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The 100 Best Singles of the 1990s

Is it fair to say that many of us attach no actual “nostalgia,” in the strictest sense of the word, to the singles of the 1990s?

The 100 Best Singles of the 1990s
Photo: Warner Bros.

Is it fair to say that many of us attach no actual “nostalgia,” in the strictest sense of the word, to the singles of the 1990s? In one putrid sense, the decade began with back-to-back number one hits from Phil Collins and Michael Bolton. And if that tidbit weren’t enough to boot you off the good-time train trip alongside memory lane, you could still arguably never compete with the decade itself in terms of how much it deified the past. The first time I heard “Vogue” on the radio, I wondered why my local pop music station was playing a disco song from 1978. And need I mention that few songs sat at the top of the charts in the ’90s longer than a 1973 ditty by Elton John?

Maybe it was simply that the ’90s represented nostalgia’s last big blowout in tandem with the death throes of physical media. In a more philosophical sense, the decade ended just as MP3 culture was really starting to forever change the way singles operate in our lives. Consequently, the songs that so many of us cherished in the ’90s lived on in our own personal “shuffle play” soundtracks long after the likes of Janet Jackson, Prince, and Alanis Morissette couldn’t land a Billboard number one hit for love or money.

Many of the songs on this list don’t actually feel like part of our past, but still linger as representations of our eternal present. And yet it’s sort of impossible to not feel a twinge of nostalgia for the finitude of solid-matter, extended-play singles with copious remixes, to feel gratitude for the chemically balanced variety that emerged from the rigid discipline—and, yes, probably payola—of radio DJ charts.

More to the point, the ’90s may have been the last full decade during which stepping outside of the box to broaden one’s musical horizons was not necessarily the given—whereas the iPod era has turned us all into active musical scavengers, always seeking out the next obscure download. With perfectly acceptable gems right at the heart of the mainstream (Nirvana’s “Come As You Are,” Deee-Lite’s “Groove Is in the Heart,” Aaliyah’s “Are You That Somebody?”), who even wanted to entertain wanderlust? Eric Henderson


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100. Sophie B. Hawkins, “Damn I Wish I Was Your lover”

Sophie B. Hawkins’s debut single starts off discreetly enough, with the sound of New York’s underground, the soft shuffle of a drum loop, and an opening line worthy of Prince: “That old dog has chained you up all right” Prince, in fact, could have written the song himself, except Hawkins took the sentiment of songs like the Purple One’s “I Wanna Be Your Lover” to grittier, even ballsier territory. One part Led Zeppelin, one part Rolling Stones, and a whole lot of female fortitude, “Damn I Wish I Was Your Lover” was the most tenacious unrequited-love song of the decade—or maybe ever. Sal Cinquemani

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99. Stardust, “Music Sounds Bettter with You”

That disco never died was obvious. But for a couple of decades, it wore a number of masks to hide its true identity. Until, that is, the late ’90s, when it ditched all façades, did some speed and made its triumphant return under the banner “filtered disco” And when it returned, it did so with a vengeance. Proudly flaunting the same elements that irritated disco’s critics the first time around, filtered disco was fruity, repetitive, BPM-addled, and knowingly stupid. The most mercilessly entertaining entry was this one-off from Daft Punk’s Thomas Bangalter, an exhilarating hit of dance-floor cocaine with a sugary rhythm guitar, a subterranean-deep bassline, and one of dance music’s all-time great autocritiques: “Ooh, baby, I feel right/I feel like the music sounds better with you” Henderson


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98. Arrested Development, “Tennessee”

Perhaps no other track from the early ’90s provided better (or catchier) proof that hip-hop was more versatile and capable than prevailing gangster-rap themes than Arrested Development’s “Tennessee,” its stuttering drumline ably providing a clean backdrop for expositions on civil rights, genealogical discovery, Southern culture, the devastating legacy of slavery, and the nature of God. A pained but uplifting narrative struggles at times to catch up with the song’s driving gait, but “Tennessee” satisfies nonetheless, mixing raw, percussive power, quirky sampling, and inspirational imagery into one cerebral whole. Kevin Liedel


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97. Ice Cube, “It Was a Good Day”

“It Was a Good Day” stands out in Ice Cube’s catalogue for its rare focus on things that have gone well in his L.A. hood, noting that nobody he knows got killed as an exception to his usual daily grind. But it also predicts the family-friendly positivity that he would become known for just a decade later. The talk about pickup games of basketball and self-promoting Goodyear blimps and that smooth Isley Brothers sample that lays down the groove all eventually gave way to the good-natured positivity of a film career that includes kids flicks like Are We There Yet? and the Barbershop franchise. A brilliant standalone single, “It Was a Good Day” marked the turning point from Ice Cube’s militant gangsta-rap past toward a much more easygoing future. Jonathan Keefe


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96. The Stone Roses, “I Wanna Be Adored”

The Stone Roses forged the blueprint for the Britpop movement for a number of reasons: Not only did they fly the flag for organic, guitar-driven British music in a time where an increasing number of artists were reaching for their turntables, but Ian Brown’s extraordinarily cocksure attitude gave license for the Gallaghers, Albarns, and Andersons of the scene to strut around saying and doing whatever they pleased. “I Wanna Be Adored” channels this attitude into a swaggering, militant anthem, its slight word count (clocking in at just 19) only further amplifying the resonance they feel this message deserves. If you ever witnessed a brassy twentysomething marching down your street with his chest pushed outward, there’s a good chance he was marching to the tune of “I Wanna Be Adored” Huw Jones

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95. Underworld, “Born Slippy (Nuxx)”

Who’s that boy? He’s dirty and numb but also capable of angelic poses. He’s also terribly fond of lager, chemicals, and blondes. Sounds a bit like the libidinous bugger Ewan McGregor played in Danny Boyle’s Trainspotting, the film that made this dark, long, chest-puffing techno anthem ubiquitous for a hot second back in 1996. Like Benton’s craving for smack, the beats are frantic, dizzying, ravenous, even pained, rippling outward like ginormous waves or cascading ribbons made of steel, grasping for the sort of ecstasy that seems to only come with absolute annihilation. Such is the gnarliness of Underworld’s music. Ed Gonzalez


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94. The Cure, “Pictures of You”

It’s a shame that the Cure has spent so much of their three-decade career relegated to cult-act marginality, their music preemptively dismissed as mope material for dour goth types even as Robert Smith and company have turned out some of the most lavish and heartbreaking pop of their generation. They’re bigger than any clique, and “Pictures of You” saw them achieving a level of universality that their more marketable peers should envy. Pop lyrics have rarely conveyed longing in more relatable terms than Smith’s opening line (“I’ve been staring so long at these pictures of you/That I almost believe that they’re real”), and in the following seven minutes the Cure provide elegant catharsis for all the heartbroken, even those who have never spent a cent of their income on black hair dye. Matthew Cole


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93. Daft Punk, “Da Funk”

Though I’d like to stress I’m part of that small percentage of the general public who went on to become full-fledged Daft Punk fans, like many listeners, I was first endeared to “Da Funk” by the talking dog who blares it from his ghetto blaster in Spike Jonze’s music video for the song. I’m sure this was a very calculated point in the single’s marketing process, because it’s clear that some instrumental tracks need to find a sense of character in order to connect with mainstream audiences. Ingeniously, Charles the dog provided “Da Funk” with just that. The lashings of trashy disco and that throbbing bass needed something (or someone) to humanise its filthy neo-funk, and Charles did just that. Jones


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92. Sheryl Crow, “If It Makes You Happy”

After allegations that she was simply a pretty mouthpiece for her Tuesday Night Music Club, Sheryl Crow had a lot to prove with her sophomore effort. Originally conceived as a country song by co-writer Jeff Trott, the self-produced lead single, “If It Makes You Happy,” was a pointed departure from the gin-soaked roots-pop of Tuesday Night Music Club, starting with its heavy electric guitar riff and plodding drum beat, but not ending there. Crow’s lyrics are a reflection on the massive success of her debut, with her stint at the muddy, mosquito-ridden Woodstock ’94 festival serving as a metaphorical narrative for the stinging accusations and acrimony that followed. Cinquemani

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91. Pavement, “Cut Your Hair”

A forceful middle finger to both the end of hair metal and to the emergence of grunge, Pavement’s “Cut Your Hair” is as relevant today as it was nearly 20 years ago. The indie posturing of today’s music scene is, of course, every bit as image-driven—and the mainstream appropriation of those images—is every bit as shallow as it was in 1994. “I don’t remember a word/But I don’t care, I care, I really don’t care/Did you see the drummer’s hair” are the bitter words of the outsider Stephen Malkmus always had been and always would remain, a cynical assessment of how the machinery of the music industry had broken and a reminder that it’s probably beyond repair. Keefe


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90. The B-52’s, “Roam”

Cosmic Thing, an unexpected commercial smash for the B-52’s, derives its beauty from the band’s sincere belief in the healing power of their unbridled goofiness. The album’s happy-go-luckiness may feel indulgent across the album’s 10 tracks, but after the death of Ricky Wilson, the band earned the right to dance their mess around—or as Robert Cristgau perfectly put it, “dance away from the edge of ecocatastrophe” “Roam” is, on the surface, a hippy-dippy tribe’s ode to love and travel, a kissing cousin to the band’s “Revolution Earth,” but the band isn’t simply promoting the sights of ancient and modern world wonders. They may advocate “without wings, without wheels,” but Kate Pierson and Cindy Wilson’s ecstatic harmonies confirm that this is the sound of angels convening, asking everyone to travel within. Gonzalez


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89. U2, “Mysterious Ways”

Bono believes in many things, many unachievable, among them world peace, but he’s always sounded less full of it when he sticks to matters of the heart—not unlike literature’s rock star, Salman Rushdie, who once praised Bono for crossing similar frontiers (physical, social, intellectual, and artistic). “Mysterious Ways” is a canny marriage of mystical lyricism and unexpectedly funky, conga-infused percussion, and it is to U2 what The Moor’s Last Sigh is to Rushdie, a gushingly lovelorn ode to isolation and salvation through the love of a woman. The song’s idealistic romanticism would be unforgivable, almost insulting, if Bono’s knees-to-the-floor vocal performance wasn’t so committed or if the production—a marriage of modern and practically ancient styles—didn’t suggest the eternal struggle of love and lust. This is pop music’s idea of a Dead Sea Scroll. Gonzalez


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88. Nirvana, “Heart-Shaped Box”

Whether a fossilized relic of the Kurt and Courtney martial saga or an angry paean to children stricken with cancer, the raging torrent of “Heart-Shaped Box” remains one of Nirvana’s most precisely heated songs. Fitted with the standard trappings of Cobain’s stylized delivery, where boredom and sarcasm clash with simmering rage, its fuzz-drenched landscape is supplemented by the tumbling progression of Dave Grohl’s clobbered drums, a thick bassline, and the tug of war between fuzzy rhythm guitar and searing lead, making it one of the hardest songs on an album packed with barely concealed fury. Jesse Cataldo

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87. Lauryn Hill, “Lost Ones”

The rhymes are tight, her patois is on point, the beats are thick, and the hook is easy on the ears. With that out of the way, who exactly is “Lost Ones” about? Wyclef? Pras? Both? No matter. As the opener to The Miseducation of Lauryn Hill, the track serves as a palatte cleanser of sorts, a wiping of the slate, a warning not to fuck with L. Boogie so that she can get down to the business of sizing herself up. It’s the song that announced Hill’s arrival as a force to be reckoned with—at least for a year or two. Cinquemani


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86. Zhané, “Hey Mr. DJ”

Straight-up, no-bullshit dance music. The duo pronounced “Jah-Nay” let the slack groove thang take you away to a place where the DJ will keep playing that song all night. And even if he or she doesn’t, don’t worry. There’s still a bunch of good SWV, Jade, and Jomanda in the crate to keep you going on and on and on. With a brilliantly repurposed sample from the lesser-known Michael Wycoff quiet-storm classic “Looking Up to You,” “Hey Mr. DJ” is equal parts new jack, disco, and soul, and the brew is intoxicating without any mitigating side effects. Zhané turns the song into their own triumphant answer to Soul II Soul’s inquiry, “However do you want me?” Henderson


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85. Nirvana, “Come As You Are”

A stark contrast from Nevermind’s “Smells Like Teen Spirit,” the slow-tempoed, unassuming “Come As You Are” is taut with a seething derision that boils right below its surface, and perhaps no other Nirvana track better captures the ambiguity of Cobain’s satirical wit. The doubling of guitars and vocals throughout also lends the song a menacing apathy, with the band trading in the hammering, fast-paced approach for something altogether more deliberate and cryptic. That haunting quality is, of course, unforgettably aided in part by Cobain’s now-prescient line, part reassurance and part threat: “I swear that I don’t have a gun” Liedel


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84. Jay-Z, “Hard Knock Life (Ghetto Anthem)”

Jay-Z’s co-opting of a discordant, already famous showtune is a rare novel endeavor in a genre generally defined by following the leader; it’s pulled off so seamlessly that it’s easy to forget what a ballsy move it was. The transformation of the original’s piano base into a thumping organ creep sets the stage, but it’s undeniably Jay-Z, transparently showing off his executive command by fussing with the levels at the start, which makes the song. The source material and the resulting product may seem diametrically opposed, but they end up being fundamentally about the same thing: forming a common thread of struggles with poverty spun into gold. Cataldo

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83. Michael Jackson & Janet Jackson, “Scream”

Jacko was reportedly a huge fan of his sister’s work with Jimmy Jam and Terry Lewis, specifically “Rhythm Nation” So it’s no surprise that he would hire the duo to produce for him; what’s surprising is that it took so long. “Scream” is an unrelenting techno-funk workout with the warm, layered harmonies both siblings were known for sheathed beneath clipped, sterile synth beats and swaths of metal guitar. This was nothing new for Michael, being similar in style to his single “Jam,” but he adopted an even angstier tone here, spitting out lyrics aimed at the media’s handling of his sex abuse trial with a vitriol not previously heard. The only moment of release comes during Janet’s hushed vocal bridge, in which she demurely marvels in disgust at “all the injustice” Cinquemani


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82. Pavement, “Summer Babe”

A love song reduced to its barest elements, “Summer Babe” is all feeble, trebly guitar and untrammeled despondency, the nonexistent relationship between its queasy narrator and his icy dream woman functioning as a representation of the gulf between the band and pop’s sunnier climes, where boy and girl unite beautifully and effortlessly. On the surface, this seems like a messy, half-assed song, full of loose ends and mumbly vocal drop-offs. But its genius at channeling despair into something that’s witty and wise makes the song a classic, its self-deprecating dejection jibing perfectly with the slack disarray of the music. Cataldo


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81. Depeche Mode, “Personal Jesus”

Depeche Mode’s gimmick is one that, after years of repetition, seems ingeniously flimsy, bundling angst and spiritual frustration with sex and pouty gloom. “Personal Jesus” has escaped the mustiness that has enveloped most of the band’s material not by flouting these tactics, but by embodying them so well. Bolstered by Dave Gahan’s repeated imprecation to “reach out and touch faith,” the vocals seem perched on a neutral point between the completely earnest and the bitterly sarcastic, turning what could have been another flat religious diatribe into a thinly dual-tiered assessment of devotion and self-absorption. Cataldo


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80. Robin S., “Show Me Love”

A colleague’s all-stomping impersonation of “Show Me Love”—delivered with great fanfare whenever anyone plays this song within a 50-foot earshot—is just about the best defense one can make for this pop-house smash. With the courage and conviction of a drag queen who’s perilously late for the society ball, Robin S. flamboyantly applies her LaBellian grunting to an aggressive production of minimal thumping to produce the ass-iest of come-hither anthems. It’s the “ugliest” song on on our list—and it’s amazing for it. Gonzalez

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79. Soundgarden, “Black Hole Sun”

The restrained but psychedelic beauty of “Black Hole Sun” was not only a departure for Soundgarden, but for grunge at large, indicative of the Seattle sound’s transformation into a newly mainstream alternative genre. The track endures beyond its implications on ’90s rock though: Surreal, illusory, and perhaps even seductive, “Black Hole Sun” delivers sinister imagery with its slow-churning rhythm, acting as an ideal foil for Chris Cornell’s searing vocals and playful, scripture-inspired lyrics. “Times are gone for honest men,” he mutters like a bitter preacher, but with a wink: “And sometimes far too long for snakes” Liedel


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78. Oasis, “Wonderwall”

The pugnacious artistry of the notoriously feisty Gallagher brothers is on full display in “Wonderwall,” Oasis’s first single to make waves on the U.S. pop charts. Despite its airy, even gentle four-chord acoustic intro and string accompaniments, the song is a particularly belligerent and point-blank ballad, roughly spat with an almost whiny glee by Liam Gallagher. It remains one of Oasis’s best and most influential efforts to date—an encapsulation of the poppy, authentically English bravado the group brought to the alternative scene, and helping to spur on a mid-decade Britpop invasion that included bands like Supergrass and Elastica. Liedel


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77. Portishead, “Sour Times”

The ’90s were a fantastic time for morose, woe-is-me music. Disaffect and angst were in, and countless bands were able to cash in on the collective misery and self-pitying teenage mope. But few acts were able to elevate this to a real artful aesthetic the way Portishead did. Their depression cut deeper than that of, say, Garbage, and tracks like “Sour Times” translated that dysthymia into moody, minimalist trip-hop soundscapes. Gasping through lines about how nobody loves her, Beth Gibbons sounds like she has a straight razor held to her forearm, and it’s that on-the-precipice tension that makes “Sour Times” so miserable and so compelling. Keefe


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76. Us3, “Cantaloop (Flip Fantasia)”

They got the beats. They got the rhymes. Us3’s sole pop hit, “Cantaloop (Flip Fantasia),” is a cheerfully funky fusion of jazz and hip-hop—nothing more, nothing less. What it lacks in social consciousness it makes up for in musical brinkmanship: The production’s exciting explosion of frenetic horn riffs, interrupted only by a sick trumpet solo by Gerard Presencer, samples Herbie Hancock and Lou Donaldson, among others, and grooves in scary synchronicity with the uncannily delivered lyrics by one-time member Rahsaan Kelly. The mood is creative, idealistic, and laidback, suggesting the good vibes of A Tribe Called Quest and Digable Planets. It’s a sweet, slick, funky maelstrom of sound that’s also a time capsule of a gorgeously short-lived musical form. Diddi-diddi bop. Gonzalez

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75. The Notorious B.I.G., “Hypnotize”

Few rappers could play the boss as effectively as Biggie, his outsized frame, ever-present cigar, and ridiculous suits matched by one of the most commanding voices in hip-hop. “Hypnotize” found him at the height of these powers, from his opening “Hah!” to the crawling bassline that drags the song down to meet his laconic pace. Few rap songs have the nerve to move this slowly, or function this sparely, with so little moving in the foreground that even Puff Daddy’s hushed ad-libs, normally a unremitted nuisance, feel like wispy atmospheric shading. Cataldo


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74. Neutral Milk Hotel, “Holland, 1945”

Hopping from war-torn Europe to modern-day Spain to outer space, “Holland, 1945” spins its World War II reference points into a vibrant, colorful tapestry that never forgets the insistent horror lingering at its core. The most directly biographical track on an album morbidly fixated on Anne Frank’s sad fate, the song bitterly whimpers for a world where death and rot are routinely chosen over life and happiness, a challenge that might feel ineffectual were it not backed by an overdriven guitar and the full weight of the band’s rhythm section. Cataldo


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73. Nirvana, “Lithium”

Confession: I couldn’t have been more tardy to the party when it comes to recognizing the impact of Nirvana on pop music. “Lithium” was always my favorite of their songs because it was the one they performed on the MTV Video Music Awards and I loved watching Krist Novoselic take a dinger to the head after tossing his bass guitar up in the air, and was entirely in Dave Grohl’s corner as he mockingly yelled “Hi, Axl!” at the end of their performance. It wasn’t until years later that I came to realize I had also been responding to the elegance of Kurt Cobain’s songwriting. Attitude counts for a lot, but you can’t fake that galvanizing modulation into the chorus’s minor key bitterness: “I love you, I’m not gonna crack” Henderson


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72. White Town, “Your Woman”

A one-hit wonder whose other material totally justifies that status, White Town stumbled into a moment of sheer brilliance on “Your Woman,” a single that married a fucked-up horn sample to a funk rhythm section straight out of Prince’s playbook. The sheer catchiness of the song’s arrangement got some adventurous radio programmers on board, but it was the say-what-now gender politics of the song’s lyrics that proved to be most compelling. Hearing Jyoti Mishra’s plaintive tenor croon, “I guess what they say is true/I could never be the right kind of girl for you/I could never be your woman,” remains one of the most subversive moments in ’90s pop. Keefe

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71. Snoop Doggy Dogg, “Gin and Juice”

If “Who Am I (What’s My Name)?” was Snoop Doggy Dogg’s explicit introduction as a solo artist, then this second single from Doggystyle shed similarly explicit light on his everyday exploits: “Rollin’ down the street, smokin’ indo, sippin’ on gin and juice/Laid back” This snapshot of L.A. lifestyle became a certified G-Funk anthem, served with what had by then become the genre’s token staples. Snoop’s easy-rolling drawl provided the ideal accompaniment to Dr. Dre’s whistling keyboards and rumbling basslines, with “Gin and Juice” yet another indication that—together—these two could do absolutely nothing wrong. Jones


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70. Nas, “The World Is Yours”

One of the best examples of a song built on and entirely sustained by a sample, “The World Is Yours” owes almost as much to producer Pete Rock’s tiny Ahmad Jamal snippet as it does to Nas. Borrowing almost exclusively from the jazz pianist’s “I Love Music” while snatching a title from Pan Am’s famous slogan, the song is a wonder of economy, allowing additional time only for a few scratch breakdowns beneath the vocals. The spare backing gives Nas ample space to theorize and motivate while also grounding his loftier tendencies, avoiding the condescending preachiness that poisoned so many of his later tracks. Cataldo


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69. The Notorious B.I.G., “Mo Money Mo Problems”

Biggie’s second posthumous #1 single did more than secure the East Coast MC’s place in the rap history books: It ushered in an age where a street-hardened rapper could be a full-stop pop star (Jay-Z, T.I., Lil Wayne: You’re welcome). Chris Rock called “Mo Money Mo Problems” the most popular song that almost no one could relate to, but he’s only right if we believe that Biggie, Ma$e, and Puff Daddy actually regretted their good fortunes. The Diana Ross sample and the terminally catchy Kelly Price chorus spell slim chances for that hypothesis, suffusing the track with too much joy to be read as a straightforward wish for simpler times. Mixing optimism with pragmatic grit, Biggie’s last great single is an anthem for “true players”: the guys who refuse to let haters and fair-weather friends spoil their success. Cole


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68. Smashing Pumpkins, “Tonight, Tonight”

Songs by Smashing Pumpkins generally fall within easily definable extremes, erring either on the side of nasty snarl or heady romanticism. This is the peak of the latter, a magical track that whips itself up into a frothy orchestral bluster. Jimmy Chamberlain’s greatest contribution comes in the form of a surging series of drumrolls, which match the ascending strings, as the guitar, usually the band’s dominant voice, lies mostly dormant. Even Billy Corgan’s reedy instrument is urged into higher registers by the climax, which reaches heights the band would never challenge again. Cataldo

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67. The Orb, “Little Fluffy Clouds”

Standing in stark contrast to the premillennial tension that marked most of the decade’s great dance music, the Orb’s “Little Fluffy Clouds” posits the ghost in the machine to be none other than Casper. As the vocals suggest, Alex Paterson earns frequent-flyer miles by merely “layering different sounds on top of one another,” with Ricky Lee Jones droning on about the skies in Arizona as guitars sampled from Steve Reich turn a stuttering snare roll into a purple, red, and yellow summer panorama. Rarely has electronica achieved a delicacy like this. You don’t hear music like this anymore, not even in the desert. Henderson


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66. Prince and the New Power Generation, “7”

A Bible verse as related by a New World prince, “7” is a lush allegory for the perils of romantic strife, set across deserts and streets of gold and featuring armies, plagues, and angels. Among the fiercest tracks from Prince and the New Power Generation’s Love Symbol Album, this rock soap opera is a predictable cock-storm of funk, the One and Only’s vulnerable, emotion-rich falsetto wielding the same blunt-force trauma as the swords and tambourines that are dropped into the production with the sort of timing that would be corny if it weren’t so swoony. Way before he takes it to church, Prince’s intellect and savoir-faire has saved the day. Gonzalez


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65. Belle and Sebastian, “Lazy Line Painter Jane”

Put a gun to my head, and it’s a toss-up between the Ronettes’s “Be My Baby” and “Lazy Line Painter Jane” as my favorite pop song ever, and I owe it all to Emily Gould, the ex-Gawker editor and infamous Jimmy Kimmel sparring partner who first played the song for me while hanging out in the room she shared with a friend of mine during our sophomore year at Kenyon. Listening to the single’s ebullient handclaps, “Boo to the business world!” proclamations, soaring B-section melody, and hetero-flexible lyrical hook, that year in college sucked just a little bit less for five glorious minutes thanks to the power of a note-perfect pop song. Keefe


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64. The Prodigy, “Smack My Bitch Up”

Many struggled not to dismiss “Smack My Bitch Up” as extreme misogyny set to a boisterous jungle beat, even with the twist at the end of its music video or the fact that women on dance floors everywhere would gladly throw their hands in the air and sing along to its direct and clearly audible punchline. And in many ways, the whirlwind of controversy surrounding these unrepeatable—though obviously not unprintable—lyrics conspired to detract from the fact that Liam Howlett had indeed forged an indelibly rousing dance number. This was a feral sound that needed a shocking centrepiece, and it found one, but history will remember “Smack My Bitch Up” for its controversy rather than its deranged, raucous groove. Jones

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63. Primal Scream, “Loaded”

If ever there was a man who summed up the Madchester culture’s desire to cut loose and party past the early hours, it’s quite ironic that it happened to be Peter Fonda. The truncated quote from The Wild Angels that kicks off “Loaded” is the perfect précis of life in the Madchester era—albeit out of context: “We wanna be free to do what we wanna do…And we wanna get loaded…And we wanna have a good time…We’re gonna have a party” This is followed by a sumptuous bout of horn-fuelled funk, a sonorous bassline, and powerful gospel vocals, which in effect plays like the perfect soundtrack to those wanting to get loaded, have a good time, and have a party. Jones


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62. Fugees, “Fu-Gee-La”

For most, “Fu-Gee-La” was their introduction to the Fugees, and in many ways, the song remains the most concise and adrenalized representation of the band’s unique musical and philosophical humanism. It’s the song that most audaciously justified their name. These highly adaptable and resourceful refugees made art out of appropriating often obscure lyrics and sounds, turning them more than 90 degrees, as in Lauryn Hill transforming the “Oooh la la la”-ing butterflies in Teena Marie’s stomach into a siren’s song of spiritual elation. I could do without the Charmin, but if I had their guts, I would tattoo their greatest line—“In the battle lost my finger, mic became my arm”—onto my body. Gonzalez


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61. Mariah Carey, “Fantasy”

Mariah’s “Fantasy” remains one of the finest examples of reworking an extensive sample into a fully realized pop masterpiece. The funky, warbling strains of Tom Tom Club’s “Genius of Love” come ringing through immediately, and there’s no great effort to disguise any of the borrowed elements. And though the stripped-down remix, which brilliantly entwines the bridge portions with O.D.B’s absurd rap (“Japan, are you in the house?”), is considered by some to be the definitive version, the original is escapism perfected, a summer bubblegum gem with a sweet, flawless vocal line driven by a diva in her prime. Liedel


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60. Public Enemy, “911 Is a Joke”

He started out as Public Enemy’s comic relief, a court jester with an oversized clock around his neck who could actually rap when he wanted to. And considering the extent to which he devolved into a pop-culture punchline, thanks to spawning the “Flavorverse” of trashy VH1 reality shows and sitting for an especially mean-spirited Comedy Central roast, it’s easy to forget that there was once a real wit behind Flavor Flav’s comedy. Nowhere is that more apparent than on the gallows humor of “911 Is a Joke,” a party jam that calls the LAPD out on its institutional racism. The line “They don’t care/’Cause they stay paid anyway” is loaded with genuine conflicts of class and race, and it takes actual skill—genius, even—to couch those issues as comedy. Keefe

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59. Björk, “All Is Full of Love”

Though it has been as oft-remixed as any other Björk single from the landmark Homogenic set, no version quite achieves the ethereal effect that the album mix of “All Is Full of Love” does. Coming off the tail-end of “Pluto,” a sonic threnody for a suicidal fan, Björk’s open-source, beat-free echo chamber is both absolution and resurrection. Building quietly from a warm hexadecimal hum that’s the diametric opposite of sensory deprivation, the song accrues momentum as Björk simultaneously frees herself from the burden of expectation until cascades of shimmering, opal-hued harpsichord notes emerge from a curtain of glimmering white noise. Henderson


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58. My Bloody Valentine, “To Here Knows When”

Among the most exquisite pieces of experimental rock ever recorded, “To Here Knows When” doesn’t quite encapsulate all that was great about My Bloody Valentine’s Loveless, but it comes close. The droning guitar licks, the hypnotic swirl of vocals, the simulated flurry of electronic sounds—it’s all here, and usually all at once. My Bloody Valentine could sometimes overwhelm the ears entirely, but “To Here Knows When” walks the line, never quite devolving into noise. A minute into the song, one of Kevin Shields’s guitar lines peals out like a jet plane engine while he and Belinda Butcher sigh in unison. It’s an evocative pairing of human and machine noises whose beauty is enhanced by the sonic density, by an underlying threat of unintelligibly which imbues even the most intimidating movements with a sense of fragility. Cole


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57. Pulp, “Common People”

An unashamed working-class anthem penned by Britain’s screwy poet laureate, “Common People” revelled in all of the grotty culture staples of which the nation became ironically proud in the ’90s. Britpop was conquering all in its path by 1995, which made this celebration of the humbler elements of Britain’s nine-to-five culture a refreshing shift away from the genre’s tendency for overblown pageantry. Jarvis Cocker spills the beans on a chance meeting with a well-to-do college student, and perfectly sums up Britain’s collective insecurities about punching above our weight and, on the other side of the coin, the joys in “slumming it” every now and again. Jones


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56. Blur, “Girls & Boys”

Were it merely a withering take on ’90s sexual omnivoresness, or a snappy vessel for the semi-ironic safe-sex message that seems to linger at its edges, Blur’s first hit might have seemed almost instantly stale. But it’s the tortuous, hypnotic hook, its roadblock arrangement standing in defiance of the song’s litany of throbbing motifs (stabbing guitar, pulsed hi-hat, bouncing synth) that cements the song as timeless. Challenging the limits of catchiness while remaining insistently unforgettable, the morass of the chorus stands out as one of the decade’s finest pop moments. Cataldo

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55. Weezer, “Buddy Holly”

They’ve always walked a fine line between designs on power-pop greatness and embarrassing novelty, and “Buddy Holly” is perhaps Weezer’s most deft balancing act. Years before nerd couture became an obnoxious celebrity trend, Rivers Cuomo and his wide-framed glasses turned “I look just like Buddy Holly” into a self-deprecating sing-along, deflecting some of the attention from his complicated relationship with his public image via the single’s Happy Days-inspired video. While it took a few more albums before Weezer finally jumped the shark, “Buddy Holly” stands as their punchiest hit. Keefe


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54. Smashing Pumpkins, “Disarm”

Smashing Pumpkins’s most personal song—essentially my MTV generation’s answer to “Cat’s in the Cradle”—proves that there’s a fine line between a serial killer and a singer. Because the cherub-faced Billy Corgan’s poetry is so often metaphoric, it makes sense that the song’s lyrics (namely “Cut that little child”) were thought to be about abortion, but “The killer in me is the killer in you” seems like the unmistakable cry of an abuse victim. The production suggests a gothic fairy tale, while Corgan’s vocal performance gives haunting expression not only to his feelings of perseverance, but to his obvious fears of repeating the worst chapters in his past. Gonzalez


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53. DJ Shadow, “Midnight in a Perfect World”

Either the most dour New Year’s celebration of all time or the most comfortably numbed comedown anthem ever. Either way, it’s the most fun you’ll ever have on the cusp of either falling asleep or passing out. DJ Shadow’s rhapsody in black stitches drum breaks from a number of tracks atop a liberal sample from Pekka Pohjola’s “The Madness Subsides,” and the result is a truly intoxicating bit of introspective sensationalism, a microcosmic slice from Shadow’s monstrous Endtroducing… LP, a skittering cascade of percussive interjections and, above all, a lumbering slow-motion fall into the muted bliss of a night well spent. Henderson


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52. Erykah Badu, “Tyrone”

Erykah Badu is sensitive about her art, but her laughter let’s you know that she has a sense of humor. That alone makes her one of our richest afrobellas. But Ms. Badu is more than that: her spoken-word technique is precise, her hooks uniquely catchy, her rhymes both sassy and assy. I could listen to her all day, and there was a time in 1997 when this playful admonishment of a cheap, selfish, unnamed boyfriend (Tyrone is the best friend she no doubt resents for encouraging his bad behavior) exhausted my last CD player. What’s especially marvelous about the song is that, while Badu makes clear that there’s no gray area here, her arrangements, structures, and harmonies are alive with possibility: Though she would have told Whitney that it’s not right and it’s not okay, she would have also given her a million ways to kick Bobby out the door. Gonzalez

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51. Alanis Morissette, “You Oughta Know”

In a seething, typically semi-delusional letter to Spin’s Bob Guccione Jr. in 1996, Courtney Love called Alanis Morissette “a Product of Madonnas [sic] Fatal Flaw, contrivance at every level.” What with Alanis being a former pop tart and with Wilson Phillips producer Glen Ballard on board as songwriting partner, it’s hard to disagree with Court’s assessment. But it’s not Alanis’s fault that she was able to harness the rage of a movement that had already sold itself out and spit out a perfect pop song that became the defining moment of ’90s Female Angst. That Hole was never able to sell 16 million must have been a jagged little pill to swallow. Cinquemani


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50. Public Enemy, “Welcome to the Terrordome”

So much of Public Enemy’s militant shtick now reads as bullshit, especially with Flava Flav dissolving into a minstrel-show stereotype and Chuck D relaxing into armchair radicalism. Yet it’s impossible to argue with something as mean and animated as “Welcome to the Terrordome,” so packed with jagged pieces that it’s hard to know where to focus. Fully exemplifying the group’s violent grab-bag sound, the samples here come fast and loose, shot into the mix with little regard for meaning or context. They contribute to an atmosphere that’s willingly chaotic, a twitching patchwork of found sounds, vocal clips, and misbegotten snatches of conversation. Cataldo


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49. Radiohead, “Fake Plastic Trees”

So what if Alicia Silverstone’s Cher Horowitz dismissed it as “the maudlin music of the university station” and asked, “What is it about college and cry-baby music?” There were a lot of things that Cher didn’t get, and Radiohead’s “Fake Plastic Trees” was chief among them. It’s a single that aims for epic and hits its mark dead-center, not because of Thom Yorke’s cryptic lyrics, but because of the slow-building crescendo of Jonny Greenwood’s guitars and the structural perfection of the arrangement. Just as Yorke sings, “I can’t help the feeling/I could blow through the ceiling,” the whole production does exactly that before gravity inevitably wears him out and brings it all back to Earth. Keefe


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48. Sonic Youth, “Kool Thing”

For a song that is essentially a vengeful invective against LL Cool J, the breezy, punchy “Kool Thing” is a largely angst-free slice of punk rock. The song would be many listeners’ first exposure to Sonic Youth, and the band did not disappoint: Kim Gordon smirks her way through the track’s aloof-cool vocal parts, fighting the growling pack of guitars and Chuck D’s wildly disjointed cameo for the spotlight. Together, the three parts construct the ultimate parody of fame-fueled chauvinism, and no matter the personal anecdote that fuels it, “Kool Thing” is a snarky, lead-in anthem for the decade’s irreverent youth. Liedel

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47. Jeff Buckley, “Last Goodbye”

The most commercially successful single of Jeff Buckley’s career, “Last Goodbye” has retained a purity that his version of “Hallelujah” has since lost after being whored across countless television montages and a string of woefully insincere cover versions. It’s easier, then, to turn to “Last Goodbye” as a fitting eulogy to his wonderful talent. Buckley’s singing is, perhaps, the area in which he was most gifted, and here he sashays between his gorgeous falsetto and a raw emotive power with what seems like relative ease. That few singers have since matched his extraordinary vocals proves that this was indeed no mean feat, and only further emphasizes the tragedy of losing such a glorious talent. Jones


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46. Erykah Badu, “On & On”

Boasting the roundest bassline since Digable Planets got cool like dat, “On & On” is Erykah Badu’s mission statement from a higher plane. Her money might be gone, she might be all alone, but she’s feeling high and mighty, and the siren song pours forth from her honeyed lips like a fount of alien wisdom. Backed by a languorously snapping, swinging backbeat and expansive, half-heard piano chords that repeatedly collapse back on themselves, “On & On” is as sonically introspective as its creator, a woman who can believably claim to have walked the entire cipher of Earth, clear her throat, utter “Goddammit, I’ma sing my song,” and still seem like she’s hiding more than she’s revealing. Henderson


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45. Michael Jackson, “Remember the Time”

Back before he lost “it” (that is, the ability to remain relevant and produce quality songs with a prolific ease only few could muster), MJ gave us gems like “Remember the Time” Jackson turns in his most sincere, low-key vocal performance since “She’s Out of My Life,” perfectly matching his delicate, unaffected voice with the song’s snappy funk percussion and razor-sharp jazz embellishments. But out of all its great qualities, the bittersweet but lighthearted dance track is most memorable for catching the King of Pop in a rare but refreshing state of candor, his voice managing to remain sincere without losing any of its beguiling qualities. Liedel


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44. Björk, “Bachelorette”

This is where we reach peak Björk: Debut and Post were nothing if not idiosyncratic, but on Homogenic, the Icelandic singer envisioned a genre all her own. “Bacheleorette” completes a triptych that began with “Human Behaviour” and continued with “Isobel,” and if the earlier songs demonstrate Björk’s continuous interest in the electronic and classical avant-garde, then “Bachelorette” shows her pursuing those influences to the outer limits of pop. Impressive as it is, the song’s cataclysmic arrangement of beats and strings is ultimately overshadowed by Björk’s searing vocal; typically restrained, she finally unleashes the cosmic wail that would power Vespertine and Medúlla’s most transcendent moments. I can’t imagine how anyone could hear this song and persist, as does much of the music press, in describing Björk as a pixie or a nymph. She sounds like she’s 10 stories tall. Cole

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43. Foo Fighters, “Everlong”

There’s a definite sense of irony in the fact that Dave Grohl had to return to his position behind the drum kit in order to finally escape from beneath Kurt Cobain’s giant shadow. His thunderous drumming on this song’s impassioned crescendo affords “Everlong” a balls-to-the-wall gravity that was missing in almost all of the Foo’s previous work, and this marked the point where the wider world began to take them seriously as a band. Of course, “Everlong” wasn’t all about the drumming: This was a beast of a single, starting and stopping with a series of delirious riffs and delectably somber verses. Jones


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42. Madonna, “Secret”

Despite the common misconception that she often sings about sex, Madonna’s songs aren’t always sexy. “Secret” is perhaps the finest exception to that rule. As it slinks along a simple R&B backbeat and an unfussy acoustic guitar figure, “Secret” is also one of the most organic-sounding singles of Madonna’s career, taking its sweet time to get where it’s going and not giving up too much along the way. The arrangement gets off on being withholding, and, at least for one glorious single, so does Madonna: When she sings, “You knew all along/What I never wanted to say,” she sounds positively rapturous. Keefe


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41. Fugees, “Killing Me Softly”

“Fu-Gee-La,” stern and topical, made Lauryn Hill, Wyclef Jean, and Pras Michel the faces of a new kind of hip-hop, but it was The Score’s second single, “Killing Me Softly,” that won them audiences who, prior to the song’s release, may never have cared about hip-hop of any variety. By reworking Roberta Flack’s classic “Killing Me Softly with His Song” into a spare and heartfelt showcase for Hill’s voice, the Fugees dropped their tough exterior and made personal the raw emotions that had always propped up their pleas on behalf of outcasts. Politically minded MCs have never been in short supply, but few have understood as clearly as the Fugees that hip-hop needs heart as much as it needs conscience and intellect. Cole


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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

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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


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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


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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


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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

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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


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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


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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


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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

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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


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30. George Michael, “Freedom 90”

On its surface, George Michael’s “Freedom 90” may have been a rejection of all things image, but when he sang, “There’s someone else I’ve got to be,” it was clear he was also struggling with a different kind of identity crisis. The message is obvious in retrospect: I’m here, I’m queer, get used to it. In the long run, Michael’s vow of loyalty (“I won’t let you down/I will not give you up/Gotta have some faith in the sound”) wasn’t reciprocated by the public, but “Freedom” is still one of the best soul songs of the decade, pairing his own approximation of James Brown’s “Funky Drummer” with piano, guitar, and a killer bassline. And if the song (and video) weren’t filled with enough references and symbols, its chorus also makes a nod to Michael’s former duet partner Aretha Franklin’s “Think (Freedom)”—the copyright infringement-avoiding difference being that the Queen of Soul’s final “freedom!” goes up while George’s, uh, goes down. Cinquemani


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29. Wu-Tang Clan, “Protect Ya Neck”

The Wu-Tang Clan were the certified kings of belligerent posse rap, and “Protect Ya Neck” was quite possibly the jewel in their crown. From Inspectah Deck down, the track is choc-a-bloc with unorthodox rhyme schemes and some truly awe-inspiring wordplay. Deck stands out for his reference-heavy introduction: “I smoke on the mic like smokin’ Joe Frazier/The hellraiser, raisin’ hell with the flavor/Terrorize a jam like troops in Pakistan/Swingin’ through your town like your neighbourhood Spider-Man” Everything from this moment on is just a formality, the bar set exceedingly high and rolling on with an unremitting momentum. Jones


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28. Mazzy Star, “Fade into You”

In the early ’90s, it seemed like anything was possible—at least on pop radio. Anything including a folky waltz like psychedelic dream-pop band Mazzy Star’s “Fade Into You” crossing over from the mod rock charts to mainstream radio in a big way. With singer Hope Sandoval’s plaintive, listless vocals and an arrangement in which pedal steel and slide guitar figure prominently, the song was an unlikely hit, but one that, among a slew of alt-rock one-hit wonders that emerged in the early-to-mid ’90s, was able to transcend its era’s trappings thanks, in part, to its classic structure and timeless melody. Cinquemani

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27. Radiohead, “Paranoid Android”

The world’s first glimpse of OK Computer was this six-minute epic, a twisting, churning tribulation that essentially amounted to Radiohead’s own “A Day in the Life” “Paranoid Android” is a confoundingly brilliant piece, a four-part atlas of Thom Yorke’s naked, howling emotions, mutated guitar riffs, and quickly morphing dynamics, rarely held down by its weighty contents. From the song’s ease of change from rabid horror to pure ecstasy, or even Yorke equating modern yuppie culture to the crumbling Roman Empire, “Paranoid Android” is both a ferocious space-rock odyssey and a tantalizing promise of OK Computer’s—and Radiohead’s—imminent greatness. Liedel


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26. Beck, “Where It’s At”

“That was a good drum break” Yes, it was, and the horn break toward the end of the track deserves similar praise. The giddy “Where It’s At” was a useful lead single for Odelay because of its utterly harebrained composition, hinting at the album’s feral unpredictability while traversing sounds that became gradually more bizarre as the song nears its agitated conclusion. On numerous occasions throughout, Beck claims he’s armed merely with “two turntables and a microphone,” but that may just be one of the decade’s grossest understatements: This is a dizzying hodgepodge of multifarious sounds, a pounding headache of madcap styles, pinned together by peculiar samples and a buoyant organ hook. Jones


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25. Radiohead, “Karma Police”

Pinpointing the kernel of paranoia underlying Ok Computer’s existential dread, “Karma Police” imagines a world where everyone’s insides are laid bare, their souls ripe for criticism and judgment. Whether the karma police were agents of a dystopian future, a politically correct present, or some of Thom Yorke’s inner demons is impossible to say. It’s this kind of elusive ambiguity that makes the band’s declaration of millennial angst less a moldering artifact than an eerie document matching personal with public, one man’s internal fears dovetailing with the dominant concerns of a time. Cataldo


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24. Missy Elliott, “The Rain (Supa Dupa Fly)”

The Ann Peebles sample makes for a memorable hook, obviously, but what Missy proved on her first time out was that she able to do more with nothing than anybody else in the game. “The Rain (Supa Dupa Fly)” is barely a song, with little more than an otherworldly bassline to back the “I Can’t Stand the Rain” sample and Missy’s spare, juvenile rhymes. But damned if Missy can’t hold our attention. From the “Can we get freaky tonight” line that she unexpectedly sings in the opening verse to the is-she-serious-with-this-shit “Who got the keys to the jeep?” sound effects, she puts on one hell of a show. Nineties hip-hop was often defined by its excesses, but Missy’s brand of minimalism was no less of a spectacle. Keefe

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23. Massive Attack, “Unfinished Sympathy”

Massive Attack might be the quintessential trip-hop group, but I prefer to think of “Unfinished Sympathy” as metaphysical disco. Shara Nelson’s formidable wail punches right through the track’s gloomy snythscapes, and when she executes her most daring runs, her soprano seems to levitate miles above the grimy beats. At first, Nelson bares her broken heart like she’s Donna Summer or Gloria Gaynor, but her lament soon takes on creepier dimensions: “Like a soul without a mind/In a body without a heart/I’m missing every part” For the finale, the canned disco strings bloom into orchestral glory that their compressed MIDI counterparts suggest but never convey—fitting, as “Unfinished Sympathy” itself delves fearlessly into the raw emotional space that every disco torch song takes for granted but which even the best ones often reduce to kitsch. Cole


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22. Janet Jackson, “If”

If janet. found Miss Jackson asserting her right to have an orgasm the likes of which would dwarf your puny muscular spasms, the ruthless dance rock of “If” is the proof. Aided immeasurably by a Supremes sample filtered enough to suggest a cybernetic logjam, “If” ain’t no question mark. It prowls, marking its prey, staking its claim, going down-duh-down-down-down-duh-down-down on you while playing with your mind. More metallic than carnal, “If” really peaks when it reaches the sweet harmonies of the bridge before plunging headlong into the crunching paradox of the chorus. If she was your girl, she might treat you better than she claims. But you wouldn’t sweat half as much. Henderson


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21. Portishead, “Glory Box”

Second only to its flawless production, which includes a sample of Issac Hayes’s “Ike’s Rap II,” is Beth Gibbons’s impeccable lyrics and vocal performance on “Glory Box.” Her voice sounding like it’s coming out of an antique radio, she’s at once coquettish and despondent, like a lounge singer delivering her final torch song before slinking off to her dressing room to drown her sorrow in booze and heroin. Her voice blossoms with momentary optimism during the second verse (“A thousand flowers could bloom!”) and, of course, during the song’s rousing chorus: “Give me a reason to love you/Give me a reason to be a woman.” A post-feminist anthem from the hungry, seedy depths of lust. Cinquemani


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20. Weezer, “Say It Ain’t So”

For at least one track on The Blue Album, Weezer found soul, as the bluesy “Say It Ain’t So” channels the quartet’s nerdy agony into a slow-burning narrative on familial drama and unrequited anger. Yet despite the serious lyrical turn, Weezer sacrifices none of their singular quirks, as Rivers Cuomo essentially sings of beer-induced guilt while fueled by the band’s preferred strain of chunky loud-soft dynamics. Weezer is in perfect form here: Clean, almost jazzy guitar strikes greet listeners before pedaling into a wonderfully husky distortion, matching Cuomo’s wry visions with naked rock ‘n’ roll power. Liedel

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19. Aaliyah, “Are You that Somebody?”

What did they say when peanut butter first met jelly? On paper, the idea of an Aaliyah and Timbaland collaboration sounds like a match made in hell, but this seminal track of the ’90s stands as a triumph of rhythmic counterpointing. Timbaland’s chunky everything-but-the-kitchen-sink production would be a total earsore if it weren’t so gleefully goofy (its cooing baby anticipates the equally cartoonish laughing chorus of Justin Timberlake’s “My Love”), suggesting throughout as if it were in relentless pursuit of Aaliyah’s coyly smooth—deceptively detached—vocals. Theirs is a staggering back-and-forth, a hot-like-fire meeting of funky, beatboxing hip-hop and velveteen R&B. Gonzalez


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18. OutKast, “Rosa Parks”

How many hip-hop songs do you know that feature a totally straight-faced harmonica break? OutKast’s two MCs will play just about anything for laughs, but they’ve always been serious about their musical experiments, here making roots music and ATLien hip-hop sound as appealing a blend of Southern staples as whiskey and lemonade. Lyrically, the song straddles novelty and flat-out brilliance even tighter than “Hey Ya” Both André 3000 and Big Boi could lay claim to the title of hip-hop’s wickedest wits, and the basic lyrical conceit of “Rosa Parks” is in such audaciously poor taste that getting indignant and getting down seem like equally appropriate responses. And eclectic as their catalogue would become, OutKast never did another funk-country jam—fitting for a duo that tossed off new styles as readily as lesser MCs rattle off punchlines. Cole


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17. 2Pac f/ Dr. Dre, “California Love”

Thank Roger Troutman and the talk boxing he does on “California Love”—e.g., all of the lines about the various L.A. neighborhoods that know how to party—for the advent of Auto-Tune as a hook. The idea may have been novel at the time, sure, and there’s no way that Dr. Dre, in mixing “California Love,” could have predicted the likes of T-Pain and Ke$ha and how they would make Top 40 unlistenable. But the talk boxing effect on Troutman’s crooning is actually in service of the song’s production; it isn’t just an end unto itself. Floating atop one of Dre’s most aggressive beats, Troutman’s lines provide a proper setting for 2Pac’s and Dre’s traded verses. “California Love” may not be 2Pac’s deepest cut, but it finds two hip-hop giants near the absolute top of their games. Keefe


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16. Madonna, “Ray of Light”

Once the Material Girl made it her mission to bring electronica to the masses, she could have named her collaborator. Her decision to work with William Orbit shows that, for all the flack she’s faced for “appropriation,” her interest in underground dance music is deep and not wholly commercial. Madonna discovered techno just as she turned 40 and took up Kabbalah, and listening to “Ray of Light,” it’s easy to imagine Madonna finding in rave culture not just a new image, but a way of expressing her spiritual awakening. The beat is restless and Madonna sings breathlessly, but she exudes contentment: “I feel like I just got home!” Her emotional warmth is what establishes the song as a standout single even in a catalogue as replete with classics as Madonna’s. Cole

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15. BLACKstreet f/ Dr. Dre, “No Diggity”

I’ve had a few arguments with a close friend I consider to be something of an authority on ’90s R&B about whether or not BLACKstreet’s “No Diggity” is superior to Mark Morrison’s “Return of the Mack” in terms of combining straightforward R&B, new jack swing, and hip-hop. Her argument tends to boil down to a bias toward music from the U.K., where Morrison’s single was the bigger hit, while my position is to issue a challenge to think of another single that makes better use of its sample as a hook than does “No Diggity” That little half-hum, lifted from Bill Withers’s “Grandma’s Hands,” that runs through the song is simply the most voracious earworm of the ’90s. Keefe


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14. Dr. Dre, “Nuthin’ But a ‘G’ Thang”

It may have Dr. Dre’s name on the tin, but “Nuthin’ But a ‘G’ Thang” belongs to a young Snoop Doggy Dogg (he even takes the sole songwriting credit). The lazy keyboard line and warm, walking bassline are seemingly tailor-made for Snoop’s languid flow, the perfect arena for his queerly pitched self-appraisals. This single, more than any other of The Chronic’s big numbers, manages to effortlessly glide along that fine line between smooth and sleaze (in the wrong hands, it could quite easily have sounded like the backing track to a dodgy porno flick), and in doing so serves as the finest pointer to the G-Funk sound. Jones


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13. Beck, “Loser”

Upon its meteoric rise, “Loser” was labeled as the anthem of a generation, but the track always seemed to play as an outsider’s self-embrace of his estranged status away from any particular movement. Beck’s opening assertion (“In the time of chimpanzees, I was a monkey”) and his subsequent career diverging from the alterna-rock mainstream appears to confirm that suspicion, and to this day, the trippy “Loser”—steeped in ex-hippy folk counterculture and hip-hop experimentalism—remains the type of odd, genre-bending piece that would belong to a one-hit wonder destined to disappear into alterna-folk obscurity. Fortunately, it was simply Beck’s opening barrage in a strange, fruitful career of subverting musical norms. Liedel


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12. Smashing Pumpkins, “1979”

The song’s functional exploration of high school social mores may have seemed spot-on at the time of its release, but “1979” now functions as an exercise in reflexive nostalgia, casting a rosy sheen on the bitterness of teen angst. Many of the band’s songs effectively merged romance with sorrow, but none better than this one. Aided by its famously evocative video, “1979” will forever pluck the wistful chords of those longing to be young, anxious, and miserable once again, masterfully evoking a time when the world seemed huge and uniformly frustrating. Cataldo

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11. Deee-Lite, “Groove Is in the Heart”

When I forced my esteemed colleague Ed Gonzalez to listen to Betty Boo’s Boomania for consideration for the albums half of this feature, he likened it to sitting on a Whoopee cushion for half an hour. A ringing endorsement if I ever heard one, and it’s also an apt description of Deee-Lite’s “Groove Is in the Heart,” a sampladelic collage of breakbeats, cowbells, and, uh, the sounds of Eva Gabor getting goosed, all compiled from sources as disparate as the soundtrack to Blow-Up and an intructional belly-dancing record from the ’60s. The chill that’s spilled up your back? Yeah, that’s the slide whistle from Vernon Butch’s 1979 single “Get Up” The song is a world fusion of funk, house, soul, hip-hop, and salsa that only a trio comprised of a bell-bottomed club kid from the midwest, a vinyl-bin scavenger from Japan, and a house DJ from Kiev, Ukraine could concoct. Cinquemani


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10. Madonna, “Vogue”

Much has been written (specifically on this site) about the cultural impact of the appropriation of queer and nonwhite motifs in Madonna’s “Vogue,” so I’ll focus instead on the song’s musical archaeology and influence. Lest I completely ignore its substance, Madonna’s message is clear (“Beauty is where you find it”), but the track’s origins are part and parcel with its star’s mining of gay club trends and Old Hollywood: Inspired by the Salsoul Orchestra’s “Ooh, I Love It (Love Break)” by way of Danny Krivit’s remix of MFSB’s “Love Is the Message,” the song has a family tree that even includes producer/DJ Shep Pettibone’s remix of Janet Jackson’s “Miss You Much” and serves as a sort of musical map of disco. Pettibone recorded “Vogue” with Madonna as a B-side for her single “Keep It Together,” making its impact all the more impressive (it would go on to inspire a glut of pop-house copycats) and begging the question: If disco died a decade earlier, what the fuck was this big, gay, fuchsia drag-queen boa of a dance song sitting on top of the charts for a month for? Cinquemani


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9. Björk, “Hyperballad”

In “Hyperballad,” Björk confesses to a puzzling ritual: She rises each morning to indulge her destructive side, tossing household items off a cliff and observing their plummet before returning to the comfort of her lover. She imagines herself taking the big dive too, but never actually jumps. After all, as she assures over the song’s perfect club chorus, she’s doing this for us. Björk’s lyrical Rubik’s Cube is endlessly interpretable, but however powerfully it insists on the tension between love and individuality, its composition is all Romantic reconciliation. Björk’s cosmopolitan pop sensibility makes room for disco, baroque pop, and acid house, while her singular voice eventually dissolves into the song’s grandiose strings. If she senses something tragic in the desire to lose oneself completely to love, she apparently detects no such danger in surrendering, at least momentarily, to music. Cole


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8. The Breeders, “Cannonball”

The legend goes that Kim Deal was denied much creative input with the Pixies, and the resulting fracas with the band’s frontman Black Francis eventually lead to the group’s demise in early 1993. When listening to “Cannonball,” the lead single from the platinum-selling Last Splash, it’s difficult to understand why Ms. Deal wasn’t allowed to spread her creative wings with the Pixies. The song is blessed with a clutch of feverish hooks, gradually building in tempo to a frantic refrain at the death. And that bassline is surely one of the best of the decade, simple but endlessly effective. “Cannonball” proved that Deal was more than worth her salt as a songwriter, delivering an album’s worth of zinging melodies with this one track alone. Jones

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7. Beastie Boys, “Sabotage”

Who would’ve thunk that the decade’s hardest rocking shot of electric guitar testosterone this side of the stupid and the contagious would come from the trio of scrawny boy-punks who made their name with the Casio krush grooves “Brass Monkey” and “Girls”? The Beastie Boys’s “Sabotage” brushes past the cheap novelty of Aerosmith crashing Run DMC’s party, borrows a little bit of Anthrax from Public Enemy, and, to put it bluntly, throws a dump truck through the picture window of Sal’s Famous Pizzeria. (The accompanying Spike Jonze video, in which Ad-Rock, Mike D, and MCA careen through a 1970s cop drama, would be an even bigger classic if its interpretation of the song’s octane rating weren’t just a tad too on the nose.) Henderson


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6. Lauryn Hill, “Doo-Wop (That Thing)”

The Miseducation of Lauryn Hill wasn’t designed as a crossover record, but with “Doo-Wop (That Thing),” her conquest of the pop charts and the Grammys was effectively guaranteed. And “Doo-Wop” isn’t just her best single; it’s the definitive snapshot of the Lauryn Hill persona, capturing a poised and candid truth-teller in her hip-shaking, finger-wagging prime just before she disappeared into her own ego and then, literally, disappeared. But she performs her breakthrough single with such purpose that even her less ingratiating traits seem vital, minimizing neither the street in her wisdom nor the self in her righteousness. Sometimes a sister’s got to preach, and Hill’s equal-opportunity call-out on two-timers made for her most resonant sermon: Where her political slogans often dated themselves, Hill’s message in “Doo-Wop”—that there are finer things than fine booty (among them, integrity)—will never want for relevance. Cole


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5. Nine Ninch Nails, “Closer”

If the truly maladaptive take pleasure in their corruption, then Nine Inch Nails’s “Closer” is the Who’s Afraid of Virginia Fucking Woolf of industrial rock. It’s certainly the most persuasively seductive effort to ever flow from Trent Reznor’s pretty hate lips. With effortless grace, he moves from insisting “I’ve got no soul to sell” to promising “I want to fuck you like an animal” And just as the deal has been sealed by producer Flood’s heady synth-pop approximation of the sound of a headboard banging away inside a torture chamber, he profanes the entire indecent proposal with a discursively profane “You get me closer to God” Good sex never sounded so bad, but a word of advice: Gag Reznor with a rubber ball after he comes. You don’t want this brand of post-coital chatter. Henderson


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4. The Verve, “Bittersweet Symphony”

Me on the video for the Verve’s “Bittersweet Symphony”: “Life sucks, especially when the government milks you dry and doesn’t so much as give you a wider sidewalk for your troubles” This gorgeously anthemic song is a requiem for a jilted generation, and given the state of the economy these days, it resonates more than ever. And that’s nothing to say of the bittersweet irony of the Verve losing ownership of the song. The simple lyrics, now shamelessly credited to Mick Jagger and Keith Richards, are about frustration and desperation, and Richard Ashcroft’s vocal performance coasts above the symphony of strings with a soulful detachment. He’s grandiose because he’s talking about life—not just his, but all of ours. Gonzalez

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3. R.E.M., “Losing My Religion”

We’ve all gotten to the point that we agree that “Losing My Religion” isn’t actually about religion, right? The phrase itself is a terrific, versatile bit of Southern vernacular that can add color to even the most ho-hum, familiar stories, and that’s precisely how Michael Stipe uses it on R.E.M.’s most enduring single. That ominous little mandolin figure that drives the single gives real gravity to Stipe’s free-form images about wanting to give into—to really just commit without reservation or thought, which is the gist of the idiom—a hopeless romantic crush even when crippled by the possibility of rejection and humiliation that crush might bring. Keefe


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2. Sinéad O’Connor, “Nothing Compares 2 U”

Nothing compares to this song, in which pop music’s most emotion-rich voice sings words by pop music’s most emotion-rich lyricist. Similar such meetings of titans have resulted in disasters before, solipsistic earsores mostly, but Sinéad O’Connor—like she would do some time later with Nirvana’s “All Apologies”—doesn’t treat “Nothing Compares 2 U” as if it were a cover. She performs Prince’s lyrics as if the emotions inscribed in them were her own, and the proof is in her hauntingly aching belting. The experience is, like that tear that streaks O’Connor’s face in the song’s video (a response, the singer has claimed, to the line “All the flowers that you planted, Mama/In the back yard/All died when you went away”), practically holy. Gonzalez


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1. Nirvana, “Smells Like Teen Spirit”

For a song that has long been championed as the theme of a specific crowd of slacker youth, “Smells Like Teen Spirit” endures beyond the ownership of any one subgroup. Kurt Cobain’s self-admitted attempt at a pop song achieved many things (helping to bring grunge from the sweaty depths of the mosh pit to the radio-friendly mainstream, launching Nirvana into Gen-X superstardom, and so on), but perhaps most importantly, it set the tone for all alternative music that followed. Its stuttering riff line instantly recognizable, “Smells Like Teen Spirit” is akin to Chuck Berry’s “Johnny B. Goode” in raw industry impact, pushing not just the rock genre, but the entire music world forward. “Here we are now,” Cobain announces, “entertain us!” Liedel

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