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
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
99. Stardust, "Music Sounds Better 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." EH
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
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
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
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
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
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. HJ
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. SC
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. JK