100 Best Songs of the ’00s (#40-31)

These are the best songs of the 2000s.

35: Bon Iver – Skinny Love (2007)

Justin Vernon’s group became indie darlings on the heels of this, the first single from the self-released debut, For Emma, Forever Ago, which was recorded in the solitude of his father’s hunting cabin in Eau Claire, Wisconsin. Independent label Jagjaguwar picked up the record and released it the following year. With only the strum of an acoustic guitar to introduce him, Vernon sings in his experimental falsetto and subtle echo, “Come on, skinny love, just last the year.”

Many fans and critics think Vernon is singing about ex-girlfriend Christy Smith. In a 2011 interview with Pitchfork, the songwriter claimed that “would not be entirely accurate,” and explained that the title refers to being, “in a relationship because you need help, but that’s not necessarily why you should be in a relationship. And that’s skinny. It doesn’t have weight. Skinny love doesn’t have a chance because it’s not nourished.”

No matter its true subject, “Skinny Love” is an enduring, intricate and distinctly-told tale of heartbreak. It’s sung by a man who feels he is in a hopeless relationship, begging his partner to end it because he is too cowardly to break it off himself, begging, “I tell my love to wreck it all/ Cut out all the ropes and let me fall.” Intensity and volume increases as it progresses; following the first verse, percussive elements are slowly added and Vernon’s tone becomes more urgent. In the first chorus he admits his faults and what he owes to his partner: “And I’ll be holding all the tickets/ And you’ll be owing all the fines.” Yet in the angry final chorus he confronts the way his lover dealt with the end of the relationship: “And now all your love is wasted/ And then who the hell was,” finally asking, “Who will love you?/ Who will fight?/ Who will fall far behind?

“Skinny Love” was the kind of defining breakup song that had eluded indie rock in the ’00s, confronting typical and sometimes clichéd stories of heartbreak, lost love and the fear of one’s own insignificance. It’s the kind of song that could only have come from Justin Vernon. – Natalia Barr

34. Jay-Z – Big Pimpin’ (2000)

Although the album Vol. 3… Life and Times of S. Carter emerged four days before the new millennium, its most popular and commercially successful song was released as the album’s fifth single in early 2000. For this bumping ode to pimp life, the self-proclaimed king of New York rap bridged the regional divides that characterized ‘90s and early ‘00s hip-hop by collaborating with Houston rap impresarios UGK. Inspired by the Pretty Tony character from the 1973 film The Mack, Jay-Z is at his most boastful and unaffected here, dishing up the ultimate playa anthem about the champagne-popping lifestyle of a pimp.

Despite virtuosic flows from hip-hop royalty, the highlight of “Big Pimpin’” is producer Timbaland’s Middle Eastern-influenced beat, which was unlike anything else in hip-hop at the time. Flamboyant and exuberant, the beat shimmies with an Egyptian flavor and was made all the more opulent by Hype Williams’s music video shot on a lavish yacht during the Trinidadian Carnival. The beat provides the perfect backdrop for a song that champions luxury and excess. As infectious as it was, it caused controversy, as Jay-Z and Timbaland were sued for using samples of “Khosara Khosara” by Abdel Halim Hafez.

Over this exotic rhythm, Jay-Z and UGK’s Pimp C and Bun B deliver the beats, hooks and braggadocious rhymes representative of East Coast and Third Coast’s finest. However, Jay-Z has since admitted shame for the crude verse: “I thug ‘em, fuck’em, love ‘em, leave ‘em/ Cause I don’t fuckin’ need ‘em.” But despite their misogynist character, the lyrics reveal something more vulnerable: “Me give my heart to a woman?/ Not for nothing, never happen—I’ll be forever mackin’/ Heart cold as assassins, I got no passion, I got no patience.” Jay-Z acknowledges that he is unable to love or even feel anything at all, his pimp persona a cover for lack of emotional aptitude on a spirited mixture of world music, East Coast hip-hop, and Southern rap. — Ethan King

33: Kelly Clarkson – Since U Been Gone (2004)

Bitterness and triumph are an odd pair, but probably less so when you have Max Martin and Dr. Luke working together. Add Kelly Clarkson, one of the best vocalists of this century, and you get one of the very few perfect pop songs of the ’00s.

Taken as the lead single from Clarkson’s finest record, Breakaway, “Since U Been Gone” is perhaps the decade’s most anthemic kiss-off. The singer sees 20/20 as she reflects on a friendship that turned romantic: “We started out friends/ It was cool, but it was all pretend”. She has strong feelings: “And all you’d ever hear me say/ Is how I picture me with you”; unfortunately, they are not reciprocated: “How come I’ve never heard you say/ ‘I just want to be with you?’/ Guess you never felt that way.”

In fact, she may have been manipulated. “How can I put it? You put me on/ I even fell for that stupid love song.” This bloodletting leads to (and justifies) that supernova explosion of a chorus that delivers an impossible catharsis. Clarkson’s performance shifts from the matter-of-fact verses to the Herculean hook. When she proclaims, “But since you been gone/ I can breathe for the first time” you’re certain she’s telling the truth. She even offers some acerbic gratitude to her ex: “Thanks to you, now I get what I want.”

Neither Martin nor Luke have done much in the way of rock, but when they have (as on Bon Jovi’s “It’s My Life” and Daughtry’s “Feels Like Tonight”), the results were fantastic pop-rock. Their Clarkson hit was so successful that the duo teamed up again a year and a half later with P!nk for the near-rewrite “Who Knew. “But Alecia Moore isn’t the singer that Clarkson is, and therein lies the key to the song’s true greatness. Martin and Luke have written many superb pop songs for many different artists, but there’s only one Kelly Clarkson. – Steve Lampiris

32: The Flaming Lips — Fight Test (2002)

The opening track to the band’s mainstream breakout Yoshimi Battles the Pink Robots, this worthy successor to “Race for the Prize” owes some of its musical DNA to Cat Stevens’s “Father and Son”—so much so that Stevens, now Yusuf Islam, gets 75 percent of the song’s royalties.

“Fight Test” is built on Steven Drozd’s unmistakable, syncopated drums filtered through Dave Fridmann’s signature production along with plump, bouncing keyboards and shimmering chords. It doesn’t have the same drive as “Race,” but rather a loping, wistful feel, less competition than contemplation and self-reflection.

I thought I was wrong/ Thought I was right/ I thought it better not to fight/ I thought there was a virtue in always being cool.” This relatable virtue has been used as the theme for an MTV cartoon and turned up on TV in “Smallville.” This is not your average indie song. As suits its later use, lyrics could refer to something small-scale (a schoolyard brawl or romantic rivalry) or large-scale (world war or species-wide strife). The refrain, “I don’t know where the sunbeams end and the star lights begin/ It’s all a mystery” is pure Lips, choosing the wisdom of uncertainty over any fixed interpretation.

“Fight Test” begins Yoshimi’s conceptual narrative, but in a sense Wayne Coyne follows in the footsteps of “Father and Son,” its two figures coexisting in a single entity, reflecting on its maturity and deciding what kind of creature it wants to be. While most fans think of the more Hallmark-ready “Do You Realize?” as the Lips’ most universal paean, this is a high-water mark in the band’s catalog, a folk tune in a millennial’s clothing, at once utterly new and irresistibly retro, a future past for precocious nostalgics. Echoing its lyric, Coyne told The Guardian, referring to the Cat Stevens brouhaha, “I really apologize for the whole thing.” However derivative it may have been, the song is apology enough. – Dylan Montanari

31. Britney Spears – Toxic (2003)

If it weren’t for the singer’s own intervention, this might have been an avant-garde curio beloved only by hardcore fans. Originally offered to Kylie Minogue for Body Language, a puckishly experimental album that would have been a fantastic fit, “Toxic” was unceremoniously offered to Spears for In the Zone and not given much thought. When it came time for her to pick the album’s second single, she was given two options, both of which she declined in favor of a song that she still claims is her favorite of all her recordings.

Surprise: It turned out to be not only a megahit but one of the most respected pure pop songs of the last 25 years. “Toxic” landed on nearly every end-of-decade list, won Spears her first and only Grammy and gave Bloodshy & Avant, the two woolly Swedes behind the boards, an opening to dominate the indie-pop trend with their band Miike Snow. In poptimist circles, it’s taken on the stature of “A Day in the Life.” Even “Irreplaceable” and “Call Me Maybe,” which the most scowling rockists can’t deny, will usually be greeted at parties with joking sing-a-longs. Play “Toxic” and people go silent. Their eyes widen; they know they can’t compete.

There are better examples of how the pop landscape of the ‘00s was fertile for just this kind of experimentation, such as Justin Timberlake’s “Cry Me a River” or Snoop Dogg’s “Drop it Like it’s Hot. “ And to be honest, Bloodshy & Avant don’t do anything Timbaland didn’t do first. But “Toxic” shoves its eccentricities in the listener’s face—its bhangra samples, its weird backwards time-warps, its unstable start-and-stop. It doesn’t sound like many other pop songs, it knows it, and it wants everyone else to know it. It hits us as “weird.” Then it hits us on a deeper level, and we dance. — Daniel Bromfield

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