Skip to main content

Enter your email below to be the first to hear about new releases, upcoming events, and more from Dig!

Please enter a valid email address
Please accept the terms
Best Breakup Songs: 40 Classic Salves For Broken-Hearted Lovers
List & Guides

Best Breakup Songs: 40 Classic Salves For Broken-Hearted Lovers

From cathartic ballads to musings on lost love, the best breakup songs face up to loneliness by coming to terms with the death of romance.


It’s never easy to wrestle with the grief and frustration of a relationship coming to an end. Whether it’s realising that your partner no longer loves you, or if you’re the one instigating the breakup, it almost always leads to someone getting hurt. By turns distraught and jaded, songwriters throughout the ages have found countless ways to channel their pain and turn fraught emotions into timeless songs that see the writing on the wall and capture the heart-wrenching loneliness and resignation that can come with it. Here, then, emerging from the ashes of many failed relationships, are our 40 best breakup songs…

Best Breakup Songs: 40 Classics For The Broken-Hearted

40: Cee-Lo Green: Fuck You (from ‘The Lady Killer’, 2010)

Hilariously childish and foul-mouthed, Cee-Lo Green’s retro-soul UK No.1 hit, Fuck You – also released as the more radio-friendly Forget You – is sung from the perspective of someone who’s seen another man driving around with his girlfriend, causing him to drop F-bombs with all the vengefulness of a military air strike. Realising that his relationship is over because his bank balance wasn’t up to snuff (“I guess he’s an Xbox, and I’m more Atari”), Fuck You was penned with Bruno Mars as a petty but joyous subversion of 60s pop innocence, trading doe-eyed sweetness for spiteful curse words as Green rails against his ex’s gold-digging antics. “It’s a fictitious account of love lost,” the singer said in an interview with NME. “But it’s a trial that we’ve all been through some time or another, and I think that’s why people can relate to it.”

39: Sandie Shaw: Tomorrow (standalone single, 1966)

While there are plenty of songs dealing with the hurt and immediate aftermath of a breakup, Tomorrow is unusual because it captures the sinking feeling of knowing you have to say goodbye (and feeling like an awful person because of it). In this entry among the best breakup songs, British pop icon Sandie Shaw is aware she’s been out of love for some time, but that her soon-to-be-ex-boyfriend hasn’t really done much wrong. “Our romance is through,” she sings, “though I don’t love him, I respect him, as before.” Tomorrow was part of a run of unusual and underappreciated Sandie Shaw songs in the mid-to late-60s, mostly forgotten in the wake of her victory in the 1967 Eurovision Song Contest. Shaw was even the first person to cover another vitriolic breakup anthem, Led Zeppelin’s Your Time Is Gonna Come, on her 1969 album, Reviewing The Situation.

38: Randy Newman: Living Without You (from ‘Randy Newman’, 1968)

Randy Newman is known for his lyrical sharpness and satirical delivery, and he brings these qualities to his woozy breakup song Living Without You. Fairground dizziness permeates the music, evoking the strangeness of suddenly being without someone who’s filled up the chambers of your heart. While the words are surprisingly straightforward compared to some of the best Randy Newman songs (“Baby it’s so hard, living without you”), Newman’s voice is anything but, suggesting defiance, defeat and despair – often at the very same time.

37: Robyn: Call Your Girlfriend (from ‘Body Talk’, 2010)

Women are so often pitted against one another in song and in life, and in breakup songs especially. One wins, one loses; competition and jealousy dominate. Yet Robyn takes a different tack. On Call Your Girlfriend, she expresses solidarity with the woman about to be ditched, even though she’s ostensibly her rival. Robyn suggests ways to be easy on the girlfriend, trying to make sure the unlucky lover doesn’t blame herself. Unique among the best breakup songs, it offers kindness in an appalling sea of hurt, and feels borne of real experience – or “love and life”, as Robyn said when asked about the song’s inspiration.

36: The Streets: Dry Your Eyes (from ‘A Grand Don’t Come For Free’, 2004)

Released as a single in July 2004, Dry Your Eyes is a lushly orchestrated acoustic-rap take on a breakup unfolding in real time, and it scored Mike Skinner’s era-defining UK hip-hop outfit The Streets a homeland No.1. With Skinner begging his girlfriend not to leave, and trying to convince her he’ll change, it’s a truly affecting expression of male vulnerability that ranks among the best breakup songs of the 21st century. With a friend stepping in during the chorus to offer consolation (“Dry your eyes, mate/I know it’s hard to take, but her mind has been made up/There’s plenty more fish in the sea”), Dry Your Eyes expresses the kind of sentiment most men have heard at some point in their lives, even if it feels like a cliché that doesn’t cut the mustard. “Everything’s just gone,” Skinner concludes at the end of what’s also one of the best Streets songs. “I’ve got nothing, absolutely nothing.” Give that man a hug.

35: Bonnie Raitt: I Can’t Make You Love Me (from ‘Luck Of The Draw’, 1991)

Written by songwriters Mike Reid and Allen Shamblin, the 1991 ballad I Can’t Make You Love Me was reportedly inspired by a news article in which a man appeared in court for shooting up his girlfriend’s car. Upon being asked by the judge what he’d learnt, the man replied: “You can’t make a woman love you if she don’t.” In the hands of blues singer Bonnie Raitt, I Can’t Make You Love Me peaked at No.18 on the US Hot 100, touching a chord in the hearts of men and women alike who can relate to the experience of reconciliation being just out of reach. “It was absolutely one of the most honest and original heartache songs I had ever heard,” Raitt said in an interview with The Los Angeles Times. “It was a point of view that I had been on both sides of, and it struck me deeply. I knew immediately I wanted to sing it.” Five years after its release, Prince tacitly approved I Can’t Make You Love Me’s place among the best love songs ever written, releasing a cover on his 1996 album Emancipation.

34: PinkPantheress: Break It Off (from ‘To Hell With It’, 2021)

PinkPantheress has emerged, just in the past couple of years, as one of the UK’s greatest contemporary lyricists, capable of encapsulating the unfiltered emotion of youth in short, almost fragmentary songs. First released anonymously on TikTok, Break It Off is a great example of her craft and a modern classic among the best breakup songs. PinkPanthresses’ voice is a shot of melancholy amid the music’s sensory overload of noisy breakbeats. As she said of her debut mixtape, To Hell With It (which featured this song): “I wanted to make everyone feel a bit depleted and sad.”

33: Madonna: Take A Bow (from ‘Bedtime Stories’, 1994)

Backed by a full orchestra, Madonna’s 1994 ballad Take A Bow saw her team up with R&B singer-songwriter Babyface for a show-stopping slow jam about closing the curtain on a relationship after realising her lover’s feelings aren’t genuine. Allegedly written about Madonna’s breakup with a famous actor, the song sees the “Queen Of Pop” confront the masquerade head on, feeling as if her lover’s been playing a role all along (“Say your lines, but do you feel them?/Do you mean what you say when there’s no one around?”). Opting to put an end to all the theatricality, Madonna chooses to skip to the end credits and move on with her life on this standout from her Bedtime Stories album (“You took my love for granted, why oh why?/The show is over, say goodbye”).

32: Ramones: Chain Saw (from ‘Ramones’, 1976)

Sometimes the pain in a breakup can circle right back to black humour, and that’s when you might reach for Ramones’ classic self-titled debut album and, in particular, Chain Saw. “Sittin’ here with nothin’ to do/Sittin’ here thinkin’ only of you” might be lyrics you’d find in any breakup song, but the fantasy that follows – an ex-girl being caught up in The Texas Chainsaw Massacre – is pure Ramonsian darkest comedy. Ramones felt themselves in a lineage with very early rock’n’roll, and this track, full of savage thrills, can help you forget your sadness in the buzz of a power tool.

31: Alanis Morissette: You Oughta Know (from ‘Jagged Little Pill’, 1995)

Channelling the ire of a scorned ex-girlfriend wishing ill on a man who left her for another woman, Canadian rock goddess Alanis Morrissette has never publicly acknowledged who You Oughta Know, from her Jagged Little Pill album, is actually about. Whoever inspired it was must have been nursing third-degree burns, with Morissette angrily pointing out how her ex’s new lover is just “an older version of me” and bitterly putting on a hex on him (“Every time I scratch my nails/Down someone else’s back, I hope you feel it”). One of the best Alanis Morissette songs, You Oughta Know peaked was issued as a double A-side with You Learn, making for the sweetest possible revenge when it peaked at No.6 in the US. “When I hear that song, I hear the anger as a protection around the searing vulnerability,” Morissette said in an interview with Spotify. “I was mortified and devastated. It was a lot easier for me to be angry and feel the power from that anger versus the broken, horrified woman on the floor.”

30: Gang Starr: Love Sick (from ‘Step In The Arena’, 1991)

Hip-hop duo Gang Starr, made up of DJ Premier and rapper Guru, create a frighteningly relatable short story of a couple’s breakdown on Love Sick. Guru doesn’t see what he does wrong when his girl objects to other women flirting around him, or when he eschews her company for friends; he finds her possessive, she finds his lack of consideration endlessly frustrating, and a breakup becomes inevitable. “Relationships can grip with the pain,” Guru raps, with grim understatement. The song’s promo video features Guru’s real-life girlfriend of the time, Tonya, something which DJ Premier remembers with affection. “Every video that [Guru’s] done about a girl, he’d always have his girlfriend play the role in the video,” he said in 2011. “In Ex Girl To The Next Girl [a track on Gang Starr’s 1992 album, Daily Operation], that was his ex-wife.”

29: No Doubt: Don’t Speak (from ‘Tragic Kingdom’, 1995)

Peaking at No.1 in both the UK and the US, No Doubt’s 1995 alt-rock anthem Don’t Speak sold over ten million copies in North America alone while tenderly exploring the dissolution of one of the most famous band relationships of the 90s. “I really feel that I’m losin’ my best friend/I can’t believe this could be the end,” frontwoman Gwen Stefani sings, reflecting on her breakup with the band’s bassist, Tony Kanal. Thankfully, the pair remained friends, proving that – in some cases – it’s possible for ex-lovers to remain on good terms. However, Kanal suggested that the song’s music video should subvert the idea that No Doubt had emerged from the situation intact. “We didn’t want it to be about a normal breakup,” Kanal said. “So we thought: What would be the saddest thing that could happen? The band splitting up? So that’s what the video’s about.”

28: Phil Collins: Against All Odds (Take A Look At Me Now) (standalone single, 1984)

Perfectly capturing the period of denial which follows a breakup, the 1984 power ballad Against All Odds (Take A Look At Me Now) sees Phil Collins confounded by the end of a relationship (“How can you just walk away from me?”) while admitting just how much his lover meant to him (“You’re the only one who really knew me at all”). What makes Against All Odds so refreshing among the best breakup songs is that, instead of shrinking into a corner, Collins resorts to winning his ex back, realising that he cannot live without her (“Take a good look at me now, ’cause I’ll still be standin’ here/And you coming back to me is against all odds/It’s the chance I’ve gotta take”). We never find out if the story has a happy ending, but the idea of not giving up on love is painfully relatable nonetheless.

27: Natalie Imbruglia: Torn (from ‘Left Of The Middle’, 1997)

Originally recorded by post-grunge band Ednaswap in 1995, it wasn’t until Natalie Imbruglia released a cover of Torn, in October 1997, that the song became a bona fide international hit. Easily one of the best breakup songs of the 90s, Torn captures the heart-shattering devastation of realising that the person you’re in love with may not feel the same way (“Well you couldn’t be that man that I adored/You don’t seem to know, or seem to care, what your heart is for”). Bristling with anxiety, Imbruglia’s voice truly cuts like a knife, capturing the vulnerability of being a prisoner of your own emotions. “I’m cold and I am shamed/Lying naked on the floor,” she sings. One of the best 90s songs, Torn could have been written for any one of us.

26: Carly Simon: You’re So Vain (from ‘No Secrets’, 1972)

Carly Simon’s legendary kiss-off to a preening ex-lover – a man who is constantly checking himself out in the mirror – is one of the most mysterious breakup songs in history. Was it about Mick Jagger? (Nope, apparently not.) What about Warren Beatty? Don’t look for answers from Simon herself, as she has consistently said she’d never kiss and tell – though she has left a few breadcrumb clues over the years, and Richard Perry, producer of Simon’s No Secrets album, has said he believes it’s about more than one person. “I was in love with a lot of men,” Simon told Uncut magazine in 2010. “I was definitely a romantic and my hopes were dashed. That led to the song.” Thankfully, You’re So Vain doesn’t really require anyone to know the real story. Ostensibly about a cocky love interest with playboy aspirations, the song could be about anyone who manipulates you and makes you feel special, only to disappoint you when it suits them. “Well you said that we made such a pretty pair and that you would never leave,” Simon sings. “But you gave away the things you loved, and one of them was me.” Ouch. What a douchebag. Or douchebags. Your guess is as good as ours!

25: Gloria Gaynor: I Will Survive (from ‘Love Tracks’, 1978)

Capturing the moment of epiphany which comes after nursing a broken heart for long enough, Gloria Gaynor’s 1978 disco favourite and LGBTQ+ anthem I Will Survive is one of the best breakup songs ever written. Embraced as a song of female empowerment, it’s sung from the perspective of a woman who is finally ready to move on from her ex, only to find him coming crawling to her door in an attempt to win her back. “Weren’t you the one who tried to break me with goodbye?” Gaynor recalls. “You think I’d crumble? You think I’d lay down and die?” Proving that the grass can, indeed, be greener on the other side of a breakup, I Will Survive has endured throughout the ages, standing the test of time as an ode to self-worth, inner confidence and how time can be a great healer. Let’s face it: sometimes you’re better off without him.

24: Otis Redding: Pain In My Heart (from ‘Pain In My Heart’, 1963)

One of the greatest soul singers of all time, Otis Redding scored his second Billboard Hot 100 success with the country-soul ballad Pain In My Heart, which peaked at No.61 in the US in February 1964. Articulating a feeling of deep anguish that men often find it difficult to speak about, the song is an incredibly moving expression of lost love that positively aches with longing among the best breakup songs (“Wake up restless nights/Lord and I can’t even sleep”). As the title track to Redding’s debut album, Pain In My Heart, the song introduced the world to the “King Of Soul”’s ability to channel the restlessness of inconsolable grief, rendered all the more poignant by the tossing’n’turning of Johnny Jenkins’ lead guitar riffs. It’s nothing short of exquisite.

23: Roxette: It Must Have Been Love (standalone single, 1987)

Believe it or not, Swedish pop-rock group Roxette originally released It Must Have Been Love as a Christmas song back in 1987. However, it wasn’t until the song was re-packaged as a gut-punching power ballad and included on the soundtrack to the 1990 movie Pretty Woman that it soared to No.1 in the US and No.3 in the UK. Full of soaring melodies and angelic vocals, It Must Have Been Love earns its place among both the best breakup songs and the best Roxette songs thanks to a sublime chorus which sees a love-struck Marie Fredriksson attempt to dust herself off after a failed romance (“It must have been love, but it’s over now”). Catapulting Roxette to unparalleled heights, this track was a karaoke favourite throughout the 90s, turning the dejectedness of heartbreak into a bona fide anthem.

22: ABBA: The Winner Takes It All (from ‘Super Trouper’, 1980)

Released amid divorce proceedings between ABBA songwriter Björn Ulvaeus and singer Agnetha Fältskog, The Winner Takes It All is a sweeping ballad that turns the real-life story of marital strife from within the group’s ranks into a gold-plated pop classic. “Björn wrote it about us after the breakdown of our marriage,” Fältskog admitted in an interview with The Mail On Sunday in 2013. “The fact that he wrote it exactly when we divorced is touching, really,” she explained. “It was fantastic to do that song because I could put in such feeling.” Peaking at No.1 in the UK and No.8 in the US, what makes The Winner Takes It All so emotional is the fact that fellow ABBA bandmates Benny Andersson and Anni-Frid Lyngstad were also going through a breakup at the same time, making the song a painfully honest reflection of the death throes of romance.

21: Coldplay: The Scientist (from ‘A Rush Of Blood To The Head’, 2002)

Reaching No.10 in the UK in November 2002, Coldplay’s evocative piano ballad The Scientist tells the story of a man of science who ponders life’s big questions but is mystified when it comes to heartbreak. “It’s weird that whatever else is on your mind, whether it’s the downfall of global economics or terrible environmental troubles, the thing that always gets you most is when you fancy someone,” frontman Chris Martin admitted. As one of the best breakup songs of the 2000s, The Scientist sold 1.2 million copies in the UK and captured the disconsolate melancholy at the heart of many of the best Coldplay songs (“Nobody said it was easy/It’s such a shame for us to part”).

20: Sinéad O’Connor: Nothing Compares 2 U (from ‘I Do Not Want What I Haven’t Got’, 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.”

19: 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.

18: Pet Shop Boys: Always On My Mind (standalone single, 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.

17: The Chantels: Maybe (from ‘We Are The Chantels’, 1958)

A song credited with kicking off the “girl group” sound of the 60s – where breakup songs were the genre’s bread-and-butter – Maybe saw The Chantels create the classic sound of teenage yearning. Sorrowful at the loss of a boy, the young vocalist Arlene Smith (who also, uncredited, co-wrote the song) has said she was singing much more from imagination than experience. “I tended to lean towards songs that had some sort of heartbreak, or some kind of sadness,” she explained in the 80s. “I was singing about the kind of love that I didn’t know. I loved my parents.”

16: Jimmy Ruffin: What Becomes Of The Brokenhearted (from ‘Jimmy Ruffin Sings Top Ten’, 1966)

Probably Motown’s bleakest offering, What Becomes Of The Brokenhearted became a transatlantic Top 10 hit for Jimmy Ruffin in June 1966. Venturing through “a land of broken dreams” after his lover abandons him, Ruffin sounds like a wounded soul searching for answers, but failing to find any deeper meaning to his plight. “Happiness is just an illusion/Filled with sadness and confusion,” he sings. Motown’s track record is so strong, any number of its tunes could claim a place among the best breakup songs, but with What Becomes Of The Brokenhearted the Detroit label excelled in capturing the bewilderment of those who simply cannot face a world without the one they love by their side.

15: 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.

14: The Supremes: Where Did Our Love Go (from ‘Where Did Our Love Go’, 1964)

Nobody gave voice to the innocence of teen romance better than Diana Ross And The Supremes. With Where Did Our Love Go, the Detroit-based girl group turned their attention to heartbreak, all set to an upbeat drum groove that underscores the monsoon of naïvety that rains down over the jilted lovers of the world (“Baby, baby, baby, don’t leave me/Ooh, please don’t leave me/All by myself”). Released in June 1964, this historic song peaked at No.1 in the US and No.3 in the UK, with Rolling Stone magazine ranking it among the 500 Greatest Songs of All Time in 2004. A dead cert in our list of the best breakup songs, Where Did Our Love Go remains a timeless eulogy to the bafflement of lost love.

13: 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.

12: Amy Winehouse: Back To Black (from ‘Back To Black’, 2006)

Featuring candid lyrics inspired by her breakup with boyfriend Blake Fielder-Civil, Amy Winehouse’s 2007 single Back To Black is a piano ballad par excellence. Not only is it imbued with the spirit of 60s R&B and soul music, but it also swirls with dark clouds of gloom and an almost funereal air of resignation. “Back To Black is when you’ve finished a relationship and you go back to what’s comfortable for you,” Winehouse told The Sun in 2006. “My ex went back to his girlfriend and I went back to drinking and dark times.” Truly deserving its place among the best breakup songs, Back To Back peaked at No.8 in the UK and has come to be embraced as a modern classic, particularly since Winehouse’s tragically early demise, in 2011, which saw her enter the notorious “27 Club”.

11: The Beatles: Yesterday (from ‘Help!’, 1965)

Waking in the middle of the night with a melody in his head, Paul McCartney sat at a piano by his bedside and wrote Yesterday for The Beatles as if he were overcome by a higher power. Since it felt more like a solo composition than a band effort, producer George Martin opted to drench McCartney’s tear-jerking acoustic ballad with violins and cello, perfectly framing the thought-provoking lyrics which told the story of a lover gone AWOL (“Yesterday/Love was such an easy game to play/Now I need a place to hide away”). Covered by some of the era’s biggest music icons, including Frank Sinatra and Marvin Gaye, Yesterday is now rightfully cherished as a modern standard among the best breakup songs, and it sounds just as magical as the day it was recorded.

10: 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.

9: Smokey Robinson And The Miracles: The Tracks Of My Tears (from ‘Going To A Go-Go’, 1965)

Smokey Robinson and his band, The Miracles, were one of Motown’s biggest hitmakers, and their 1965 single The Tracks of My Tears stands tall as a phenomenal work of melancholic genius among the best breakup songs. Giving the listener a glimpse into the soul of every man who hides behind a smile to mask his true feelings, it’s tinged with despair as Robinson sings about a someone who hides his heartbreak in plain sight (“Although I might be laughing loud and hearty/Deep inside I’m blue”). Reportedly taking him six months to write, The Tracks Of My Tears was a huge leap for Robinson, who beautifully lifted the mask on male vulnerability in order to reveal the hidden reality of a broken heart.

8: Joni Mitchell: River (from ‘Blue’, 1971)

Being lonely at Christmas can play havoc with the emotions, particularly if you’ve been dumped just before the festivities begin – so River, from Joni Mitchell’s 1971 album, Blue, cuts deep. Acknowledging that the breakup may have been partially her fault, Mitchell delivers a heart-rending piano ballad that reflects how loneliness often goes hand in hand with remorse (“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”). Ranking highly among the best breakup songs of all time, River flows on a combination of Mitchell’s beautiful voice and clever lyrical juxtaposition as she admits that hearing people “singing songs of joy and peace” only makes her want to skate away on a frozen river, making the heart swell with each listen.

7: 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.

6: The Doors: The End (from ‘The Doors’, 1967)

“It just started out as a simple goodbye song,” Doors frontman Jim Morrison said in 1969 of The End. “Probably just to a girl, but I could see how it could be goodbye to a kind of childhood. I really don’t know. I think it’s sufficiently complex and universal in its imagery that it could be almost anything you want it to be.” Ambitious in scope and wide-ranging in its subject matter, The End features some of the best Jim Morrison lyrics, and was inspired by – among other things – the singer’s breakup with his first serious girlfriend, Mary Werbelow. He reportedly told her, in 1968, that “The first three [Doors] albums are about you. Didn’t you know that?” Werbelow didn’t have the heart to tell him she had never listened to any of them.

5: 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”).

4: All Saints: Never Ever (from ‘All Saints’, 1997)

Written as All Saints’ Shaznay Lewis was trying to overcome heartbreak, Never Ever has proved to be one of the most relatable entries among the best breakup songs of all time. The stark vulnerability of the lyrics came directly from Lewis’ painful feelings. “I never believed that so much good could come out of a bad situation,” she said of the song’s success. The combination of All Saints’ vocals on Never Ever – particularly Nicole Appleton’s raw spoken intro, which was taken directly from the original demo recording – capture perfectly the confusion and distress that follows an unexpected ending.

3: Bill Withers: Ain’t No Sunshine (from ‘Just As I Am’, 1971)

With lyrics inspired by the characters of two wayward alcoholic lovers in the 1962 movie Days Of Wine And Roses, the timeless acoustic-soul ballad Ain’t No Sunshine was written by Bill Withers at the age of 31, when he was a factory worker making toilet seats for a living. Transforming the song into a meditation on a dysfunctional relationship in which breakups are regular (and often), Withers muses on whether the loneliness he feels is for good (“Wonder this time where she’s gone/Wonder if she’s gone to stay”) while contemplating on how this “can’t live her, can’t without her” scenario isn’t exactly a healthy way to live (“I oughta leave young thing alone/But ain’t no sunshine when she’s gone”). Peaking at No.3 in the US in July 1971, Ain’t No Sunshine proved that relationship-ending tiffs aren’t just one-time only affairs, and it continues to endure as one of the best breakup songs of all time.

2: Dionne Warwick: Walk On By (from ‘Make Way For Dionne Warwick’, 1964)

Devastating in its attempts to retain dignity in the face of despair, Walk On By is a Burt Bacharach and Hal David classic, sung by their greatest collaborator, Dionne Warwick. “I was dear, dear friends with both Burt and Hal,” Warwick said in 2014. “We depended on each other to bring to the table the expertise we each possessed. Hal David’s lyrics were the most incredible I’ve ever sung. And Burt created those intricate, but memorable, melodies. And I was the vehicle to bring all of that to the listeners’ ears.” Warwick, to this day, adores the song, which has become a byword for desperately faking nonchalance until you really get over someone: one of the very, very hardest post-break up illusions to maintain.

1: Joy Division: Love Will Tear Us Apart (standalone single, 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 relentlessness 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 heart with our pick of the best love songs ever.

Original article: 8 February 2022

Updated: 12 February 2023. Words: Luke Edwards | 10 February 2024. Words: Jeanette Leech

More Like This

Best Eric Burdon And War Songs: 10 Funk, Rock And Soul Classics
List & Guides

Best Eric Burdon And War Songs: 10 Funk, Rock And Soul Classics

From summery slow jams to pleas for peace, the best Eric Burdon And War songs offer grooves for the feet and messages for the mind.

Best Trevor Horn Productions: 10 Pioneering Songs That Shaped Pop Music
List & Guides

Best Trevor Horn Productions: 10 Pioneering Songs That Shaped Pop Music

From Seal to Yes and Pet Shop Boys, the best Trevor Horn productions changed the pop landscape in the 80s and beyond.

Sign up to our newsletter

Be the first to hear about new releases, upcoming events, and more from Dig!

Sign Up