The 50 best break-up songs

Heaven knows you’re miserable now – so you may as well enjoy it with the best break-up songs ever made



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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 expletive king Cee Lo Green attest. So we invite you to celebrate the heartbreak – whether angry, suicidal or just a bit sad – with our collection of the best break-up songs ever recorded.

Did we miss out your favourite favourite sountrack to sadness? Let us know in the comments box below or tweet us at @TimeOutMusic.

Count down our 50 best break-up songs: 50–41


'Fuck You' – Cee-Lo Green

An old-school Motown-style soul number with a gleefully foul mouth, ‘Fuck You’ was Cee Lo Green’s first solo single after he’d spent years crooning for Goodie Mob and Gnarls Barkley. It’s a shout-along, four-minute middle finger to a gold-digging ex (despite Green unconvincingly recasting it as a dig at the music industry), packing in punning verses, a wailing bridge and that glorious quadruple-fuck chorus. Even though the version everyone heard on the radio was heavily censored and retitled ‘Forget You’, it was one of the biggest songs of 2010. Needless to say, no one was singing the bowdlerised version. Forget that. James Manning

Watch 'Fuck You' video  |  Buy this song on iTunes

“Wrecking Ball” by Miley Cyrus (2013)

'Wrecking Ball' – 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 and swinging on 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. Yes, folks, the wrecking ball is a metaphor. And the racy video antics? Well, as BFF Lesley told us long ago, she’s just being Miley. Michael Chen

Watch 'Wrecking Ball' video  |  Buy this song on iTunes

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

'Somebody That I Used to Know' – Gotye feat Kimbra

Wouter De Backer, AKA 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

Watch 'Somebody That I Used To Know' videoBuy this song on iTunes

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

'We Are Never Ever Getting Back Together' – 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 break-up songs, like, ever. Michael Chen

Watch 'We Are Never Ever Getting Back Together' video  |  Buy this song on iTunes


'Cry Me a River' – Julie London

When it comes to the music of heartbreak, it takes a lot to beat Ella Fitzgerald. But Julie London managed it, releasing this devastating torch song (written for Fitzgerald in 1953) 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

Listen to 'Cry Me a River' on YouTube  |  Buy this song on iTunes

“Torn” by Natalie Imbruglia (1997)

'Torn' – 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 realisation that ‘illusion never changed / into something real’. Seriously, we totally hate it when that happens. Michael Chen

Watch 'Torn' video  |  Buy this song on iTunes

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

‘Un-Break My Heart' – 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

Watch 'Un-Break My Heart' video  |  Buy this song on iTunes

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

'Always on My Mind' – 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

Listen to 'Always On My Mind' on YouTube  |  Buy this song on iTunes

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

'Since U Been Gone' – 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

Watch 'Since U Been Gone' video  |  Buy this song on iTunes

“Walk On By” by Dionne Warwick (1964)

'Walk on 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

Listen to 'Walk On By' on YouTube  |  Buy this song on iTunes

  1. 50–41
  2. 40–31
  3. 30–21
  4. 20–11
  5. 10–1

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