The 20 greatest breakup songs ever ranked!

On the 40th anniversary of Gloria Gaynors I Will Survive topping the charts and as the UK blunders towards its own acrimonious divorce heres the definitive list of tear-stained stonkers

20. Gang Starr
Ex Girl to Next Girl (1992)

Hip-hop isnt big on romantic heartbreak, but this is a particularly fine example. Theres a lot of bragging from Guru about how hes so inundated with offers since his ex packed him in that shes probably jealous. But somehow, you get the sense hes protesting too much: Went home to see my mom and I saw you at the bus stop must I stop? I think not.

19. The Mellows
Smoke from Your Cigarette (1955)

Doo-wop tended to deal in teenage emotions, but theres something very grownup about this gorgeous forgotten single, a favourite of the late Lou Reed. Lillian Leachs vocal is limpid and beautiful, the tune sophisticated, the mood of resigned small-hours heartbreak all-enveloping. A miniature masterpiece.

18. Oran Juice Jones
The Rain (1986)

A fantastic record pitched between smooth 80s soul and the beatbox rhythms of hip-hop The Rains climax comes with a incredible spoken-word section, in which Juice threatens to do a Rambo on his love rival, but reconsiders: I dont wanna mess up this $37,000 lynx coat.

17. The Left Banke
Walk Away Rene (1966)

The Four Tops famous cover amps up the emotions, but the Left Bankes beautiful harpsichord-flecked original almost singlehandedly invents a particular strain of musical heartbreak, subsequently much deployed in indie music: sensitive, spurned narrator weeps discreetely, while stoically insisting all is fine.

16. Hank Williams
Cold Cold Heart (1951)

Blessed with a voice that just sounded like sadness, cursed with a disastrous love life, Hank Williams was made to sing songs such as this: austere, distraught and believable, never mawkish or overblown. He wrote dozens, all fantastic, but Cold Cold Hearts depiction of a disintegrating relationship is particularly vivid Love Will Tear Us Apart in a Stetson.

Marc Almond and Dave Ball. Photograph: Eugene Adebari / Rex Features

15. Soft Cell
Say Hello, Wave Goodbye (1981)

Any song that opens: Standing in the door of the Pink Flamingo / Crying in the rain lays itself open to accusations of camp, but theres something very real and affecting about the emotions in Say Hello, Wave Goodbye. The icy synths and outpouring of lyrical bile dont quite conceal the sadness at its core.

14. Bob Dylan
If You See Her, Say Hello (1975)

Blood on the Tracks has a song for every stage of a breakup from spleen-venting bitterness to quiet reflection but this may be its saddest, loveliest moment: crushed, resigned, haunted by the past, still holding out a vague hope its not all over, but aware, deep down, that it is.

13. Prince
When You Were Mine (1980)

A very Prince-ish breakup song he is particularly outraged that he used to let her wear all his clothes and at her lack of hygiene (You didnt have the decency to change the sheets) When You Were Mines taut, brilliant new-wave strut is the pouting, tough counterpart to the inconsolable Nothing Compares 2 U.

Carly Simon. Photograph: RB/Redferns

12. Carly Simon
Youre So Vain (1972)

The mystery over its subjects identity tends to obscure what a beautifully poised breakup song Youre So Vain is. She has clearly had enough of his smug, philandering bullshit, and is warning others off, but, from the opening murmur of Son of a gun, theres a weird, undimmed affection about the way she depicts him.

11. Yeah Yeah Yeahs
Maps (2003)

Theres almost nothing to Maps a spindly guitar part, thumping drums, 10 lines of stark lyrics and yet its incredibly potent and affecting: the quiet desperation of the endlessly repeated They dont love you like I love you, the way Karen Os voice shifts from an intimate murmur, cracking as she sings: Please stay. Inspired by her boyfriend going away temporarily, it feels like for ever.

10. Elvis Costello
I Want You (1986)

Some breakup songs help when youre in the romantic doldrums. I Want You just seems to make matters infinitely worse: its depiction of jealously and obsession is too angry, too disturbing, too self-flagellating. As a glimpse into someones darkest moments, its incredibly powerful, its impact heightened by the rawness of its one-take production. Amazingly, it was released as a single.

OutKast. Photograph: Jim Cooper/AP

9. OutKast
Ms Jackson (2000)

There are plenty of songs in which one party in a breakup addresses the other; fewer that address the other partys parent. Behind Ms Jacksons singalong chorus lurks a witty, complicated song that brilliantly covers a gamut of emotions while trying to explain what went wrong. Its variously melancholy, angry, charming, exasperated and fatalistic. You can plan a pretty picnic / But you cant predict the weather.

8. Steve Harley and Cockney Rebel
Make Me Smile (Come Up and See Me) (1975)

Not every great breakup song deals with romance, as evidenced by Steve Harleys fabulously bitter recounting of Cockney Rebel Mark 1s split. In the pantheon of screw-you-for-quitting songs home to John Lennons How Do You Sleep? and Destinys Childs Survivor it reigns supreme, not least because it sets its spite to such sunny, charming music.

7. Etta James
Id Rather Go Blind (1968)

On stage, James could stretch Id Rather Go Blind out to 10 minutes of extempore soul-bearing, but the simple, concise studio original is pretty much perfect. Exquisite tender/tough vocal, lyrics full of poignant detail: The reflection in the glass I held to my lips / Revealed the tears that was on my face.

6. Kelly Clarkson
Since U Been Gone (2004)

The 00s answer to I Will Survive, in that it turns a breakup into a badge of honour, something to express delight about I can breathe for the first time, Im so moving on complete with chorus designed for the recently dumped to bellow defiantly, gleefully along to.

ABBA. Photograph: Olle Lindeborg/EPA

The Winner Takes It All (1980)

Featuring one of the great opening lines I dont want to talk, it protests, like a drunk in a bar desperate to spill their story The Winner Takes It Alls gleaming pop perfection conceals real psychodrama: a woman, Agnetha Fltskog, singing lyrics by her ex-husband, Bjrn Ulvaeus, that ostensibly view their divorce and his new relationship from her perspective. Tell me does she kiss like I used to kiss you?

4. The Carpenters
Goodbye to Love (1972)

The creaminess of Karen Carpenters vocal notwithstanding, it seems astonishing that something this despairing and hopeless was ever classified as easy listening. The guitar solo is LA-sessioneer slick, but the lyrics starkly capture the point where romantic failure becomes a full-on existential crisis: No one ever cared if I should live or die all I know of love is how to live without it.

3. Gloria Gaynor
I Will Survive (1979)

Gloria Gaynor may have made better records, but I Will Survive is only overplayed because it connects with people so directly. The strings soar; the lyrics project defiance in the face of a controlling ex-partner who has made the mistake of chancing his arm again: Im not that chained-up little person still in love with you.

2. Marvin Gaye
I Heard It Through the Grapevine (1968)

The sound of someone trying and failing to keep calm in the face of mounting evidence his relationship is over, I Heard It Through the Grapevine is, musically, all cool control the single snare drum that opens it, the muted bass and electric piano playing the riff but vocally all anguish and urgency. The cumulative effect still floors you 50 years on.

Roy Orbison. Photograph: David Redfern/Redferns

1. Roy Orbison
Its Over (1964)

Originally an unconvincing rockabilly, Roy Orbison only hit his stride when he was allowed to unleash a melancholy that mapped out new, dark emotional territories for rock music. Certainly, no male performer had previously waded so deep into pain and vulnerability as Orbison did on In Dreams or Crying. But Its Over is his masterpiece, four inconsolable minutes during which stars cry, rainbows weep, golden days are sorrowfully recalled and drums beat out a leaden funeral march, before it all reaches a terrible climax, during which his voice rises to a desperate quiver, repeating the title as if misery is a kind of catharsis. Simultaneously melodramatic and relatable a bad breakup usually involves a degree of melodrama it has never been bettered.

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