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Best songs about heartbreak
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The 20 greatest songs about heartbreak

Going through a break-up? Soothe your soul with our list of the 20 best heartbreak songs of all time

Written by
Time Out editors
Kate Solomon

Heartbreak is hell, but it's inspired a helluva lot of great pop music – just ask Fleetwood Mac. Our list of the greatest heartbreak songs has been chosen by the DJs from U Suck, an ace Dalston club night devoted to break-up bangers and empowering, screw-you-anyway-mate anthems.  From Robyn to Solange, and Taylor Swift to Gloria Gaynor, these tunes will remind you that however bad you're feeling right now, somebody else has probably had it worse. Oh, and if you still need some feels, check out our list of the 50 best sad songs, too.

The best heartbreak songs of all time

‘Somebody Else’ – The 1975

20. ‘Somebody Else’ – The 1975

For shouty, over-it, see ya anthems (hiya Little Mix), 2016 is hard to beat. But The 1975’s occasionally pretentious ode to post-break-up jealousy took a different tack. Over glistening synths (so synthy it’s like the ’80s sneezed on them), Matt Healy’s breathy delivery drives the feeling home; the green-eyed monster can rear its ugly head even when you’re the one who’s been doing the heartbreaking.

‘The Winner Takes It All’ – Abba

19. ‘The Winner Takes It All’ – Abba

Abba were the absolute grand masters of quietly devastating bubblegum pop. They’ll tell you ‘The Winner Takes It All’ is not about Bjorn and Agnetha’s divorce actually, but the story of having to meet and talk (and work and sing) with the person who recently smashed your heart into a thousand pieces. The festive arpeggios underpinning the whole thing are like a reminder of your wedding day – that happy memory tarnished now by your painful divorce. Love is dead. RIP.

‘We Are Never Ever Getting Back Together’ – Taylor Swift

18. ‘We Are Never Ever Getting Back Together’ – Taylor Swift

One of the first songs Taylor wrote with international hit maestro Max Martin, Swifto’s unabashedly teenage insistence that we are never ever ever getting back together doesn’t feel quite believable – they probably are getting back together, aren’t they? But with its diary-like delivery and massive rant of a chorus it doesn’t really matter if you believe it or not – belting it out while thinking of your own personal flip-flopping, commitment-phobic ratbag feels, like, really good.

‘Lover You Should’ve Come Over’ – Jeff Buckley

17. ‘Lover You Should’ve Come Over’ – Jeff Buckley

A mournful church organ plays as Buckley contemplates the end of a relationship, the end of youth, the end of love... okay, maybe not the end of love. But it’s hard not to fall into a pit of despair as he realises every little mistake he made that led to him losing the love of his life. Writhing at its climax like a heart-sick insomniac, he insists it’s not too late. But it is.

‘Rolling in the Deep’ – Adele

16. ‘Rolling in the Deep’ – Adele

Break-ups are Adele’s bread and butter and while some favour the mournful ‘Someone Like You’, the righteous anger of ‘Rolling in the Deep’ is hard to top. Would that we all had Adele’s voice to roar out that bluesy disdain for the moron who left us. The vengeful choir snapping ‘You’re gonna wish you never had met me’ childishly as she spells out exactly what could have been and what has been lost is almost as satisfying as the vocal fireworks Adele busts out in the chorus.
‘Losing You’ – Solange

15. ‘Losing You’ – Solange

If Solange and Dev Hynes outfit Blood Orange are a match made in louche pop’n’B heaven – and they are – ‘Losing You’ is the track that would be playing as you roll up to the pearly gates. The retro vibe of the irresistibly swaggering beat is tempered by the gentle, almost girlish vocals woven through it. The dying embers of a relationship never made us want to dance more.

‘You Oughta Know’ – Alanis Morissette

14. ‘You Oughta Know’ – Alanis Morissette

With ‘I want you to know that I’m happy for you’ sung with such bile, you’re quite sure that no one has ever been less happy for anyone in the history of the world – and that’s before the song has even kicked off. The jangling ’90s guitar swoops in while Alanis whoops, hollers and growls her way through a comprehensive list of the ways she’s been wronged, the quiet bits only adding to the menace. The absolute bottom line in angry break-up music.

‘Always on My Mind’ – Willie Nelson

13. ‘Always on My Mind’ – Willie Nelson

Elvis gave it a good go, the Pet Shop Boys an arguably a better one, but neither top Willie Nelson for pure regret as he insists that although he was an atrocious boyfriend, you were always his number one thought. Too little too late, as another bastion of break-up pop hits might say.

‘Against All Odds (Take a Look at Me Now)’ – Phil Collins

12. ‘Against All Odds (Take a Look at Me Now)’ – Phil Collins

The song that could soundtrack ‘Yer Da’s Taking The Divorce Well: The Movie’, we defy any of you to get through Phil Collins’s punt on getting his first wife back without punching the air once or twice. So perfectly over the top, so completely ridiculous you can’t help but love it. Try it at karaoke: you might not get your ex back, but by god you’ll have a nice time trying.

‘When Doves Cry’ – Prince

11. ‘When Doves Cry’ – Prince

There aren’t many songs that manage to express pain while simultaneously placing all the blame for a failed relationship on the parents, but such is the beauty of Prince. One of the songs he wrote for ‘Purple Rain’, it opens with an audacious guitar solo that doesn’t exactly sound like it’s coming from a man taking responsibility for his own actions. It paints the scene over a spiky industrial beat, climaxing with Prince screeching his tiny heart out like a petulant teenager.
‘Since U Been Gone’ – Kelly Clarkson

10. ‘Since U Been Gone’ – Kelly Clarkson

Catharsis doesn’t come much more satisfying than an ‘American Idol’ winner’s Yeah Yeah Yeahs-inspired indie-pop-crossover. Building from a lone riff into a wailing power chorus that perfectly skewers her ex by informing him that things are much better now that he’s done one, actually, cheers, it comes with all the perfectly timed pauses and redemptive key changes you’d expect from a Max-Martin-helmed hit.
‘The Tracks of My Tears’ – Smokey Robinson and The Miracles

9. ‘The Tracks of My Tears’ – Smokey Robinson and The Miracles

The Motown crew certainly knew their way around heartbreak and this is the pinnacle of the crying on the inside oeuvre. An economical hit laden with The Miracles’ dreamy harmonies, it’s said that there wasn’t a dry eye in the house any time Smokey and the Miracles performed it.

‘Hey, That’s No Way to Say Goodbye’ – Leonard Cohen

8. ‘Hey, That’s No Way to Say Goodbye’ – Leonard Cohen

The wrong hotel room with the wrong woman. Cohen paints the goodbye scene as poetically as was his way, and it’s not so much sad as resigned, rolling gently through the lovers’ final morning together. With just a handful of consecutive notes making up the melody, it’s a soothingly monotonous affair – no fireworks, no explosive fuck-yous, just the natural end of something that probably wasn’t really right to begin with.

‘Sorry’ – Beyoncé

7. ‘Sorry’ – Beyoncé

The Beyoncé of yore might have put all your shit in a box to the left to the left but nowadays you’ll be lucky if she doesn’t set fire to the lot of it. The infidelity story of 2016’s ‘Lemonade’ is neatly summed up by the closing line, ‘You better call Becky with the good hair’ – and hearing a pissed-off Beyoncé sing ‘Suck on my balls’ is something we’ll treasure forever.
‘I Will Survive’ – Gloria Gaynor

6. ‘I Will Survive’ – Gloria Gaynor

One of the most empowering songs ever written, there’ll come a point during every break-up when you’ll finally feel ready to put it on and let Gloria tell you you’re going to be absolutely fine through the medium of disco so glitzy you can’t close your eyes without seeing glitter balls. It’s the only song ever to have won a Grammy for Best Disco Recording. Possibly because it’s the only disco song worthy of it (and certainly not just because they discontinued the award after only one year).

‘Back to Black’ – Amy Winehouse

5. ‘Back to Black’ – Amy Winehouse

This throwback ballad represents the late, great Amy Winehouse at the peak of her powers. Flanked by Mark Ronson's sumptuous Motown-influenced production, her vocals are loaded with heartbroken emotion as she mourns the end of a messy relationship. 'Life is like a pipe, and I'm a tiny penny rollin' up the walls inside,' she sings despondently, offering one of many stunning couplets. What a singer – but also, what a songwriter.

‘Dancing on My Own’ – Robyn

4. ‘Dancing on My Own’ – Robyn

Since it peaked at a respectable number eight in 2010, this superb electro-disco banger has acquired near-mythical status. It's the tears-on-the-dancefloor anthem of our generation because Robyn totally captures the stinging agony of unrequited love, but makes it kinda defiant at the same time. She may not be the guy he's taking home, but hey, she's still dancing on her own.

‘Love Will Tear Us Apart’ – Joy Division

3. ‘Love Will Tear Us Apart’ – Joy Division

The very concept of love tearing us apart is enough to set the heart aching, let alone putting Ian Curtis’s haunting vocals to a jaunty melody that makes us want to dance and hug people knowing the pain that underpins the whole thing. That the song was released after Curtis’s suicide adds yet another layer of despair, leaving us questioning of the very nature of love.
‘Yes’ – McAlmont & Butler

2. ‘Yes’ – McAlmont & Butler

It’s impossible to listen to this song without feeling better about everything. With strings so ’90s it’s almost painful, the song was originally written to tell the bands they’d been kicked out of where to stick it (Suede for Butler, Thieves for McAlmont) but it works just as well as a screw-you to the ex that comes creeping with that 3am ‘wuu2’ text.

‘You Can Go Your Own Way’ – Fleetwood Mac

1. ‘You Can Go Your Own Way’ – Fleetwood Mac

It takes a certain kind of guts to write a song about a fellow band member – so clearly placing all the blame for the breakdown of the relationship on her – and then expect her to perform it on stage with you, but that’s what Lindsey Buckingham did. Stevie Nicks wasn’t super into it, but it remains one of the Mac’s best songs. Sometimes the only way to deal with a broken heart is to become small-minded and pettily disdainful of everything your ex has ever done. And this is the song to do it to.

Go on, let it all out...


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