100 Best Songs of the ’00s (#90-81)

These are the best songs of the 2000s.

85: Kanye West – Gold Digger (2005)

(2005)There are two kinds of people: those who like “Gold Digger” and those who pretend not to.

Long before we started worrying and learned to hate Kanye, he was the absurdly talented art-school dropout who produced some of the best tracks on Jay-Z’s The Blueprint and delivered an all-time classic with The College Dropout, his debut album. When it came time for Late Registration, Kanye enlisted the assistance of Jon Brion (he admired his work on Fiona Apple’s albums), and the rest is history.

“Gold Digger” is not necessarily the best song on the album, but it is the most quintessentially “Kanye” song on the album—provocative, tongue-in-cheek and fun. Driven by Jamie Foxx’s uncanny mimicry of Ray Charles’s “I Got a Woman,” the song tells the story of a man beset by a female partner hungry for money. Kanye is no feminist, but it doesn’t take much imagination to see that the male protagonist gets ridiculed as much as anyone else. The reversal in the third verse at least suggests that the “gold digger” persona is highly dependent on and responsive to men whose sole source of self-worth is their wallet.

Beyond whatever message it might have, however, the song is a blast and funny as hell. It name-drops everyone from Serena to Trina to J-Lo, not to mention Busta and Usher. There is, naturally, a reference to Michael Jackson—only the second-best Michael reference in Kanye’s oeuvre—but the “We want prenup! We want prenup!” chant takes the cake. It’s hard to imagine Kanye making a song so lighthearted and joyful now (even the lighter moments of The Life of Pablo still had a sense of menace). While it’s impressive that Kanye has challenged himself (and us) as much as he has, we’ll always have “Gold Digger” to sing along to. “She take my mo-NEY…– Dylan Montanari

84: Fall Out Boy – Sugar, We’re Goin Down

Once you hear Andy Hurley’s pounding drums and Patrick Stump and Joe Trohman’s power chord liftoffs, there’s a good chance you’ll be singing at the top of your lungs, “Am I more than you bargained for yet?” So begins “Sugar, We’re Goin Down,” the 2005 breakout hit that not only propelled Fall Out Boy to superstardom, but also brought pop-punk-inspired emo into the mainstream. Released as the band’s lead single for their second album, From Under the Cork Tree, “Sugar” quickly became an emo anthem for the Myspace generation, rising all the way to number eight on the Billboard charts.

Although the song’s intro bears an uncanny resemblance to the beginning of Creed’s “Higher,” what many skinny-jean-clad teen fans glommed onto were Stump’s vocal hooks and the song’s quirky lyrics. The melodies are pure pop, but Stump’s voice possesses a unique on-the-verge-of-trembling quality matched only by Brendon Urie of Panic! at the Disco. Penned by bassist Pete Wentz, the lyrics are built on short and nearly incomprehensible phrases such as “I’ll be your number one with a bullet/ A loaded god complex, cock it and pull it.” But lines like “Watching you two from the closet/ Wishing to be the friction in your jeans” get at that angst-ridden mixture of jealousy and desire that the band’s young fans could relate to. Each phrase was unique and took on greater resonance with each play.

After “Sugar,” From Under the Cork Tree’s second single, “Dance, Dance,” propelled them even further, and in the wake of the band’s multiplatinum success, Wentz became the most publicly visible member of the band, assuming a celebrity status typically reserved for frontmen. Over a decade later, the band is still selling out stadiums and churning out successful records, but none of that would have been possible without the initial success of “Sugar, We’re Goin Down.” – Ethan King

83: Hot Chip – Boy from School (2006)

Hot Chip’s sophomore album, The Warning, was a solid leap forward. Previously, the band seemed content to take the piss out of dance music with their old synths and cheeky lyrics about Kraft dinners and blasting Yo La Tengo out the windows of their Peugeot. Hot Chip has always run the risk of letting this cheekiness get the best of them, their desire to let everyone know that they’re in on the joke overriding the real poignancy they seem to be able to summon at will. “Boy from School” is one of those magic moments where Hot Chip let their filter fall away, and they fill a dance-floor banger with unabashed emotion. Over propulsive drums and a nervous keyboard riff, Alexis Taylor and Joe Goddard croon wistfully about the loss of innocence suffered by every adult who’s ever had the temerity to grow up.

In true Hot Chip fashion, the band takes the idea of dance music and flips it around. If the dance floor is supposed to wipe away the troubles of your day-to-day existence, “Boy from School” forces you to wallow in the feeling of a life misspent. For Hot Chip, the greatest losses often come from just living your life; we all grow up, some faster than others, and there’s nothing you can do about it. The conundrum of thinking about the past and how everything changes is that it isn’t necessarily a bad feeling; nostalgia is an attractive endeavor even when it’s bittersweet. The deftly bifurcated vocals—Taylor on top, Goddard on bottom—embody that internal conflict. By the time the chorus hits, the song tries it’s best to comfort. Numerous voices join in to remind us, “We try but we don’t have long.” It’s cold comfort, but it’s something—a reminder that we’re all out there trying our best to figure everything out. – Eric Mellor

82: Jens Lekman – Black Cab (2004)

Jens Lekman spent the first decade of the new millennium in a wild burst of creativity that only seemed to lack direction. Over the course of all of his 2000s work, his most cohesive release was 2005’s Oh You’re So Silent Jens, a compilation of singles and EPs released over the course of a few years. Everything that makes Lekman a unique talent—particularly his acerbic wit and his knack for spinning melodic gold out of schmaltz—is on full display there, and it’s hard to pick a single standout moment. However, there’s just something perfect and complete about “Black Cab.” Of all Lekman’s songs, it’s the least playful and most acidic in the tone of its lyrics. Yet, its arrangement is a wondrous combination of the simple and the ornate.

It’s easy to draw comparisons to Stephin Merritt when listening to “Black Cab,” and, in fairness, Lekman’s low tone and meticulous arrangement here bears quite the resemblance to the Magnetic Fields frontman. However, Lekman is a master of character study and storytelling in a way that Merritt won’t allow himself to be. Here, Lekman plays the part of a regret-filled, socially-awkward version of himself, commuting home after an evening of failed social interaction. His lyrics and vocal performance do little to mask his bitterness; the bridge of the song has him snapping at his cab driver to stop asking him questions. It should be a darker song than it is, but its mix of live instruments and samples elevate it to an even higher level. The song sounds as light as one would expect from something that samples both Belle and Sebastian and the Left Banke, but there’s a sneakily slight amount of acid to go with the sugar, which is an incredibly difficult balance to maintain. Here, Lekman just about masters it. – Kevin Korber

81: The Postal Service – Such Great Heights (2003)

What started as a brief collaboration with Ben Gibbard on“(This Is) The Dream of Evan and Chan” from Dntel’s Life Is Full of Possibilities grew into a side project that would produce the Postal Service. With 10 songs that provided a soundtrack to the lives of lovelorn listeners, it’s no wonder the band’s sole album, Give Up, was Sub Pop’s first platinum record since Nirvana’s Bleach.

Give Up’s first single, “Such Great Heights,” is a song about love and distance, and the ways our brains help us cope with that distance, which fits well with the tape-trading-by-mail nature of the band. Leave it to Gibbard to write a song that so deftly utilizes tired Hallmark sentimentality while poking at silliness of those very sentiments. Nesting atop the sublime, sweet-but-never-saccharine beats of Dntel producer Jimmy Tamborello, Gibbard delivers two stanzas about the freckles in our eyes and compares himself and his lover to puzzle pieces, before verbally throwing these love notes into the garbage: “And true, it may seem like a stretch/ But it’s thoughts like this that catch/ My troubled head when you’re away/ When I am missing you to death.”

Addressing the underlying cause of those sappy feelings helps us pull back the veil on what makes a love song great in the first place, and Gibbard has always been self-aware enough to pull off that tightrope act. After fending off a chorus of naysayers begging him to “come down now,” he’s ready to pick it all apart even more. In listening to his own words on an answering-machine message, he discovers it sounds “thin,” which “will not fly.” He doesn’t really need those tired lines, anyway.

We’re nearly 15 years removed from Give Up and “Such Great Heights,” far enough that—for better or worse—many a bedroom producer since has tried to grab at what that band did there. The Postal Service will probably never make another record, and that’s okay. Gibbard created what he wanted: a song for us to stumble upon on the radio, with our car windows down, to guide us home. – Hollister Dixon

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