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The 50 best break-up songs

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

Written by
Time Out editors

Breaking up is hard to do – so hard, in fact, that most of the best pop music ever produced (as well as a raft of tearjerking break-up films) has sprung from its well of agony. 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. So, after picking the best love songs, we decided to celebrate heartbreak too with our collection of the best break-up songs ever recorded.

RECOMMENDED: The best songs ever

'Fuck You' – Cee-Lo Green

50. '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

'Train in Vain' – The Clash

49. 'Train in Vain' – The Clash

This song, tacked on to the end of 1979’s ‘London Calling’, is not for wallowing. It’s the song you play when you’re emerging from that post-break-up anger and are ready to rock (and maybe even dance) again. It’s for the moments when you feel simultaneously like the bigger person and also self-satisfied in your accusations against your former lover. It’s absolutely necessary during break-ups, and a pretty great tune the rest of the time as well. Kate Wertheimer

Listen to 'Train in Vain' on YouTube  |  Buy this song on iTunes

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

48. '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' – Taylor Swift

47. '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

'River' – Joni Mitchell

46. 'River' – Joni Mitchell

A broken heart isn’t just for those who’ve been broken up with – as ‘River’ attests, a break-up anthem that sounds as crisp and sad-in-the-bones today as it did when it was released as part of Joni Mitchell’s perfectly titled ‘Blue’ album in 1971. ‘I’m so hard to handle, I’m selfish and I’m sad, now I’ve gone and lost the best baby that I ever had,’ sings Mitchell, then later, ‘I made my baby say goodbye.’ The song is thought to have been written about Mitchell’s decision to end her relationship with Graham Nash – who in turn released his astonishingly tender ‘Songs for Beginners’ album. Both records are generous gifts for anyone nursing a wounded heart. Sophie Harris

Listen to 'River' on YouTube  |  Buy this song on iTunes

'Torn' – Natalie Imbruglia

45. 'Torn' – Natalie Imbruglia

Let's be real: 'Torn' by Natalie Imbruglia is one of the best songs of the '90s. It still sounds great whether you catch it on daytime radio while waiting for a haircut or on the dance floor at a mate's wedding. "There's nothing where he used to lie, my inspiration has run dry," Imbruglia croons on the bridge, perfectly encapsulating the stale fug of a broken relationship. Somewhat shockingly, her version (which became a huge global hit in 1997) is actually a cover of the original by little known Aussie band Ednaswap. Who knew, right? Nick Levine

Watch 'Torn' video  |  Buy this song on iTunes

'When You Were Mine' – Prince

44. 'When You Were Mine' – Prince


Fact: this (relatively) underrated Prince gem is one of Frank Ocean's favourite songs. It's easy to see why the elusive one would fall for 'When You Were Mine': it's a devastatingly direct and desperate ode to the one who's slowly slipping away from you. "I know that you're going with another guy," Prince sings on the chorus. "I don't care - because I love you baby, that's no lie." Gulp.

Prince's funky original is matched by Cyndi Lauper's new wave cover version, in which she preserves the song's male pronouns ("Now I spend my time following him whenever he's with you"), giving the song an intriguing queer edge. Nick Levine

Listen to 'When You Were Mine' on YouTube  |  Buy this song on iTunes

'Always on My Mind' – Willie Nelson
Image: Columbia

43. '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' – Kelly Clarkson
Image: RCA

42. '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' – Dionne Warwick
Image: Scepter

41. '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

'There's a Ghost in My House' – R Dean Taylor

40. 'There's a Ghost in My House' – R Dean Taylor

Think you’ve been through some messy break-ups? RDT has a spooky story that’ll beat them all. His baby’s gone, but he can’t get over her – and then weird stuff starts happening… to an infectious Motown beat! Hear those thumping footsteps on the stairs, shiver in fright at the weird apparition in R’s coffee cup, and remember: no matter how much you may want to, you can’t exorcise your ex. James Manning

Listen to 'There's a Ghost In My House' on YouTube  |  Buy this song on iTunes

'It’s Too Late' by Carole King

39. 'It’s Too Late' by Carole King

Carole King’s era-shaping 1971 album, ‘Tapestry’, was in some sense a declaration of independence from Gerry Goffin, her former husband and songwriting collaborator. The album’s first single, ‘It’s Too Late’, treats the end of a once-cherished relationship with bittersweet maturity, strength and striking lack of recrimination: ‘Still I’m glad for what we had / And how I once loved you.’ It’s a song about being realistic about the end – a sentiment made all the more moving by its initial pairing, as a single, with the tremblingly erotic ‘I Feel the Earth Move’. Adam Feldman

Listen to 'It's Too Late' on YouTube  |  Buy this song on iTunes

'I Want You Back' – The Jackson 5

38. 'I Want You Back' – The Jackson 5

What the hell does an 11-year-old know about loss? With a tip of his giant purple pimp hat, Michael sang this Motown peak with a mile-wide smile on ‘The Ed Sullivan Show’ in ’69. Still, the kid sold it like nobody else, over chords that rise and fall like a roller coaster. And nothing hurts like first love. Brent DiCrescenzo

Listen to 'I Want You Back' on YouTube  |  Buy this song on iTunes

'Don’t Speak' – No Doubt

37. 'Don’t Speak' – No Doubt

‘Don’t Speak’ was released in 1996 as the third single from No Doubt’s third album, ‘Tragic Kingdom’. The song, which Gwen Stefani penned in response to her break-up with bandmate Tony Kanal, became the band’s most successful international single – and a rallying cry for lovelorn souls the world over to go right ahead and bury their heads in the sand. Kristen Zwicker

Watch 'Don't Speak' video  |  Buy this song on iTunes

'Crying' – Roy Orbison
Image: Monument

36. 'Crying' – Roy Orbison

Roy Orbison’s 1961 ballad is sensitive almost to a fault: the confession of a total bawler, reduced to tears even by touching the hand of the woman who broke his heart. But the emotion soaked into Orbison’s rich, quavering voice is offset by the singer’s disciplined, deadpan cool. Even when baring his sobbing soul, he somehow seems unflappable. Adam Feldman

Listen to 'Crying' on YouTube  |  Buy this song on iTunes

'Skinny Love' – Bon Iver

35. 'Skinny Love' – Bon Iver

You don’t even need to be able to understand the words in this 2007 hipster break-up anthem to recognise that this is the sound of a man in pain. Justin Vernon’s post-break-up isolation in a rural Wisconsin cabin for one lonely winter is now the stuff of indie-folk legend. But for a singer-songwriter who became known for his ethereal falsetto, it’s surprising how truly angry he sounds here. The lyrics are obtuse, but the clearer ones (‘I tell my love to wreck it all, / Cut out all the ropes and let me fall’) paint a vivid emotional picture. Jenna Scherer

Listen to 'Skinny Love' on YouTube  |  Buy this song on iTunes

'I Just Don’t Think I’ll Ever Get Over You' – Colin Hay

34. 'I Just Don’t Think I’ll Ever Get Over You' – Colin Hay

Although Scottish-born Australian Hay might be best known for his work with Men At Work and their monster good-time hit ‘Down Under’, his later work has revealed a sensitivity and melancholy that is at times both beautiful and heart-wrenching. It’s nigh on impossible to listen to ‘I Just Don't Think I'll Ever Get Over You’, with its exquisitely haunting story of love and loss, without welling up and shedding a few tears. This song should only be listened to late at night in a dimly lit room, on your own, with the rain obscuring the view of the city lights outside your window – allow yourself to let go, boo your eyes out, think of every unrequited love that’s ever stayed with you and twisted you inside out, and then let Hay’s smooth voice and resigned agonised lyrics articulate every ounce of pain inside. After that, make yourself a cup of tea, pull yourself together and get yourself back on to find yourself someone else who’ll inevitably break your heart as well. Tim Arthur

Listen to 'I Just Don’t Think I’ll Ever Get Over You' on YouTube  |  Buy this song on iTunes

'Teardrops' – Womack & Womack
Image: Island Records

33. 'Teardrops' – Womack & Womack

A classic in the genre of Songs to Cry to in Clubs (see also ‘Dancing On My Own’ by Robyn), this 1988 electrodisco anthem tells the tale of a cheating heart haunted by its infidelity. ‘Footsteps on the dance floor / Remind me, baby, of you / Teardrops in my eyes / Next time I’ll be true.’ The song comes from Cecil (brother of Bobby) Womack and his wife, Linda – a formidable musical partnership throughout the ’80s and ’90s. This is their biggest and best hit, however, and responsible for plenty of tear-stained dancing shoes over the years. Jonny Ensall

Watch 'Teardrops' video  |  Buy this song on iTunes

'Believe' – Cher

32. 'Believe' – Cher

If you don’t think this is a brilliant song, then it’s probably only because you’ve heard it way too many times. Cher’s (temporary) resurrection as a dance-pop diva in 1998 has raised plenty of hackles over the years – not least for its then-unprecedented use of Auto-Tune – but at its heart it’s simply a great break-up song in the air-punchingly empowered tradition of ‘I Will Survive’: ‘I’ve had time to think it through / And maybe I’m too good for you.’ When we’re going through a rough time, we could all use a bit of that attitude. James Manning

Watch 'Believe' video  |  Buy this song on iTunes

'Say Hello, Wave Goodbye' – Soft Cell

31. 'Say Hello, Wave Goodbye' – Soft Cell

‘Take your hands off me!’ cries Marc Almond on this 1982 synth-pop tearjerker. ‘I don’t belong to you, you see.’ The follow-up to Soft Cell’s hit single ‘Tainted Love’, ‘Say Hello’ perfectly encapsulates the ambivalence and denial at love’s end. Almond reflects that the pair must’ve been ‘the standing joke of the year’, adding later, ‘I never knew you / You never knew me.’ And of course, were any of this true, you wouldn’t be crying now, would you? Sophie Harris

Listen to 'Say Hello, Wave Goodbye' on YouTube  |  Buy this song on iTunes

'I Keep Forgettin’' – Michael McDonald

30. 'I Keep Forgettin’' – Michael McDonald

We don’t typically think of the break-up song as a climate hospitable to sultry funk, but somebody forgot to notify Michael McDonald. On this 1982 lite-rock staple, the former Doobie Bro laments being hung up on an ex, as a rhythm section stocked with session aces glides through a monster groove – famously sampled by Warren G on 1994’s ‘Regulate’. Whoever the subject of the tune was, it’s hard to imagine her not shimmying back into the husky crooner’s arms when she heard this immortal jam. Hank Shteamer

Listen to 'I Keep Forgettin’' on YouTube  |  Buy this song on iTunes

'I'm Aquarius' – Metronomy

29. 'I'm Aquarius' – Metronomy

We may have iPhones and pulled pork sliders to comfort and distract us nowadays, but break-ups are still as hard as they’ve ever been. Just ask electro-pop act Metronomy, who released this lo-fi melancholy meander at the tail-end of last year. It’s a sad and bitter modern story that finds singer Joe Mount musing on an ex that upped and left, blaming their incompatibility on clashing horoscopes. That old chestnut, eh? Okay, so you’re clearly better off without anyone who uses that as a reason to break up – but it still hurts. Tristan Parker

Watch 'I'm Aquarius' video  |  Buy this song on iTunes

'Irreplaceable' – Beyoncé
Image: Columbia

28. 'Irreplaceable' – Beyoncé

The Destiny’s Child songbook is a bible for the woman looking to keep her man on his toes. Just in case ‘Bills, Bills, Bills’, ‘Say My Name’ and ‘Survivor’ didn’t send a clear enough message, Beyoncé reiterated her ‘Don’t get too comfortable’ party line on this, the ultimate kick-you-to-the-curb anthem. The singer doesn’t sound the slightest bit perturbed as she shoos a disappointing lover out of her crib, advising him that he’ll find his worldly possessions ‘in a box to the left’. You’re tempted to shout out an ‘Amen’. Hank Shteamer

Watch 'Irreplaceable' video  |  Buy this song on iTunes

'Ex-Factor' – Lauryn Hill
Image: Columbia

27. 'Ex-Factor' – Lauryn Hill

‘Doo Wop (That Thing)’ may have been the flagship single from Lauryn Hill’s post-Fugees solo debut – 1998’s multi-Grammy-winning ‘The Miseducation of Lauryn Hill’ – but it was the languid, lovely ‘Ex-Factor’ that rocketed the disc into the realms of extraordinary. Perfectly piquant down to the name of the song, ‘Ex-Factor’ longs for things to be different while knowing they can’t be, ringing with frustration (‘I keep letting you back in’) but humming with a love that refuses to fade. Sophie Harris

Watch 'Ex-Factor' video  |  Buy this song on iTunes

'I Just Don’t Know What to Do With Myself' – White Stripes
Image: XL

26. 'I Just Don’t Know What to Do With Myself' – White Stripes

Though this Bacharach-David song was originally sung by Tommy Hunt in 1962 (and has since been covered by myriad musicians, including Dusty Springfield, Dionne Warwick, Isaac Hayes and Elvis Costello), no-one has been able to capture the desperation – and frustration – behind the lyrics quite like Jack White III. Recorded for the 2003 White Stripes album, ‘Elephant’, this rock ’n’ roll version is perfect for the transition from heartbroken to pissed off. Bonus: Sofia Coppola directed a lingerie-clad, pole dancing Kate Moss in the music video, which should at least help get your blood pumping again. Kate Wertheimer

Watch 'I Just Don’t Know What to Do With Myself' video  |  Buy this song on iTunes

'Pain in My Heart' – Otis Redding

25. 'Pain in My Heart' – Otis Redding

Over and again, whether hopeful or heartbreaking, Otis Redding’s exquisite love songs bring us to our knees, like this title track off the soul icon’s 1964 debut album for Stax Records subdivision Volt (which also includes the imploring ‘These Arms of Mine’). If you’re really in the mood to wallow, mourn the fact that Redding perished in a plane crash at age 26, just three days after recording ‘Dock of the Bay’. Kate Wertheimer

Listen to 'Pain In My Heart' on YouTube  |  Buy this song on iTunes

'Dry Your Eyes' – The Streets

24. 'Dry Your Eyes' – The Streets

Men’s emotions can sometimes be harder to read than a pureed copy of Proust. In 2004, however, The Streets’ Mike Skinner just laid it right on the line. While Skinner’s verses found him crestfallen at having been chucked, it’s the choruses that made the tune so beloved, delivering man-to-man comfort and kindly reassurances that there are ‘plenty more fish in the sea’. Oliver Keens

Watch 'Dry Your Eyes' video  |  Buy this song on iTunes

'Heartbreak Hotel' – Elvis Presley

23. 'Heartbreak Hotel' – Elvis Presley

Think your break-up is sad? This song’s lyrics were inspired by a 1956 newspaper article about a man who jumped to his death from a hotel window, leaving a note with the single line ‘I walk a lonely street’. But suicides don’t sell records, so Presley crooned instead about a place where the bellhop’s tears flow, the desk clerk dresses in black and broken-hearted lovers can cry away their gloom. (And potentially hook up? Was this place also a brothel? No?) Kate Wertheimer

Listen to 'Heartbreak Hotel' on YouTube  |  Buy this song on iTunes

'Back for Good' – Take That

22. 'Back for Good' – Take That

Regretting something you did that screwed up a relationship is one thing, but gladly offering yourself as a scapegoat for anything in the hope of getting one more shot at that eternally doomed relationship… That’s when you know the hooks are in deep. Gazza Barlow and co nail that desperate, exasperated post-break-up cry-for-help perfectly in ‘Back for Good’ – clearly the best song they (ie Barlow) ever wrote. ‘In the twist of separation, you excelled at being free – can’t you find a little room inside for me?’ begs Gazza. It’s hardly dignified, but we’ve all been there. Tristan Parker

Watch 'Back For Good' video  |  Buy this song on iTunes

'I Know It’s Over' – The Smiths

21. 'I Know It’s Over' – The Smiths

Morrissey, the patron saint of very British heartbreak, outdid himself with this one. ‘I Know It's Over’ is one of his finest lyrics, an introspective portrait of romantic frustration with too many slyly devastating lines to quote – though that won’t stop us. Many a book-filled bedroom has been haunted by the question, ‘If you're so clever / Then why are you on your own tonight?’ Then, slipped into the song’s centre, comes the killer blow: 'I know it's over / And it never really began / But in my heart it was so real.’ And Johnny Marr’s guitar line rises and falls like a lover’s shattered hopes. James Manning

Listen to 'I Know It's Over' on YouTubeBuy this song on iTunes

'Against All Odds (Take a Look At Me Now)' – Phil Collins

20. 'Against All Odds (Take a Look At Me Now)' – Phil Collins

When you’re dumped, you’re allowed to indulge in melodrama. It is acceptable to sit around in a robe for days and take big bites of the pillow synthesisers, ice-cream crooning and cookie-dough drums comprising this most powerful and ballad-y of power ballads. A leftover from his solo debut that was recorded years later, in 1984, for a Jeff Bridges cheese-noir flick, ‘Against All Odds’ gave the former Genesis man his first Number One hit in America. Brent DiCrescenzo

Watch 'Against All Odds (Take A Look At Me Now)' video  |  Buy this song on iTunes

'Without You' – Harry Nilsson

19. 'Without You' – Harry Nilsson

Always pushing his liver and vocal cords to the limit, Nilsson injected histrionics and heart into the songs he covered like HGH. His take on Randy Newman’s ‘Living Without You’ is downbeat perfect. A year later, this Badfinger tune amped up the woe-is-me. Fact: it is impossible to listen to this Kleenex-consuming epic without balling your hands into fists and mock-karaokeing along. Next song on the album? ‘Coconut’. Drink the pain away. Brent DiCrescenzo

Listen to 'Without You' on YouTube  |  Buy this song on iTunes

'Survivor' – Destiny's Child

18. 'Survivor' – Destiny's Child

‘Survivor’ might well be the noughties conclusion of Gloria Gaynor’s 1978 disco hit, ‘I Will Survive’, but Destiny’s Child don’t just re-tell Gaynor’s story of triumph after relationship tragedy – they show the listener how to kick heartbreak squarely in the balls and stamp on its throat with a stiletto the size of a stepladder. Whereas Gaynor gradually grew strong and ‘learned how to get along’, Beyoncé and crew don’t waste any time lamenting, opening the song with ‘Now that you’re out of my life / I’m so much better’ before finishing the first verse with a matter-of-fact reminder: ‘You thought I wouldn’t sell without you / Sold nine million.’ Break-up? What break-up? Or even just: ‘What?’ Tristan Parker

Watch 'Survivor' video  |  Buy this song on iTunes

'How Can You Mend a Broken Heart' – Al Green
Image: Hi

17. 'How Can You Mend a Broken Heart' – Al Green

Look, just because you’ve had your heart broken, it doesn’t mean that your mojo has to wilt away and die too – and the Reverend Al is here to spell that out via his definitive 1972 version of the Bee Gees’ cut. He aches just like you, but his hope hasn’t died (‘Please help me mend my broken heart / And let me live again’) – and Al’s signature slow, sensual soul arrangements prove that it’s not just his heart that’s stirring. Kate Wertheimer

Listen to 'How Can You Mend a Broken Heart' on YouTube  |  Buy this song on iTunes

'Tangled Up in Blue' – Bob Dylan

16. 'Tangled Up in Blue' – Bob Dylan

Jakob Dylan once said that listening to his father’s 1975 album, ‘Blood On The Tracks’, was like listening to his parents fighting. You can hear why on its opening track, ‘Tangled Up in Blue’ – a song that feels lived-in, true and intimate, and at the same time assumes an Odyssean quality. Inspired by Dylan’s split from his wife Sara, the song finds our narrator caught between throw-in-the-towel resignation and deep, soul-shuddering longing: tangled up in blue. Sophie Harris

Watch 'Tangled Up In Blue' video  |  Buy this song on iTunes

'Tracks of My Tears' – Smokey Robinson And The Miracles

15. 'Tracks of My Tears' – Smokey Robinson And The Miracles

Ah, the tears of a clown. Smokey might, indeed, ‘be the life of the party’, but ‘deep inside [he’s] blue’, people. As with the best soulful weepers, ‘Tracks’ beautifully and economically articulates the pain of missing the one that got away. This summer-of-’65 staple – a cocktail of Smokey’s golden voice, swirling strings and horns, and a sing-along-worthy chorus – rings just as true today. Tim Lowery

Listen to 'Tracks of My Tears' on YouTube  |  Buy this song on iTunes

'Hey, That's No Way to Say Goodbye' – Leonard Cohen
Image: Columbia

14. 'Hey, That's No Way to Say Goodbye' – Leonard Cohen

Tear-jerking Canadian troubadour Cohen has many a song in his arsenal to reduce grown men and women to pathetic wistfulness, but this 1967 beauty is the most effective of them all. Its set-up is simple – two lovers remember the happy times even as they part, via Cohen’s sweet, sad lyrics: ‘You know my love goes with you as your love stays with me / It’s just the way it changes, like the shoreline and the sea.’ What makes it a classic, however, is how upbeat Cohen’s picked guitar, boingy mouth harp and evocative similes feel against the reality of the situation, deftly demonstrating that losing someone can be painful but incredibly cathartic. Jonny Ensall

Listen to 'Hey, That's No Way To Say Goodbye' on YouTube  |  Buy this song on iTunes

'Back to Black' – Amy Winehouse
Image: Island Records

13. 'Back to Black' – Amy Winehouse

The late singer-songwriter crooned plenty about addiction, depression and heartbreak, but nowhere more brutally than in this moody torch song, which gave its title to her 2007 album. Winehouse penned this hit single about her falling back into bad habits after her very public break with husband Blake Fielder-Civil. The gloomy repetition of the word ‘black’ during the bridge is the sound of a spiral into darkness – albeit a funky one. Jenna Scherer

Watch 'Back to Black' video  |  Buy this song on iTunes

'What Becomes of the Brokenhearted' – Jimmy Ruffin

12. 'What Becomes of the Brokenhearted' – Jimmy Ruffin

What becomes of the brokenhearted? They end up listening to this solid-gold soul classic over and over again, is what. The sad and newly single can find solace in its driving, determined verses, tantalising string refrain, major-to-minor key changes, and knowledge that yes, we’ve all been through it, and survived. Recorded in 1966 for Motown, the song is among the label’s most covered hits. Anyone who’s turned to music for comfort (that’ll be all of us, then) will understand why. Sophie Harris

Listen to 'What Becomes of the Brokenhearted' on YouTube  |  Buy this song on iTunes

'Don't Leave Me This Way' – Harold Melvin And The Blue Notes

11. 'Don't Leave Me This Way' – Harold Melvin And The Blue Notes

Yes, there are other versions. Thelma Houston and The Communards both famously took this Gamble & Huff-written Philly disco cavalcade to the top of the charts. But nothing compares to the way Teddy Pendergrass’s rich and thunderous rasp emotes loss and completely connects the brain to the body. Oliver Keens

Listen to 'Don't Leave Me This Way' on YouTube  |  Buy this song on iTunes

'I Will Always Love You' – Whitney Houston

10. 'I Will Always Love You' – Whitney Houston

Dolly Parton wrote and recorded this song in 1973 as a rueful envoi for her mentor and champion, Porter Waggoner, and later reprised it in the 1982 movie musical ‘The Best Little Whorehouse in Texas’. Although both of those versions hit the top of the country charts, the song reached its cultural apotheosis in Whitney Houston’s epic 1991 version from the soundtrack to ‘The Bodyguard’; at the time, it was the best-selling American single in history. In Houston’s soulful account, the song moves from a quiet, a cappella intro to a blast of gospel-inflected nobility and suffering – and then drifts upward into quiet again at the very end, as though ascending to a state of grace. Adam Feldman

Watch 'I Will Always Love You' video  |  Buy this song on iTunes

'No Distance Left to Run' – Blur

9. 'No Distance Left to Run' – Blur

From the bleak opening line – ‘It’s over, you don’t need to tell me’ – to Damon Albarn’s final cries, this song is like a punch to the gut. Written, allegedly, about Albarn’s split with Elastica frontwoman Justine Frischmann, the tune perfectly encapsulates the weariness and resignation all too often experienced during a break-up, in that period between acceptance and finally moving on. Sigh. Amy Plitt

Watch 'No Distance Left to Run' video  |  Buy this song on iTunes

'You Oughta Know' – Alanis Morissette

8. 'You Oughta Know' – Alanis Morissette

Purported subject of this song Dave ‘Uncle Joey’ Coulier insists that his break-up with Alanis was amicable. But there’s nothing well-wishing about this most vengeful of jilted-lover odes, the object of many a cathartic karaoke jam since its release in 1995. Like all great rages, Alanis lets hers build: the tune begins like an unexploded bomb, and you can almost smell the cordite in the air as she murmurs: ‘I want you to know / I’m happy for you…’ And then the guitar kicks in, and the uncomfortable questions begin: ‘Is she perverted like me? / Would she go down on you in a theatre?’ By the time she’s growling about scratching her nails down someone else’s back and hoping you feel it, it’s already too late, Coulier. This one’s for the most demonstrative of your five stages: white-hot anger. Jenna Scherer

Watch 'You Oughta Know' video  |  Buy this song on iTunes

'I Heard It Through the Grapevine' – Marvin Gaye

7. 'I Heard It Through the Grapevine' – Marvin Gaye

You know even before the drumbeat kicks in that something is gonna go down in this song. And for anyone who’s had to hear the cheatin’, lyin’ news from someone else, this 1968 Motown single hits home. It’s become an acclaimed, Grammy Hall of Fame soul classic, covered by a range of musicians including Creedence Clearwater Revival (who made an 11-minute version for their 1970 album ‘Cosmo’s Factory’) and claymation group the California Raisins (grapevine, raisins, see what they did there?). Kate Wertheimer

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'You’ve Lost That Lovin’ Feelin’' – The Righteous Brothers

6. 'You’ve Lost That Lovin’ Feelin’' – The Righteous Brothers

Love crashes into a wall – specifically, producer Phil Spector’s trademark ‘Wall of Sound’ – in this landmark blue-eyed-soul lament, the twentieth century’s most-played song on radio and TV. Co-written by Spector, Barry Mann and Cynthia Weil, the song begins with a sharply specific observation (‘You never close your eyes any more when I kiss your lips’) that leads inevitably to the chorus’s pained conclusion. But the song’s slowness and length – in 1964, 3:45 was an eternity for radio pop – give it an aching tenderness that makes its final exhortation to ‘bring back that lovin’ feelin’’ sound like it has some hope of success. Adam Feldman

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'I Will Survive' – Gloria Gaynor

5. 'I Will Survive' – Gloria Gaynor

Is there any song that combines female empowerment and discofied schmaltz with the same efficacy as Gloria Gaynor’s ‘I Will Survive’? With lyrics like ‘I’ve got all my life to live / I’ve got all my love to give / And I’ll survive, I will survive’ – not to mention a soaring melody accented by horns and strings galore – probably not. In fact, we think the Grammy-winning hit, released in late 1978, is one of the best ‘screw you, loser – I’m over you’ tunes of all time. Bruce Tantum

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'Nothing Compares 2 U' – Sinead O’Connor

4. 'Nothing Compares 2 U' – Sinead O’Connor

Originally written and composed by Prince, ‘Nothing Compares 2 U’ didn’t reach iconic, heart-decimating status until a certain headstrong Irish singer-songwriter tried her hand – and those sad, sad eyes – at covering it in 1990. The video, which alternates between a stark close-up of O’Connor’s despair-wrought face and shots of the dark-cloaked songstress roaming through the Parc de Saint-Cloud (a historic park just outside of Paris), was cited by Miley Cyrus as the inspiration for her 2013 ‘Wrecking Ball’ video. Whatever your opinion of that spectacle, it can’t be denied that more than two decades later, O’Connor’s wrenching rendition still packs a punch. Kristen Zwicker

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'Someone Like You' – Adele

2. 'Someone Like You' – Adele

You’d have to be some kind of monster not to mist up a bit at Adele’s 2011 tear-tugger. A ‘Saturday Night Live’ sketch has been written about its irresistible emotional pull; even dogs, it seems, are not immune. Part of what gives the song this power, paradoxically, is its rejection of sadness. The heartbroken singer enacts a performance of brave stoicism (she’s fine, she’ll move on, she’ll find someone else), but we know that she is fooling herself (she’s a mess, she’s still stuck, the best someone else is still the guy she has lost). But her wilful refusal to cry about it lets us do the sobbing for her. Adam Feldman

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'Love Will Tear Us Apart' – Joy Division

1. 'Love Will Tear Us Apart' – Joy Division

Sting gurgled, ‘If you love somebody, set them free’, and Bono wailed, ‘I can’t live with or without you.’ But neither of them got close to the exhausting, depressive reality of a tortured love affair. Their lyrics never fully summed up the paradox of attraction and repulsion, or the bittersweet pang of nostalgia that comes when something beautiful is dying. They were not, in other words, Ian Curtis.

The lead singer of seminal Manchester band Joy Division, Curtis was one of indie rock’s greatest losses – a troubled genius who let his shyness fall away onstage, but lived his personal life in quiet agony. ‘Love Will Tear Us Apart’ is Curtis at his most melancholic, and the ultimate chronicle of a relationship’s breakdown.

‘When routine bites hard / And ambitions are low / And resentment rides high / But emotions won’t grow / And we’re changing our ways / Taking different roads…’ The lyrics are ostensibly about Curtis’s relationship with his wife, Deborah, but they also refer to the inner rifts that contributed to his fragile psychological state and his eventual suicide in May 1980 – a mere five months after this track was recorded. For listeners, though, its eternal chorus – ‘But love, love will tear us apart again’ – says everything there is to say about the mixed pleasure and pain of being in thrall to another human being.

The music is post-punk at its minimal best, a sparse synth hook adding a touch of optimistic light to the shade of Curtis’s themes. It is, without a doubt, the best break-up song ever created: not just a ditty about dwindling affections, but a searingly precise evocation of human fragility. We are simple beings, it seems to say, made and broken by small moments, and powerless against the tide of our own emotions. Jonny Ensall

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