The 50 best breakup songs

Heaven knows you’re miserable now—so you may as well enjoy it with the best breakup songs ever made



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“Breaking up is hard to do,” sang Neil Sedaka in 1962, in a piece of chirpy understatement that’s on a par with Sir Cosmo Duff Gordon’s 1912 assessment of the Titanic sinking being “a rather serious evening.” Yes, breaking up is hard to do—so hard, in fact, that most of the best pop music ever produced has sprung from its well of agony. But as tough as it is to dump or be dumped, when you find the right soundtrack to your suffering, it can also feel weirdly enjoyable—as tracks by such pop poets as Alanis Morissette, Kanye and, of course, expletive king, Cee Lo Green attest. So we invite you to celebrate the heartbreak—whether angry, homicidal or just a bit sad—with our collection of the best breakup songs ever recorded. Hurts so good, don’t it?

Written by Michael Chen, Brent DiCrescenzo, Jonny Ensall, Adam Feldman, Sophie Harris, Oliver Keens, Tim Lowery, James Manning, Amy Plitt, Jenna Scherer, Hank Shteamer, Bruce Tantum, Kate Wertheimer and Kristen Zwicker.

Need a lift? Check out our list of the best love songs ever made

“Somebody That I Used to Know” by Gotye featuring Kimbra (2011)

“Somebody That I Used to Know” by Gotye featuring Kimbra

Wouter De Backer, a.k.a. Gotye, didn’t have a duet in mind when he first put pen to paper for “Somebody That I Used to Know,” but when he reached the end of the first verse, he knew it needed a little something more. Along came fast-rising New Zealand singer-songwriter Kimbra, whose impassioned delivery bolstered the tune with a new, fiery perspective. The result was a wildly successful crossover hit, which topped the charts in 18 countries and took home Record of the Year at the 2013 Grammys.—Kristen Zwicker

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“Fuck It (I Don't Want You Back)” by Eamon (2003)

“Fuck It (I Don’t Want You Back)” by Eamon

Eamon is pissed. He dated a ho who gave some other guy head, and he got hurt real bad. While 2003’s “Fuck It” may walk a pretty thin line on the edge of misogyny, replace ho with dick and you’ve got an aggro R&B ballad that doesn’t discriminate. (Alternatively, check out Frankee’s “Fuck You Right Back,” featuring the velour-clad comeback “Your sex was wack.”) Hey, we never said all these songs were classy.—Kate Wertheimer

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“Wrecking Ball” by Miley Cyrus (2013)

“Wrecking Ball” by Miley Cyrus

When the edgy Terry Richardson–directed video for Miley Cyrus’s power ballad was released last year, 400 million YouTubers dropped their jaws at the sight of a naked Cyrus straddling a massive steel ball. All snickers and parody videos aside, the track stands on its own as essential listening for dumpers and dumpees who have gone full-tilt into relationships and wound up emotionally demolished. And the racy video antics? Well, as BFF Lesley told us long ago, she’s just being Miley.—Michael Chen

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“We Are Never Ever Getting Back Together” by Taylor Swift (2012)

“We Are Never Ever Getting Back Together” by Taylor Swift

Taylor Swift’s penchant for mining her own relationship drama to find songwriting gold is well documented; when the results are as catchy and downright fun as this kiss-off gem, we have no complaints. “We Are Never Ever Getting Back Together” finds the country-pop starlet and her ex (reportedly actor Jake Gyllenhaal) traipsing about in that awkward on-again, off-again state of limbo. The back and forth goes on, the ex’s transgressions pile up, but ultimately, “swift justice” wins out and we’re treated to one of the best breakup songs, like, ever.—Michael Chen

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“Since U Been Gone” by Kelly Clarkson (2004)

“Since U Been Gone” by Kelly Clarkson

You may hate American Idol. You may hate power pop. You may hate it when people use u instead of you. But here’s the deal: You may also really hate your ex. And this song (off of Clarkson’s 2004 album, Breakaway) is so goddamned catchy, you can’t not belt out the chorus every time—with feeling.—Kate Wertheimer

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“Torn” by Natalie Imbruglia (1997)

“Torn” by Natalie Imbruglia

Lurking behind the glossy sheen and shimmering guitars of this 1997 global pop hit is the age-old story of a relationship gone sour. “Torn” was originally recorded by American alt rockers Ednaswap, but saucy Aussie Natalie Imbruglia’s rendition perfectly encapsulates the unhappy transition from honeymoon optimism to the realization that “Illusion never changed / Into something real.” Seriously, we totally hate it when that happens.—Michael Chen

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“Un-Break My Heart” by Toni Braxton (1996)

“Un-Break My Heart” by Toni Braxton

Queen of ’90s R&B heartache Toni Braxton delivered more than just another sad love song when “Un-Break My Heart” hit the airwaves in 1996. A mélange of Spanish guitars and Braxton’s sultry contralto vocals, the Grammy-winning single builds a quiet storm with a dramatic crescendo as Braxton pleads with her ex to rewind their doomed relationship back to happier times. If the song’s video is any indication, those happier times included playing Twister and sharing a shower with hunky Polo Ralph Lauren model Tyson Beckford. So, yeah, we feel ya, Toni.—Michael Chen

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“Always on My Mind” by Willie Nelson (1982)

“Always on My Mind” by Willie Nelson

It’s been a hit for other artists—notably Elvis Presley and the Pet Shop Boys—but “Always on My Mind” has never packed more wallop than in Willie Nelson’s recording, the title track of his eponymous 1982 album. Humble and sincere, Nelson’s plea for forgiveness exudes the quiet wisdom of genuine contrition: Having finally opened his eyes, he allows himself to hope that they can still make contact.—Adam Feldman

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“Cry Me a River” by Julie London (1955)

“Cry Me a River” by Julie London

This devastating torch song was written for Ella Fitzgerald in 1953, but Julie London managed to release it before the Queen of Jazz was able to get a version out. It became London’s signature song: Backed by a late-night thrum of guitar and bass that teeters ambiguously between the minor and major keys, her hushed vocals waver between tender, haughty and devastated. And then there’s that classy “too plebeian”/“through with me and” rhyme. They don’t write ’em like this any more.—James Manning

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“Walk On By” by Dionne Warwick (1964)

“Walk On By” by Dionne Warwick

The 1960s songwriting team of Burt Bacharach and Hal David found their perfect interpreter in Dionne Warwick, whose breezy style made the duo’s character-driven, rhythmically challenging tunes sound deceptively simple. In 1964’s “Walk on By,” one of her first Bacharach-David hits, Warwick teases out the smooth dignity in a song about the pain of rejection.—Adam Feldman

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Users say

Rufus B
Rufus B

Bruce Springsteen's "Stolen Car" - devastating. It's over right after it starts... "We got married and promised never to part, then little by little we broke each other's heart..."

I Would add the following...Poke-Frightened Rabbit   Amsterdam-Guster  Burning Photographs-Ryan Adams and How You Like Me Now?-The Haavy