The 50 greatest breakup songs of all time

On this stunner off 1968’s Tell Mama, James claims she’d prefer never being able to see again than watch her love walk away. What’s more, she's helpless: She notices the way her man is chatting up another girl and knows right then and there that, no matter how much she cares for him, it’s all over. Throw that sentiment over a simple chord progression that builds beautifully with horns, an organ, backing vocals and a heart-melting performance by James, and you've reached timeless soul perfection.  

Gotye might have scored a hit with the song by the same name, but Gotye doesn’t hold a flame to the heartbroken depths of Elliott Smith. Nobody does. The late-great Smith might have sung, ‘So when I go home, I’ll be happy to go / You’re just somebody that I used to know," but he wasn’t fooling anyone: This bare-bones, beautiful track is all about full-on heartache, albeit of the dismissive, fuck-you-I'm-fine variety. (For evidence, just skip to two songs later on Figure 8, ‘Everything Reminds Me of Her.’)   

Dolly Parton wrote and recorded this song in 1973 as a rueful envoi for her mentor and champion, Porter Wagoner, 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.  

Over a swelling, slow and deliberate melody, the Empress of Soul calmly and painfully recounts the end of her relationship in this heartbreaker. The song is an autopsy of a dead union as told from the perspective of a woman who has realized that love alone can't save a relationship that's gone toxic. ‘Farewell, my love, goodbye’ she belts out at the end, with the Pips' trademark echo of the phrase lingering in the ether like the soulful moans of a lovelorn ghost.

Love crashes into a wall – specifically, producer Phil Spector’s trademark ‘Wall of Sound’ – in this blue-eyed-soul lament, the 20th century’s most-played song on radio and TV. Cowritten by Spector and Brill Building hit makers Barry Mann and Cynthia Weil, the song begins with a sharp observation (‘You never close your eyes anymore when I kiss your lips’) that leads 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. 

Adele basically wrote the book on tear-soaked breakup ballads, and her catalog plays out like a musical tour through the stages of grief. ‘Someone Like You,’ however, is Adele at her most defeated and desperate as the singer's attempt at reconnecting with a lost love meets the hard wall of reality: He's now moved on. Yes, it's a little stalkery – especially as a double feature with ‘Hello’ – but it's also devastating: This is the scene in the movie where the hero chases her loved one on the train platform. Only in this movie, she's left standing, alone, in the rain as he rides off into a separate happy ending.

On the original cut of Red, ‘All Too Well’ was a torch song about young love gone sour. But when a post folklore Taylor revisited the album as an older and wiser songwriter in 2021, she ditched the torch in favor of a flamethrower. Clocking in at a breathless 10 minutes, the new version of ‘All Too Well’ finds Swift’s animosity over the heartbreak endured when she was 21 curdled into righteous resentment as she goes into extreme detail about her former beau’s duplicitous charms, manipulations and deceptions. In extending the song, Taylor transformed a fan favorite into a haunting masterpiece, and while she’s never confirmed who it’s about, it’s probably an awkward time to be an actor whose name rhymes with ‘rake spillin’ ball.’

The late singer-songwriter crooned plenty about addiction, depression and heartbreak, but nowhere more brutally than in this moody torch song, which gave its title to her 2007 album. Winehouse penned this hit single about her falling back into bad habits after her very public break with husband Blake Fielder-Civil. The gloomy repetition of the word black during the bridge is the sound of a spiral into darkness – albeit a funky one.  

Smokey might, indeed, ‘be the life of the party,’ but ‘deep inside [he's] blue,’ people. As with the best soulful weepers, ‘Tracks’ beautifully and economically articulates the pain of missing the one that got away. This summer-of-’65 staple – a cocktail of Smokey’s golden voice, swirling strings and horns, and a sing-along-worthy chorus – rings just as true today.  

‘Doo Wop (That Thing)’ may have been the flagship single from Lauryn Hill’s post-Fugees solo debut – 1998’s multi-Grammy-winning The Miseducation of Lauryn Hill – but it was the languid, lovely ‘Ex-Factor’ that rocketed the disc into the realms of extraordinary. Perfectly piquant down to the name of the song, ‘Ex-Factor’ longs for things to be different while knowing they can’t be, ringing with frustration (‘I keep letting you back in’) but humming with a love that refuses to fade. 

Whether she’s snarling at a former Full House star is irrelevant: Alanis’s searing, angry breakout is a primal scream of a scorned lover, and lines like ‘And every time I scratch my nails down someone else’s back I hope you feel it’ are relatable to anyone who's ever wanted to set fire to an entire relationship and watch it burn. 

Carole King’s era-shaping 1971 album, Tapestry, was in some sense a declaration of independence from Gerry Goffin, her former husband and songwriting collaborator. The album’s first single, ‘It’s Too Late,’ treats the end of a once-cherished relationship with bittersweet maturity, strength and striking lack of recrimination: ‘Still I’m glad for what we had / And how I once loved you.’ It’s a song about being realistic about the end – a sentiment made all the more moving by its initial pairing, as a single, with the tremblingly erotic ‘I Feel the Earth Move.’

The enduring force of the Yeah Yeah Yeahs’s most classic song lies in its expression of the inexpressible: the pithy, repetitive lyrics (‘Oh say, oh say, oh say... wait’) capturing that tongue-tied desperation between denial and acceptance. And as if Karen O’s weepy performance in the music video wasn't already affecting enough – the singer revealed that the tears were entirely genuine, motivated by her then-boyfriend (for whom she wrote the song) showing up to the shoot. 

Following your breakup with a hit single thanking each and every one of your past flames for the lessons learned from those relationships? The phrase ‘above it’ hardly seems sufficient for this refreshingly resentment-free ode to moving on. Ariana teaches us all what it means to go out with grace on this suprise-release earworm that’s packed with a surprising amount of wisdom. 

Over and again, whether hopeful or heartbreaking, Otis Redding’s exquisite love songs bring us to our knees, like this title track off the soul icon’s 1964 debut album for Stax Records subdivision Volt (which also includes the imploring ‘These Arms of Mine’). If you’re really in the mood to wallow, mourn the fact that Redding perished in a plane crash at age 26, just three days after recording ‘Dock of the Bay.’

Is there any song that combines female empowerment and discofied schmaltz with the same efficacy as Gloria Gaynor’s ‘I Will Survive?’ Probably not: 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’ sang over a soaring melody accented by horns and strings galore, this is the epitome of disco-ball empowerment 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.

Look, just because you’ve had your heart broken, it doesn’t mean that your mojo has to wilt away and die too – and the Reverend Al is here to spell that out via his definitive 1972 version of the Bee Gees cut. He aches just like you, but his hope hasn’t died  – ‘Please help me mend my broken heart / And let me live again’ ) – and Al’s signature slow, sensual soul arrangements prove that it's not just his heart that’s stirring. 

Jakob Dylan once said that listening to his father’s 1975 album, Blood on the Tracks, was like listening to his parents fighting. You can hear why on its opening track, ‘Tangled Up in Blue’ – a song that feels lived-in, true and intimate, and at the same time assumes an Odyssean quality. Inspired by Dylan’s split from his wife Sara, the song finds our narrator caught between throw-in-the-towel resignation and deep, soul-shuddering longing: tangled up in blue.

Troubadour Cohen has many a song in his arsenal to reduce grown adults to pathetic wistfulness, but this 1967 beauty is the most effective of them all. Its setup is simple – two lovers remember the happy times even as they part, via Cohen’s sweet, sad lyrics: ‘You know my love goes with you as your love stays with me / It’s just the way it changes, like the shoreline and the sea.’ What makes it a classic, however, is how upbeat Cohen’s picked guitar, mouth harp and evocative similes feel against the reality of the situation, deftly demonstrating that losing someone can be painful but cathartic.

The Destiny's Child songbook is a bible for the woman looking to keep her man on his toes. Just in case ‘Bills, Bills, Bills,’ ‘Say My Name’ and ‘Survivor’ didn't send a clear enough message, Beyoncé reiterated her ‘Don’t get too comfortable’ party line on this, the ultimate kick-you-to-the-curb anthem. The singer doesn’t sound the slightest bit perturbed as she shoos a disappointing lover out of her crib, advising him that he’ll find his worldly possessions ‘in a box to the left.’

It’s been a hit for other artists – notably Elvis Presley and the Pet Shop Boys – but ‘Always on My Mind’ has never packed more wallop than in Willie Nelson’s recording, the title track of his eponymous 1982 album. Humble and sincere, Nelson’s plea for forgiveness exudes the quiet wisdom of genuine contrition: Having finally opened his eyes, he allows himself to hope that they can still make contact.

Roy Orbison’s 1961 ballad is sensitive almost to a fault: the confession of a total bawler, reduced to tears even by touching the hand of the woman who broke his heart. But the emotion soaked into Orbison’s rich, quavering voice is offset by the singer’s disciplined, deadpan cool. Even when baring his sobbing soul, he somehow seems unflappable. 

This one from 1996’s Tragic Kingdom, which Gwen Stefani penned in response to her breakup with bandmate Tony Kanal, became the band’s most successful international single – and a rallying cry for lovelorn souls the world over to go right ahead and bury their head in the sand. 

Though this song was originally sung by Tommy Hunt in 1962 (and has since been covered by myriad musicians, including Dusty Springfield, Dionne Warwick, Isaac Hayes and Elvis Costello), no one has been able to capture the desperation – and frustration – behind the lyrics quite like Jack White. Recorded for the 2003 White Stripes release Elephant, this rock & roll version is perfect for the transition from heartbroken to pissed off.  

Always pushing his liver and vocal cords to the limit, Nilsson injected histrionics and heart into the songs he covered as if it were HGH. His take on Randy Newman’s ‘Living Without You’ is downbeat perfect. Fact: It is impossible to listen to this Kleenex-consuming epic without balling your hands into fists and mock-karaokeing along. Next song on the album? ‘Coconut.’ Drink the pain away.

A broken heart isn't just for those who've been broken up with – as ‘River’ attests. It's a breakup 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.

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 (which made an 11-minute version for its 1970 album Cosmo’s Factory) and claymation group the California Raisins. (Grapevine, raisins – see what they did there?) But nobody will ever match Marvin’s signature mix of vulnerabilty, indignation and pain.

Unlike Gladys, the Philly hitmakers simply can’t let go of the relationship they know is inevitably ending. The worst part is, after all the soulful pleas for things to go on, one gets the impression that the quartet is very much singing to somebody who’s already turned their back to walk into the sunset. 

This admonishing ode to Caroline appeared on Andre 300’'s half of Outkast’s 2003 double album, Speakerboxxx/The Love Below. It quickly achieved anthem status, thanks in no small part to Andre’s unapologetically frank (if a bit misogynistic) lyrics. Let’s be honest, sometimes cuties get away with bad behavior, but there are limits, and when your love interest crosses them, ‘Roses’ is the perfect way to tell them to piss off.

A classic in the genre of Songs to Cry to in Clubs, this 1988 electrodisco anthem tells the tale of a cheating heart haunted by its infidelity. ‘Footsteps on the dance floor / Remind me, baby of you / Teardrops in my eyes / Next time, I’ll be true.’ This silky cut comes from Cecil (brother of Bobby) Womack and his wife, Linda – a formidable musical partnership throughout the ’80s and ’90s. This is their biggest and best hit, however, and responsible for plenty tear-stained dancing shoes over the years. 

Prog-popstress Imogen Heap toes the line between poignantly lachrymose and sickeningly maudlin – so it’s unsurprising her most heartachey song was immortalized in the climactic scene to a season of The O.C.. From there, the indie tune took a viral turn, rocketing from an SNL Andy Samberg sketch straight into the top charts by-way of a Jason Derulo sample. That is to say: if these forlorn folktronica vocal harmonies are sad enough for the cast of The O.C., SNL and Jason Derulo, they’re sad enough to soundtrack your boring breakup. 

With an Aphex Twin sample, West balanced anger, pain and smartassery like no other MC can. It’s touching. That is, if you turn it off before Chris Rock comes in for the perplexing coda, exclaiming, ’This is some Cirque du Soleil pussy now!’ for reasons unknown. By the next album, Yeezus would be a married man, grudge-rapping about fisting and ejaculating on fine fur coats before eventually finding Jesus. 

The 1960s songwriting team of Burt Bacharach and Hal David found their perfect interpreter in Dionne Warwick, whose breezy style made the duo’s character-driven, rhythmically challenging tunes sound deceptively simple. In 1964's ‘Walk on By,’ one of her first Bacharach-David hits, Warwick teases out the smooth dignity in a song about the pain of rejection. 

Queen of '90s R&B heartache, Toni Braxton delivered more than just another sad love song when ‘Un-Break My Heart’ hit the airwaves in 1996. A mélange of Spanish guitars and Braxton’s sultry contralto vocals, the Grammy-winning single builds a quiet storm with a dramatic crescendo as Braxton pleads with her ex to rewind their doomed relationship back to happier times. If the song’s video is any indication, those happier times included playing Twister and sharing a shower with hunky model Tyson Beckford. So, yeah, we feel ya, Toni.

Who hasn’t been faced off of rosé, drunk dialing the one that got away? In the lead single from 2011’s Take Care, the Toronto hip-hip lord lays bare his romantic struggles over a stripped-down, wafting beat. At the time, it cemented Drake’s status as the reigning king of emo rap.

From one of rock’s most painful breakups came one of rock’s greatest breakup 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. 

More than a billion YouTubers have dropped their jaws at the Terry Richardson–directed video for Miley Cyrus's power ballad, in which a naked Cyrus straddling a massive steel ball. All snickers and parody videos aside, the track stands on its own as essential listening for dumpers and dumpees who have gone full-tilt into relationships and wound up emotionally demolished. And the racy video antics? Well, as BFF Lesley told us long ago, she’s just being Miley.

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 Paris's Parc de Saint-Cloud, was cited by Miley Cyrus as the inspiration for her 2013 ‘Wrecking Ball’ video. It can’t be denied that three decades later, O’Connor’s wrenching rendition still packs a punch.  

Like the haunted mirror image of ‘You Make My Dreams’ – or perhaps a follow up after the dream ended – ‘She's Gone’ proves that even on the yacht of life, stormy skies will rock your boat. 

The penultimate track on TLC's lauded sophomore effort finds the R&B high priestesses telling possessive lovers to shove off over a groovy flip of Jean Knight’s ‘Mr. Big Stuff.’ The album, CrazySexyCool, went diamond, rocketing Tionne ‘T-Boz’ Watkins, Lisa ‘Left Eye’ Lopes and Rozonda ‘Chilli’ Thomas into superstardom. Any time your paramour has you feeling a little claustrophobic, just remember Left Eye’s mantra: Erase, replace, embrace, new face.

What does a grime break-up song sound like? Pair OG grime pioneers Ruff Sqwad with the legendary Eskiboy and you’ve got yourself a break-up banger. Rapping over Ruff Sqwad’s original ‘Together’ (which samples the very familiar guitar rift from the Police’s ‘Message in a Bottle’), Wiley teases repeatedly with the rhetorical question, ‘(When we gonna) be together?’ He fills in his verses with strong punches at his ex-lover, providing the harsh reality of things and quickly becoming his own hype man as he promises to only do better for himself. Listen to Wiley: Don't wallow in self-pity. 

This devastating torch song was written for Ella Fitzgerald in 1953, but Julie London managed to release it before the Queen of Jazz was able to get a version out. It became London’s signature song: Backed by a late-night thrum of guitar and bass that teeters ambiguously between the minor and major keys, her hushed vocals waver between tender, haughty and devastated. 

You may hate American Idol. You may hate pop. You may hate it when people use u instead of you. But here’s the deal: You may also really hate your ex. And this song (off of Clarkson’s 2004 album, Breakaway) is so goddamned catchy, you can’t not belt out the chorus every time – with feeling.

What the hell does an 11 year old know about loss? With a tip of his giant purple pimp hat, Michael sang this Motown peak with a mile-wide smile on Ed Sullivan in ’69. Still, the kid sold it like nobody else, over chords that rise and fall like a roller coaster. And nothing hurts like first love.  

Most breakup songs are drenched in sadness. This peppy, almost painfully joyous dose of Swedish bubblegum indie finds Al Fakir positively elated to see his partner go, interlacing lines like ‘I’m so happy, cuz you are gone/You are gone, it makes me happy’ with sing-songy ‘la la la’ riffs, just to ensure the subject doesn't misinterpret the very-difficult-to-misconstrue lyrics. 

Lurking behind the glossy sheen and shimmering guitars of this 1997 global pop hit is the age-old story of a relationship gone sour. ‘Torn’ was originally recorded by American alt rockers Ednaswap, but saucy Aussie Natalie Imbruglia’s rendition perfectly encapsulates the unhappy transition from honeymoon optimism to the realization that ‘Illusion never changed  into something real.’ Seriously, we totally hate it when that happens.

RIP to the Biz, whose most famous hip hop track found him spinning a lovely, tragic tale about a girl named Blah Blah Blah who plunked the big teddy bear directly in the friend zone, only to break his heart irreparably. Whether Blah Blah Blah thought of this as a breakup song is a Rashomon situation we'll alas never see, but Biz's pained delivery shows that regardless, the scars were everlasting. 

Men’s emotions can sometimes be harder to read than a pureed copy of Proust. In 2004, however, the Streets’a Mike Skinner just laid it right on the line. While Skinner’s verses found him crestfallen at having been chucked, it’s the choruses that made the tune so beloved, delivering man-to-man comfort and kindly reassurances that there are ‘plenty more fish in the sea.’

On this chaotic track from Franz's glam-infused debut, Alex Kapranos seems intent on breaking the Guinness record for most utterances of ‘goodbye girl,’ before snottily and dismissively transitioning to a chorus of ‘I’m cheating on you.’ It's a cruel kiss-off of a song where once can imagine a burned lover trying to sneak one last barb into a fight, only to cross the point of no return. 

If you don’t think this is a brilliant song, then it’s probably only because you’ve heard it way too many times. Cher’s (temporary) resurrection as a dance-pop diva in 1998 has raised plenty of hackles over the years – not least for its then-unprecedented use of Auto-Tune – but at its heart it’s simply a great breakup song in the air-punchingly empowered tradition of ‘I Will Survive’: ‘I’ve had time to think it through / And maybe I’m too good for you.’ When we’re going through a rough time, we could all use a bit of that attitude.