50. 'Fuck You' – Cee-Lo Green
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Heaven knows you’re miserable now – so you may as well enjoy it with the best break-up songs ever made
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
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 WertheimerListen to 'Train in Vain' on YouTube | Buy this song on iTunes
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
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
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
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
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
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
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
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
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
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
From one of rock’s most painful break-ups came one of rock’s greatest break-up songs. The fallout from Lindsey Buckingham’s split with Stevie Nicks in 1976 may have made the recording of ‘Rumours’ a living hell for its creators, but who cares? It spawned one of the most defiant and furious songs of a generation. No pain, no gain. Oliver Keens
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
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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