addition to being enjoyable in their own right seems like one of the only sure ways to tell the great songs from the merely very good. But the case for a song like “Linger” is mushy subjectivity all the way down. There’s nothing here that the Smiths or the Stone Roses didn’t do first, and so the song keeps or forfeits its spot in the canon entirely on the strength of Noel Hogan’s hooks and Dolores O’Riordan’s singing. And what strengths those are. In terms of its structure and pacing, “Linger” is a triumph of pop engineering, but the majestic interplay between orchestral strings and acoustic guitars is more alchemy than science, and the way that O’Riordan draws out “You’ve got me wrapped around your finger” so that the last word alone becomes the song’s best hook. Well, that’s pure magic. Cole

37. Radiohead, “Creep”

Long before they were the saviors of rock, Radiohead was a bunch of a loner weirdos, and Thom Yorke was their misfit leader, pining for a girl he could only approach via song. That song is rivaled only by “Every Breath You Take” as the ultimate kind-of-obsessive/kind-of-romantic crush anthem, with guitarist Jonny Greenwood’s perfectly timed blasts of electricity turning it from slightly creepy to threatening. And has any other verse ever captured the narcissistic self-loathing that is the essence of unrequited love better than “I want to have control/I want a perfect body/I want a perfect soul/I want you to notice when I’m not around/You’re so fucking special/I wish I was special”? Cinquemani

36. Madonna, “Deeper and Deeper”

Among Madonna’s finest achievements, the angsty pop anthem “Deeper and Deeper” is both an acute distillation of Erotica’s smut-glam decadence and the singer’s lifelong blond ambition. The song, like its video, practically plays out as an autobiography of the singer’s life: Atop sambalicious disco, Madonna delivers a burning, poignant fairy tale of yearning and escape in which she plays both Little Red Riding Hood and the Big Bad Wolf. Armond White once praised Madonna for how she took “outsider art inside herself”—which is to say, justified it by personalizing it. The uncontrolled, fierce tension of the song derives from the feeling that Madonna is taking a plunge into some hedonistic abyss of her own liberated, uninhibited making. Gonzalez

35. Björk, “Jóga”

With “Jóga,” the lead single from her third album, Homogenic, Björk practically invented baroque electronica. Though the song is an ode to her homeland and best friend (for whom the track is titled), and features one of the Icelandic singer-songwriter’s fiercest vocal performances to date (a “state of emergency,” indeed), Björk’s sweeping string arrangement is its true star. Aside from some subtle electronic skittering, Björk and producer Mark Bell’s volcanic beats don’t even erupt completely until two minutes in—proof that, while she’s become the undisputed queen of electronic pop, genre is simply another manmade construct for which Björk has no use. Cinquemani

34. Madonna, “Erotica”

Madonna accepts the burden of her throaty, spent-from-touring voice, which makes Erotica’s taunting, aggressive lyrics—an elaborate exploration of sex, from seduction to disease—feel unmistakably honest. The title track, whose opening put-a-record-on scratchiness mirrors that of Madonna’s most divisive instrument, is the singer’s invitation to the dance, a slithering, sinister snake rising from a gaudily ornate chalice. The beats are, by design, hypnotic—at once alluring and devious. With “Erotica,” Madonna promises to get you off, but not without giving you something. Gonzalez

33. Blur, “Song 2”

While cheeky pop-rock has been big business in the U.K. since, at least, the Smiths, we Americans take our Brit rock earnest and anthemic, and the more so the better: Oasis was a big deal, Radiohead was a bigger deal, and alas, there seems to be no escaping Coldplay. Blur’s “Song 2” was nothing if not anthemic, but ‘90s rock didn’t come any snarkier. A sneering send-up of American grunge, “Song 2” cut its sardonic lyrics with a cascade of power chords and a brainless “Woo-hoo!” chorus that sounded awesome no matter how many car commercials we heard it on. As it turned out, Damon Albarn at his dumbest was also his least dispensable, which maybe explains why he never held Americans’ attention in the same way until he started playing electro-pop with a band of cartoon characters. Cole

32. U2, “One”

The cool allure of “One” is evident just from its opening riff, where the Edge’s easy, liquid guitar manages somehow to sizzle and slither in the brief space of a few notes. Gaining even more mystique for purportedly inspiring a weary U2 to avoid a breakup, the bluesy, slow-burning ballad remains one of the band’s finest efforts at grand, emotive rock. Without resorting to the anthemic clichés that came to define them in the decade that followed, Bono and company simultaneously deliver intimacy, power, and precision, taking the conflicted premise of “With or Without You” to more mature, and infinitely more graceful, heights. Liedel

31. Massive Attack, “Teardrop”

Like hardcore and grunge before it, trip-hop seemed fated to express a particular zeitgeist—in this case, “pre-millennial tension,” a specifically yuppie-ish subgenre of regular old angst that made crowded cities and computers into signifiers of abject dread. Massive Attack’s Mezzanine is a near-perfect distillation of that generational malaise—all of it, that is, except for “Teardrop,” an oasis of emotional directness in a song cycle preoccupied with mechanical alienation. Massive Attack’s typical claustrophobia is swapped out for a spacious, piano-based arrangement, while Elizabeth Fraser’s most unaffectedly human vocal performance to date is as hypnotic as anything she did with the Cocteau Twins. Massive Attack spent the ‘90s articulating their generation’s directionless foreboding, but with “Teardrop,” they did what they could to soothe it. Cole