Best Breakup Songs: 10 Classic Salves For Broken-Hearted Lovers

9: Sinéad O’Connor: Nothing Compares 2 U (1990)

A melancholic ballad originally written by Prince for his mid-80s side project The Family, Nothing Compares 2 U became a hit in the hands of Irish songstress Sinéad O’Connor, who released her own version of the song in January 1990. Summoning all the pain of an abandoned lover, O’Conner’s single was boosted by a memorable music video in which she delivered her despair directly to the camera, singing tearfully over broodingly stark instrumentation. “As far as I’m concerned,” O’Conner later reflected, “it’s my song.”

8: Crosby, Stills & Nash: Suite: Judy Blue Eyes (from ‘Crosby, Stills & Nash’, 1969)

With its luscious vocal harmonies, the seven-minute Suite: Judy Blue Eyes was one of the most painfully honest songs Crosby, Stills & Nash ever cut. Written and arranged by the supremely gifted Stephen Stills, it sees the songwriter reflect on his floundering relationship with Judy Collins, admitting that “it’s getting to the point where I’m no fun anymore”, and reaching the realisation that it’s all over. A beguiling expression of heartfelt recognition, Suite: Judy Blue Eyes peaked at No.21 in the US in 1969 and remains one of the best breakup songs of any era.

7: Fleetwood Mac: Go Your Own Way (from ‘Rumours’, 1977)

The ultimate breakup anthem, Go Your Own Way sees Fleetwood Mac singer Lindsay Buckingham cathartically lambast his former lover and fellow-bandmate Stevie Nicks for the downfall of their relationship. Rightly or wrongly, the story behind this soft-rock classic has already passed into rock’n’roll legend, with Buckingham’s bilious kiss-offs brilliantly capturing the bitterness of a spurned lover (“Shacking up is all you want to do”). An unbridled psycho-drama in song, Go Your Own Way reached No.10 in the US and, as the lead single from their unstoppable Rumours album, marked Fleetwood Mac’s ascent into the big leagues.

6: Harry Nilsson: Without You (from ‘Nilsson Schmilsson’, 1971)

Released by Los Angeles-based singer Harry Nilsson, Without You became a US No.1 thanks to its sorrowful Beatles-esque melody, soaring orchestration and dispirited lyrics (“I can’t live if living is without you”). Though it was originally written by Pete Ham and Tom Evans of 70s rock group Badfinger, Nilsson’s definitive cover quickly became regarded as one of the best breakup songs of all time. Famously leading to yet another chart-topping cover by Mariah Carey in 1993, Without You has since soundtracked many a lonely night.

5: Pet Shop Boys: Always On My Mind (single A-side, 1987)

Taking an Elvis Presley song and transforming it into a synth-pop tour de force, Neil Tennant and Chris Lowe took Always On My Mind to the UK Christmas No.1 spot in 1987, gifting us one of the best Pet Shop Boys songs in the process. Previously a US hit in 1982 for Willie Nelson, Tennant described the lyrics as “a typical country music sentiment, really – that the man should be a bastard”, capturing the self-recrimination of a broken-hearted ex-boyfriend pondering the one that got away.

4: Carole King: It’s Too Late (from ‘Tapestry’, 1971)

What makes Carole King’s It’s Too Late so refreshing is that it lacks the bitterness that characterises some of the best breakup songs. Reflecting on the end of her marriage to fellow-songwriter Gerry Goffin, King worked with lyricist Toni Stern to craft a piano ballad that expresses a woman’s desire to move on after acknowledging that it’s too late to reignite the dying embers of romance (“Somethin’ inside has died/And I can’t hide and I just can’t fake it”). A highlight from Carole King’s debut solo album, Tapestry – itself one of the best breakup albums in history – It’s Too Late sailed in at No.1 in the US and endures as one of the greatest reflections on a breakup ever written by a female songwriter.

3: Bob Dylan: Tangled Up In Blue (from ‘Blood On The Tracks’, 1975)

As Bob Dylan’s marriage to Sara Lownds was reaching its end, the poetic singer-songwriter poured all his marital woes into Tangled Up in Blue, a near-Shakespearean narrative song that tells the story of a relationship coming to a close. From parting ways (“Split up on a dark, sad night/Both agreeing it was best”) to relearning how to be alone (“The only thing I knew how to do/Was to keep on keepin’ on like a bird that flew”), it’s a true masterpiece from a skilled storyteller. Dylan often introduced the song during live shows by saying it took him “ten years to live, and two years to write”, so there’s little doubting Tangled Up in Blue was an artful reflection on his own experiences, easily making it one of the best breakup songs ever written.

2: Prince: Purple Rain (from ‘Purple Rain’, 1984)

Widely assumed to be lamenting the breakdown of a relationship (“I never wanted to be your weekend lover/I only wanted to be some kind of friend”), but also a song with its own undeniably spiritual overtones, the eight-minute power ballad that became the title track to Prince’s Purple Rain album is a gospel-infused mix of apocalyptic imagery and melancholic weariness that lives on as one of the best Prince songs of all time. A searing showcase of Prince’s exemplary guitar playing and his undoubtedly iconic voice, Purple Rain is an abstract and tear-jerking expulsion of Prince’s pent-up romantic frustrations which concludes that both lovers should go their separate ways (“It’s time we all reach out for something new – that means you, too”).

1: Joy Division: Love Will Tear Us Apart (single A-side, 1980)

When Joy Division frontman Ian Curtis wrote Love Will Tear Us Apart, his marriage to his wife, Deborah, was under strain, compounded by the strains of touring, Curtis’ personal struggles with epilepsy, and his affair with music promoter Annik Honoré. The song poetically captures the deep regret that comes with realising the end of a relationship is nigh (“When routine bites hard/And ambitions are low/And resentment rides high/But emotions won’t grow”). Sadly, unable to cope with his mounting pressures, Curtis committed suicide in May 1980. Peaking at No.13 in the UK following his death, Love Will Tear Us Apart remains the post-punk poet’s epitaph for a heart ripped asunder by a pain that cannot be cured, and it deservedly tops our list of the best breakup songs of all time.

Worn-out by all the melancholy? Cheer your hear with our pick of the best love songs ever.