The 25 Greatest Breakup Songs of the 2000s

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The 25 Greatest Breakup Songs of the 2000s

Cry us a river.

We recently assembled the greatest love songs of all time, but let's face it: while love has inspired some great songs, the majority of classics come from a darker place. Our rules this time were simple: a breakup song can be vengeful, dignified, devastated, or whatever else, as long as the lyrics make explicit reference to a relationship that is ending or has ended. Again, we limited it to one song per songwriter (not necessarily per band). Come back next week for the best breakup songs of the '00s, and let us know what we missed in the comments. Also, feel better. You're going to get through this, and to help with that, here's a Spotify playlist of this week's list, and here are the greatest breakup songs of the '60s, the '70s, the '80s, and the '90s. — The Hooksexup Editors

25. Lady Gaga, "Eh, Eh (Nothing Else I Can Say)" (2009)

While most of Gaga's tracks are about a romance she knows will eventually go bad, this early tune is about actually breaking up. What makes "Eh, Eh" great is its appropriation of bubblegum pop to say something decidedly un-sweet. Plus, the song's hilarious music video set the tone for what was to follow: our romance with Gaga would be anything but boring. — Rachel Krantz


24. Arcade Fire, "Crown of Love" (2004)

"Crown of Love" is for everyone who's simply fell out of love. It captures the contradictory realities of indifference and volatile emotion. "If you still want me, please forgive me" is all you can say to someone when you've moved on before they have. — Jeremy Glass


23. Coldplay, "The Scientist" (2003)

I'm not made of stone. I don't like Coldplay, but I have a particular weakness for piano-driven ballads, and who among us can't identify with "take me back to the start?" Besides, no less an authority on heartbreak than Willie Nelson has covered "The Scientist," so there's that. Anyway, go ahead and play it a couple of times. I won't tell anyone. — Alex Heigl


22. The Killers, "Mr. Brightside" (2004)

Jealousy and infidelity are the death row and lethal injection of every relationship, respectively — and "Mr. Brightside" reminds you to move on ASAP when you get cheated on. According to Brandon Flowers, "Mr. Brightside" is a true story; when paired with a hot riff, that story reminds us that anger, envy, and sadness can actually be danced away. — J.G.


21. LCD Soundsystem, "Someone Great" (2007)

The meaning of this particular breakup song has been under debate for while. Maybe the "someone" is a guy's new lover, maybe it's the old lover who's been left behind, and maybe it's about a failed pregnancy. Regardless of the song's subject, when someone great leaves your life, you'll find yourself surprised by the weird things you miss about them. — J.G.


20. Lily Allen, "Smile" (2006)

Finally, a breakup song that doesn't incite days of sobbing in the fetal position. There's no beating around the bush with this one: "When I see you cry, it makes me smile." "Smile" is about relishing your ex's sadness. Is it all right to enjoy a song that celebrates the misery of others? Fuck diplomacy, right? — J.G.


19. Ryan Adams, "Call Me On Your Way Back Home" (2000)

Not surprisingly, Ryan Adams' dusty masterpiece Heartbreaker is primarily concerned with heartbreak (and arguing about Morrissey songs). That "Call Me On Your Way Back Home" stands out in such a stacked deck is a triumph. The bluesy turns in Adams' vocal and his barely-there guitar work slowly build until the song's last line, "I just wanna die without you," which is almost too maudlin for Adams to sell. Almost. — A.H.


18. Kanye West, "Heartless" (2008)

Per the leader of the free world, Kanye is a jackass, but talented. Who better to write about lost love than a talented jackass? And who said an Autotuned ballad couldn't have heart? Autotune is actually a pretty clever way to capture the detachment and falseness one feels with heartbreak. Nice work, jackass! — Sean Morrow


17. Grizzly Bear, "Knife" (2006)

"Knife" sounds like pulling yourself out of a bad breakup feels. It's a murky, impenetrable haze of harmonies and accusatory lyrics, and it sounds like it's being broadcast from the bottom of a very dark cave. Even the weird jumble of sounds that serves as the song's outro mirrors the breakup experience — it's the sound of someone trying to pull their thoughts together before inexorably coming back to one motif: "You think it's all right?" — A.H.


16. Aaliyah, "Miss You" (2001)

Though it's taken on a far more poignant meaning in the wake of the singer's death, Aaliyah's "Miss You" is, at its heart, a breakup song. And a sweet, sincere one, at that. Aaliyah's singing voice always had a vaguely detached quality, and, when backed by Timbaland's Nine-Inch-Nails-by-way-of-the-hood beats, she could come off as remote or dispassionate. That's not the case here — this song is all heart, and all heartbreak. — XX


15. Bright Eyes, "Land Locked Blues" (2005)

Conor Oberst might have the voice of an petulant kitten, but he knows his way around a set of lyrics. "Land Locked Blues" is an existential crisis filmed through the lens of a relationship, and Oberst's lyrics, pulling the rare trick of being specific and universal, gain extra force from guest vocals by Emmylou Harris, who sounds like a full-grown cat. — A.H.


14. Feist, "Let It Die" (2004)

"Let It Die" lands somewhere between melancholic and out-and-out heartbreaking, like Feist's voice itself. But this track isn't just beautifully sung — it's beautifully written. With lines like "The saddest part of a broken heart/Isn't the ending so much as the start," this song captures the pain of letting go of your hopes. — R.K.


13. Black Keys, "10 A.M. Automatic" (2004)

You can't really talk about the aughts (is that what we're calling them?) without talking about The Black Keys. They helped revive garage rock (again) and gave us gritty-but-accessible songs like "10 A.M. Automatic." This breakup song is all about a Jekyll/Hyde situation, where someone you date seems to have two faces. Listen to this one when you just can't take their drunk face anymore. — R.K.


12. Bon Iver, "Skinny Love"

If you're trying to make haunting breakup music, heading into exile in the woods of Wisconsin is almost cheating. But the results speak for themselves. This is heartache on a different level; sadness for the one who left and remorse for the person you've become. — J.G.


11. Beyonce, "Irreplaceable" (2006)

The best thing about "Irreplaceable," other than the usefulness of "to the left, to the left" in everyday conversation, is the surprise revelation in the second verse: "Oops, I bet you thought that I didn't know/What did you think I was putting you out for?" Upon discovering her boyfriend's unfaithfulness, Beyonce doesn't fall apart or even get angry. There's no confrontation, no discussion, no argument. Instead she coolly reveals to him what she knows, and introduces her new man in the same move. It's textbook Beyoncé: classy, empowered, and possessed of a wicked sense of humor. — Natasha Ochshorn


10. The Walkmen, "The Rat" (2004)

To really understand this song, you need to watch a live version and see how furiously guitarist Paul Maroon strums the intro. Then Matt Barrick starts beating his drums like they killed his dad, and one of the most righteously pissed-off breakup songs of the decade is off to the races. It's a gloriously spiteful kiss-off, and one perfect for pounding the pavement after a breakup. — A.H.


9. Kelly Clarkson, "Since U Been Gone" (2004)

Obnoxious text-speak aside, this is how you build a pop song. Clarkson's voice starts out low, the drums sound like a Casio keyboard, and you're wondering what's so great about this club and why you've been dragged here when you just want to sulk at home. Then that chorus decks you in the face, and before you know it, you've had four shots because you're so fucking fierce and you don't need him (or her), you don't need anyone and you're jumping around like an idiot… and here comes that chorus again! — A.H.


8. Macy Gray, "I Try" (2000)

Though she was unable to capitalize on it, Macy Gray will always be remembered for this perfect pop gem. Her odd vocal affectations (exactly what accent is that, again?) bump up against her band's joyously swinging performance, and by the end of the song, you're less aware of her voice's gravelly timbre than with its exuberance — she's made heartbreak sound like a party. — A.H.


7. Rilo Kiley, "More Adventurous" (2004)

"With every broken heart, we should become more adventurous." Go through a lot of lousy shit, and you might end up rewarded with a kind of weary grace. That's the place Jenny Lewis sings from in "More Adventurous," the prettiest song on the mostly overworked album of the same name; she's lost a lot of love, but she still has enough to get by. — Peter Smith


6. Beck, "Guess I'm Doing Fine" (2002)

Sea Change must've come at a hard time in Beck's life — it's pretty much all breakup songs, many of them beautiful. Like "Nothing Compares 2 U," "Guess I'm Doing Fine" covers a biting breakup paradox: you're still alive, you have all your limbs, you can do whatever you want, but none of it feels very good. — S.M.


5. Wilco, "I Am Trying to Break Your Heart" (2002)

Jeff Tweedy often seems to be trying to obscure his emotional songwriting with avant-garde touches like weird ambient sounds, deliberately "wrong-sounding" notes, and obtuse lyrics. But none of those elements can stop "I Am Trying to Break Your Heart" from succeeding in its titular aims. — A.H.


4. The Strokes, "Someday" (2001)

Equal parts regret and boozy barstool philosophy, "Someday" is a broadly focused portrait of a breakup. Though the line "alone we stand, together we fall apart" hints at a relationship dissolved for its own good, the song is as much about letting go of youth as it is about letting go of someone, and Julian Casablancas' disaffected croon obscures some of his most painfully sincere lyrics. — A.H.


3. Justin Timberlake, "Cry Me A River" (2002)

Who ever would've thought that the dopey fresh-faced bleach-blonde kid from 'NSYNC would grow up to have this much soul? If JT wants me to cry, damn it, I'm cryin'. — J.G.


2. Amy Winehouse, "Tears Dry On Their Own"

The juxtaposition of the music from Marvin Gaye and Tammi Terrell's classic "Ain't No Mountain High Enough" and Winehouse's self-penned lyrics and melody is the first thing you're likely to notice about this song. But last year's Lioness: Hidden Treasures revealed the original version of "Tears," and shockingly, it didn't matter that much — Winehouse's desperate, lonely vocal was just as evocative and touching as ever, proving that no matter how many people accused her of slavish pastiche, Winehouse's voice was always her own. — A.H.


1. Outkast, "Ms. Jackson"

This is probably the only breakup song ever addressed to the singer's mother-in-law, but the gambit pays off. By directing his imploring lines to Erykah Badu's mom instead of Badu herself, Andre 3000 makes an implicit statement about how the idealism of young love ("that crib with the Goodyear swing") gives way to the complexities of adulthood: private schools, day care, lawyers. Mothers-in-law. It's rueful, but it's loving too. — P.S.


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