20. Gang Starr

Ex Girl to Next Girl (1992)

Hip-hop isn’t big on romantic heartbreak, but this is a particularly fine example. There’s a lot of bragging from Guru about how he’s so inundated with offers since his ex packed him in that she’s probably jealous. But somehow, you get the sense he’s 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 there’s something very grownup about this gorgeous forgotten single, a favourite of the late Lou Reed. Lillian Leach’s 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 Rain’s climax comes with a incredible spoken-word section, in which Juice threatens to “do a Rambo” on his love rival, but reconsiders: “I don’t wanna mess up this $37,000 lynx coat.”

17. The Left Banke

Walk Away Renée (1966)

The Four Tops’ famous cover amps up the emotions, but the Left Banke’s 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 Heart’s 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 there’s something very real and affecting about the emotions in Say Hello, Wave Goodbye. The icy synths and outpouring of lyrical bile don’t 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 it’s 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 didn’t have the decency to change the sheets”) – When You Were Mine’s 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

You’re So Vain (1972)

The mystery over its subject’s identity tends to obscure what a beautifully poised breakup song You’re 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”, there’s a weird, undimmed affection about the way she depicts him.

11. Yeah Yeah Yeahs

Maps (2003)

There’s almost nothing to Maps – a spindly guitar part, thumping drums, 10 lines of stark lyrics – and yet it’s incredibly potent and affecting: the quiet desperation of the endlessly repeated “They don’t love you like I love you”, the way Karen O’s 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 you’re 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 someone’s darkest moments, it’s 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 party’s parent. Behind Ms Jackson’s singalong chorus lurks a witty, complicated song that brilliantly covers a gamut of emotions while trying to explain what went wrong. It’s variously melancholy, angry, charming, exasperated and fatalistic. “You can plan a pretty picnic / But you can’t 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 Harley’s fabulously bitter recounting of Cockney Rebel Mark 1’s split. In the pantheon of screw-you-for-quitting songs – home to John Lennon’s How Do You Sleep? and Destiny’s Child’s Survivor – it reigns supreme, not least because it sets its spite to such sunny, charming music.

7. Etta James

I’d Rather Go Blind (1968)

On stage, James could stretch I’d 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, I’m so moving on” – complete with chorus designed for the recently dumped to bellow defiantly, gleefully along to.

ABBA. Photograph: Olle Lindeborg/EPA

5. ABBA

The Winner Takes It All (1980)

Featuring one of the great opening lines – “I don’t want to talk,” it protests, like a drunk in a bar desperate to spill their story – The Winner Takes It All’s gleaming pop perfection conceals real psychodrama: a woman, Agnetha Fältskog, singing lyrics by her ex-husband, Björn 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 Carpenter’s 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: “I’m 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

It’s 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 It’s 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.