The most devastating break-up songs of all time

Chances are, at some point in your life, you’ve made a playlist designed with a broken heart in mind. One of the very staples of modern music is the break-up song – some sassy, some celebratory, some wallowing in the pain – and it’s rare to find an artist without at least one in their arsenal. We’ve pulled together a list of some of the most heart-wrenching break-up songs ever written, all ready for the next time your heart gets shattered by the one you love.

Yeah Yeah Yeahs – ‘Maps’

Yeah Yeah Yeahs’ most emotional song is one to avoid when you’re feeling fragile – the despair in Karen O’s voice, coupled with that iconic video, is enough to tip the sturdiest of hearts over the edge.  

Killer lyric: “Wait, they don’t love you like I love you”

Rihanna – ‘Stay’

RiRi’s Mikky Ekko collab presented the idea of beginning to lose someone you thought could fix you, only to find they’re just as broken.   

Killer lyric: “Something in the way you move/Makes me feel like I can’t live without you” 

Adele – ‘Someone Like You’

The queen of tear-inducing ballads knocked it out of the park on this one, creating the perfect heartbreaker for when your ex is happily settled with a new lover. 

Killer lyric: “I hate to turn up out of the blue uninvited/But I couldn’t stay away, I couldn’t fight it/I had hoped you’d see my face/And that you’d be reminded that for me, it isn’t over”

Amy Winehouse – ‘Back To Black’

Overanalysing a relationship’s demise is a bad habit of the newly single and here Winehouse lets herself indulge, each scenario ending the same – with things over and her ex with another woman. 

Killer lyric: “We only said goodbye with words/I died a hundred times/You go back to her and I go back to black”

Joni Mitchell – ‘A Case Of You’

A break-up doesn’t necessarily mean giving up and letting go of someone. In this case, Mitchell’s ex has become such a part of her they’re “in her blood” and someone she’s built up a hardy tolerance to so she can enjoy them even more.  

Killer lyric: “You are in my blood like holy wine/You taste so bitter and so sweet/Oh, I could drink a case of you darling/And I would still be on my feet” 

Lorde – ‘Hard Feelings/Loveless’

It’s the specifics that make this standout from ‘Melodrama’ so heartbreaking, both incredibly particular but universally relatable. 

Killer lyric: “But I still remember everything/How we’d drift buying groceries, how you’d dance for me”

Lady Gaga – ‘Million Reasons’

Rumoured to be about her ex-fiancé Taylor Kinney, Gaga emotionally encapsulates when you really want something to work out and are willing to overlook all your problems if you can find just one good excuse.  

Killer lyric: “Lord, show me the way/To cut through all his worn out leather/I’ve got a hundred million reasons to walk away/But baby, I just need one good one to stay”

Joy Division – ‘Love Will Tear Us Apart’

The breakdown of a marriage sounds even more crushing when set to Joy Division’s cold, brittle post-punk. 

Killer lyric: “You cry out in your sleep, all my failings explored/And there’s a taste in my mouth as desperation takes hold/Just that something so good just can’t function no more”

Whitney Houston – ‘I Will Always Love You’

A karaoke classic, ‘I Will Always Love You’ waves goodbye to an ex as only a pop diva could – by belting out those emotions until everyone’s a mess.  

Killer lyric: “Bittersweet memories/That’s all I’m taking with me/So goodbye, please don’t cry/We both know I’m not what you need”

The Weeknd – ‘Call Out My Name’

There’s no worse feeling than not being wanted by the one you love, as Abel Tesfaye details on this piece of gloomy R&B. 

Killer lyric: “I want you to stay, even though you don’t want me” 

Leonard Cohen – ‘Chelsea Hotel #2’

Cohen’s fling with Janis Joplin might not have been the romance of the century, but his reflections on it were full of longing and vulnerability. 

Killer lyric: “Yeah, but you got away, didn’t you babe?/You just turned your back on the crowd/When you got away, I never once heard you say/I need you”

Bill Withers – ‘Ain’t No Sunshine’ 

Late soul icon Withers is stuck in a cycle on this heartbreaking classic, suggesting his girlfriend has broken up with him many times before when he sings: “Wonder this time where she’s gone/Wonder if she’s gone to stay”. 

Killer lyric: “Ain’t no sunshine when she’s gone/Only darkness every day”

Bon Iver – ‘Skinny Love’

You don’t need to hole yourself up in a cabin the woods to get over a break-up – just listen to the record Justin Vernon made during his own time in romantic self-isolation. 

Killer lyric: “And I told you to be patient/And I told you to be fine/And I told you to be balanced/And I told you to be kind/And now all your love is wasted”

St Vincent – ‘New York’

An ode to how a city changes post-breakup and seeing spectres of your old relationship on every street corner. 

Killer lyric: “I have lost a hero/I have lost a friend/But for you, darling/I’d do it all again”

No Doubt – ‘Don’t Speak’

Gwen Stefani and co.’s big hit is painful enough in its lyrics, but add in those big, juddering guitars that mirror stuttering tear-wracked sighs and it becomes overwhelmingly tragic. 

Killer lyric: “I really feel that I’m losing my best friend/I can’t believe this could be the end”

Dolly Parton – ‘Jolene’

Love isn’t neat and sometimes relationships can’t help but overlap. Dolly Parton took us into the mind of the one being left behind as she begged the other woman to do the right thing. 

Killer lyric: “He talks about you in his sleep/There’s nothing I can do to keep/From crying when he calls your name, Jolene”

Arctic Monkeys – ‘Love Is A Laserquest’

Alex Turner has written many a poignant lyric about love but this song is full of some of his best as he imagines a doomed relationship having a lifelong impact. 

Killer lyric: “When I’m pipe and slippers and rocking chair/Singing dreadful songs about summat/Will I have found a better method of pretending you were just some lover?”


READ MORE: 45 OF THE SADDEST SONGS EVER WRITTEN


The Cure – ‘Apart’

Unlike most love songs, this 1992 Cure track looks at the dissolution of a relationship from both perspectives, each as hopeless as each other. 

Killer lyric: “He waits to hear her say, ‘Forgive’/But she just drops her pearl-black eyes/And prays to hear him say, ‘I Love You’/But he tells no more lies” 

Etta James – ‘I’d Rather Go Blind’

Love can drive us to extremes and Etta James is proof, favouring never seeing again over being given the boot. 

Killer lyric: “I would rather go blind, boy/Than to see you walk away from me, child”

Bob Dylan – ‘If You See Her, Say Hello’

There’s no such thing as moving on for Dylan on this ‘Blood On The Tracks’ cut, as he promises listeners he’s never forgotten his lost love. 

Killer lyric: “We had a falling out, like lovers often will/And to think of how she left that night, it still brings me a chill/And though our separation, it pierced me to the heart/She still lives inside of me, we’ve never been apart”

Billie Eilish – ‘When The Party’s Over’

Like the aftermath of a party, Eilish knows the end of a romance is one characterised by loneliness and quiet, manifested here in her hushed delivery and creeping synths. 

Killer lyric: “Don’t you know I’m no good for you?/I learned to lose you, can’t afford to/Tore my shirt to stop you bleeding/But nothing ever stops you leaving”

The Beatles – ‘Yesterday’

There’s a reason why ‘Yesterday’ is the most-covered song in history – it’s a classic story of lost love and longing for a time when your heart didn’t ache. 

Killer lyric: “Suddenly/I’m not half the man I used to be/There’s a shadow hanging over me/Oh yesterday came suddenly”

Jeff Buckley – ‘Lover You Should’ve Come Over’

On this seven-minute epic, Buckley acknowledges his romantic failings but refuses to accept that a relationship is over, offering all he has for small moments with his love. 

Killer lyric: “My kingdom for a kiss upon her shoulder/It’s never over/All my riches for her smiles when I slept so soft against her”

The xx – ‘On Hold’

Sampling Hall & Oates doesn’t exactly scream heart-wrenching break-up song but trust us, this ode to finding out your relationship isn’t written in the stars is subtly crippling. 

Killer lyric: “Now you’ve found a new star to orbit/It could be love, I think you’re too soon to call us old/When and where did we go cold?/I thought I had you on hold”

Sinead O’Connor – ‘Nothing Compares 2 U’

The video for this Prince-penned hit is iconic because of its simple but visceral premise, and the powerful effect it and the track itself hold over those who come across it. 

Killer lyric: “It’s been so lonely without you here/Like a bird without a song/Nothing can stop these lonely tears from falling/Tell me baby, where did I go wrong”

Beck – ‘Lost Cause’

This 2002 song finds Beck ready to dump with partner, “tired of fighting” to keep a dying relationship alive. 

Killer lyric: “Baby you’re a lost cause/I’m tired of fighting” 

Toni Braxton – ‘Un-Break My Heart’

An R&B classic, ‘Un-Break My Heart’ is filled with yearning and a chance for a do-over, without all the tears and pain. 

Killer lyric: “Time is so unkind/And life is so cruel without you here beside me”

Bruce Springsteen – ‘I’m Goin’ Down’

The Boss narrates trying to keep a lover interested but battling a rapidly extinguishing spark that’s impossible to keep alight. 

Killer lyric: “I pull you close now baby, but when we kiss I can feel a doubt/I remember back when we started/My kisses used to turn you inside out”

The Streets – ‘Dry Your Eyes’

The whole song plays out across one final interaction, but goes into devastating detail to make The Streets’ most affecting song. 

Killer lyric: “I’m not gonna fucking just fucking leave it all now/Cos you said it’d be forever and that was your vow/And you’re gonna let our things simply crash and fall down?”

Blur – ‘No Distance Left To Run’

Written about the end of his relationship with Elastica’s Justine Frischmann, Damon Albarn is resigned to letting her move on. 

Killer lyric: “I hope you’re with someone who makes you feel/Safe in sleep, being tonight/I won’t kill myself trying to stay in your life/I got no distance left to run”

Harry Nilsson – ‘Without You’

‘Without You’ is a classic for a reason, Nilsson nailing that feeling of life being over in big wail-a-long choruses. 

Killer lyric: “I can’t live if living is without you/I can’t live, I can’t give anymore”

The Smiths – ‘I Know It’s Over’

Leave it to Morrissey to write the darkest break-up song of all, comparing being dumped to being put six feet under. 

Killer lyric: “Oh mother, I can feel the soil falling over my head/And as I climb into an empty bed/Oh well, enough said/I know it’s over, I still cling”

Lykke Li – ‘Sleeping Alone’

Over the course of ‘I Never Learn’, Lykke Li charts a break-up and, on its closing song, struggles to accept her new solo status.   

Killer lyric: “How can I get used to?/How can I forget you?/Will I get used to sleeping alone?”

Sharon Van Etten – ‘Your Love Is Killing Me’

If Etta James took things to extremes, SVE is off the scale with this desperate plea to call things quits. 

Killer lyric: “Break my legs so I won’t walk to you/Cut my tongue so I can’t talk to you/Burn my skin so I can’t feel you/Stab my eyes so I can’t see”

Feist – ‘Intuition’

Feist’s message on ‘Intuition’ is clear – going with your gut can work sometimes but you might find yourself wondering what could have been had you chosen a different path. 

Killer lyric: “And it’s impossible to tell/How important someone was/And what you might have missed out on/And how he might have changed it all/And how you might have changed it all for him”

The Velvet Underground – ‘Pale Blue Eyes’

Lou Reed wrote this jangly heart-melter about his first real love Shelley Albin – someone he’d try to get back with several times in his life but ultimately fail. 

Killer lyric: “Thought of you as my mountaintop/Thought of you as my peak/Thought of you as my everything/I’ve had but couldn’t keep”

Nick Cave & The Bad Seeds – ‘People Ain’t No Good’

Penned after breaking up with PJ Harvey, ‘People Ain’t No Good’ brings Cave’s poetic power to the fore in bleak, gut-wrenching form. 

Killer lyric: “To our love, send a dozen white lilies/To our love, send a coffin of wood/To our love, let all the pink-eyed pigeons coo/That people, they just ain’t no good”

Phoebe Bridgers – ‘Motion Sickness’

Bridgers describes lurching between being in love with someone and trying to free herself from their toxicity.  

Killer lyric: “I have emotional motion sickness/Somebody roll the windows down/There are no words in the English language/I could scream to drown you out”

Prince – ‘It’s Gonna Be Lonely’

‘It’s Gonna Be Lonely’ seems to be a hypothetical (and deeply sad) musing on what would happen if Prince and his lover ever split. What a pessimist!

Killer lyric: “Don’t you know it’s gonna be lonely/Without you love me/I know it’s gonna be lonely/Without you giving me every little single thing that I need”

Kacey Musgraves – ‘Space Cowboy’

Not all break-ups are heart-wrenching because their creators want to stay together – sometimes realising it’s time to part is just as crushing. 

Killer lyric: “After the gold rush, there ain’t no reason to stay/Shoulda learned from the movies that good guys don’t run away”

Sufjan Stevens – ‘Visions Of Gideon’

Taken from the Call Me By Your Name soundtrack, Stevens’ sorrowfully accepts it’s time to walk away and try to move on. 

Killer lyric: “I have loved you for the last time/Visions of Gideon, visions of Gideon/And I have kissed you for the last time/Visions of Gideon, visions of Gideon”

Lauryn Hill – ‘I Used To Love Him’

“He was the ocean and I was the sand,” Hill says of her ex, but things have since gone sour and they don’t complement each other anymore. 

Killer lyric: “I chose the road of passion and pain/Sacrificed too much and waited in vain/Gave up power, ceased being queen/Addicted to love like the drug of a fiend”

Solange – ‘Losing You’

Ignore the looped caws and claps at the start of this track and it’s utterly heart-rending, detailing a relationship cast over with doubt and dulled feelings. 

Killer lyric: “Tell me the truth boy, am I losing you for good?/We used to kiss all night but now there’s just no use”

Brandon Flowers – ‘Between Me And You’

Taken from Flowers’ second solo album, this remains one of his most shattering songs as he compares his old visions for the future for the turmoil he feels now. 

Killer lyric: “The heart don’t lie and that’s a good luck charm/But I’m watching it tear out of my arms/And there’s a power in letting go/I guess I didn’t want to let you know”

Angel Olsen – ‘May As Well’

Set to the gentlest guitar strums, Olsen sounds like an otherworldly torch singer as she reflects on a love gone awry. 

Killer lyric: “If you really love me, there’s no way to tell/I’m always arriving when you say farewell/In all of my dreams we are husband and wife/I’ll never forget you all of my life”

Lana Del Rey – ‘Ride’

The relationship portrayed in ‘Ride’ might not be The One, but there’s a fear and desperation to Lana’s pleas to not be left on her own again. 

Killer lyric: “Don’t leave me now/Don’t say goodbye/Don’t turn around/Leave me high and dry”

Elastica – ‘Never Here’

‘Never Here’ offers Justine Frischmann’s side to the demise of her relationship with Damon Albarn, blaming it on a couple out of sync and on the road. 

Killer lyric: “Then I started to worry/Thought of our lives left on the shelf/Too much TV and curry/Too much time spent on ourselves”


Daughter – ‘Smother’

Break-ups mean plenty of time to conduct post-mortems on your partnerships and ‘Smother’ sees Daughter’s Elena Tonra come to the conclusion she stifled hers. 

Killer lyric: “In the darkness I will meet my creators/And they will all agree that I’m a suffocator”

The Beach Boys – ‘Caroline, No’

Affairs are devastating, even if you decide to stick it out and give it a go. The Beach Boys’ paean to that experience heartbreakingly captures the difficulties of making it work post-infidelity.  

Killer lyric: “Could I ever find in you again/The things that made me love you so much then?”

Carole King – ‘It’s Too Late’

Carole King surveys her failed relationship with a sigh, wondering if it died because they changed or just stopped trying. 

Killer lyric: “But it’s too late, baby now it’s too late/Though we really did try to make it/Something inside has died and I can’t hide/And I just can’t fake it”

Roxette – ‘It Must Have Been Love’

The go-to break-up song if you want to feel like your heartbreak is part of the plotline in a classic rom-com. 

Killer lyric: “Make believing we’re together/That I’m sheltered by your heart/But in and outside, I turn to water/Like a teardrop in your palm”

Childish Gambino – ‘Sober’

Everyone has their own way of coping with a break-up. Donald Glover skips the pint of ice cream and soppy movie in favour of drowning his sorrows on this 2014 track. 

Killer lyric: “And now that it’s over, I’ll never be sober”

Harry Styles – ‘Falling’

Taking responsibility for your actions can be hard and, in this case, Styles is really regretting the consequences of his “wandering hands”. 

Killer lyric: “What am I now? What am I now? What if I’m someone I don’t want around?”

Jessie Reyez – ‘Coffin’

Toxic relationships might be bad for you, but sometimes you just can’t help overlooking the cons in favour of the intense love you feel.  

Killer lyric: “I had to watch ya jump from the roof/Boy I love you to death, just like a fool/We’ll need a coffin, handmade for two/Cos I love you to death, just like a fool”

Lucy Dacus – ‘Night Shift’

Sometimes, the last thing you want is to run into your old lover and Lucy Dacus offers a cheating ex a plan to never cross paths again. 

Killer lyric: “You don’t deserve what you don’t respect/Don’t deserve what you say you love and then neglect”

Arcade Fire – ‘Cars And Telephones’

Then there’s the times when you’d love to bump into an old flame but they’ve unhelpfully put a whole ocean between you. The only solution for Win Butler? Torment yourself and wallow. 

Killer lyric: “But fuck it, I love you no less/I’m going to feel like shit”

Boygenius – ‘Stay Down’

Julien Baker uses video game references and metaphors to describe falling out of love with someone, while likening the experience to trying to end a fight (“I’ll stay down”). 

Killer lyric: “I’m in the back seat of my body/I’m just steering my life in a video game”

Laura Marling – ‘New Romantic’

Marling might sound matter-of-fact on her 2007 single but the plainness in her delivery is all the more brutal – the sound of a love gone ice cold. 

Killer lyric: “I know I said I love you but I’m thinking I was wrong/I’m the first to admit that I’m still pretty young/And I never meant to hurt you when I wrote you 10 love songs”

FKA twigs – ‘Cellophane’

It’s only natural to blame yourself in a break-up and Twigs does just that as she mournfully tries to pinpoint what went wrong. 

Killer lyric: “And didn’t I do it for you?/Why don’t I do it for you?/Why won’t you do it for me?/When all I do is for you”

Bright Eyes – ‘Land Locked Blues’

A duet with Emmylou Harris, this 2005 track finds Conor Oberst planning an escape route, taking precautions to avoid painful experiences in the aftermath. 

Killer lyric: “If you walk away, I’ll walk away/First tell me which road you will take/I don’t want to risk our paths crossing some day”

The Beatles – ‘The Long And Winding Road’

Even The Beatles have their ones who got away and Paul McCartney reflects on an old relationship on this classic. 

Killer lyric: “The wild and windy night that the rain washed away/Has left a pool of tears, crying for the day/Why leave me standing here?”

Amy Winehouse – ‘Love Is A Losing Game’

Poor Amy was full of regret on this ‘Black To Black’ classic, ruing the day she let herself fall in love at all. 

Killer lyric: “Love is a losing game/One I wish I never played/Oh what a mess we made/And now the final frame/Love is a losing game” 

The Cure – ‘Pictures Of You’

As time goes by, people change and, here, Robert Smith is trying to cling on to who his partner once was – not who they’ve become. 

Killer lyric: “Remembering you/Fallen into my arms/Crying for the death of your heart”

Roy Orbison – ‘Crying’

People’s hearts move at different speeds and Orbison finds himself several beats behind his ex, hopelessly in love as they move on.   

Killer lyric: “I love you even more than I did before/But darling what can I do?/For you don’t love me/And I’ll always be crying over you”

Prince – ‘Purple Rain’

Prince’s partnership finds a slightly more finite end than most other break-up songs, set at the end of the world.

Killer lyric: “I never meant to cause you any sorrow/I never meant to cause you any pain”

Lorde – ‘Writer In The Dark’

Written about her first major heartbreak, Lorde documents the breakdown of a relationship with vivid intensity. 

Killer lyric: “I am my mother’s child, I’ll love you til my breathing stops/I’ll love you til you call the cops on me”

Liz Phair – ‘Divorce Song’

Phair equates a loss of love to losing your life on this deceptively jangly ode to reneging on your wedding vows. 

Killer lyric: “And the license said you had to stick around until I was dead/But if you’re tired of looking at my face, I guess I already am”

Sleater-Kinney – ‘One More Hour’

Corin Tucker wrote this song about bandmate Carrie Brownstein, who she briefly dated. She later revealed there was no other girl, but it still stands up as a document to the trials of love. 

Killer lyric:  “Don’t say another word/About the other girl”

Joni Mitchell – ‘River’

Not even Christmas can heal Mitchell’s heart, as she deals with reviewing a break-up in the middle of holiday festivities. 

Killer lyric: “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”

Abba – ‘The Winner Takes It All’

Although Björn Ulvaeus claimed the song’s divorce story didn’t take inspiration from his split with bandmate Agnetha Fältskog, his ex-wife’s emotional delivery made his words powerfully realistic.  

Killer lyric: “But tell me does she kiss like I used to kiss you?/Does it feel the same when she calls your name?/Somewhere deep inside, you must know I miss you”

Ariana Grande – ‘My Everything’

As the cliché goes, you don’t know what you’ve got til it’s gone – a lesson Ariana learned the hard way on ‘My Everything’. 

Killer lyric: “He wasn’t my everything til we were nothing/And it’s taking me a lot to say/Now that he’s gone, my heart is missing something”

Patsy Cline – ‘I Fall To Pieces’

Staying friends with an ex is a process that takes time and country queen Cline is struggling to come to terms with that on this sadly swooning gem. 

Killer lyric: “You want me to act like we’ve never kissed/You want me to forget, pretend we’ve never met/And I’ve tried and I’ve tried but I haven’t yet/You walk by and I fall to pieces”

Coldplay – ‘The Scientist’

Would things turn out different if you could rewind time and do things again? On ‘The Scientist’, Chris Martin is willing to find out rather than let everything go. 

Killer lyric: “Nobody said it was easy/It’s such a shame for us to part/Nobody said it was easy/No one ever said it would be this hard/Oh, take me back to the start”

Stevie Wonder – ‘Tuesday Heartbreak’

A funky break-up song but a break-up song nonetheless, Wonder struts sadly through a cruel tale as old as time – being left for another lover. 

Killer lyric: “Tuesday heartbreak seem to be unfair/Cos you say that you found another man/Tuesday break heart, guess you just don’t care/Cos you found another man”

Fleetwood Mac – ‘Landslide’

Moving on from someone is hard to do when they’ve become such a prominent figure in your life, as Fleetwood Mac mournfully explain. 

Killer lyric: “Well I’ve been afraid of changing/Cos I built my life around you”

In need of further wallowing? Here’s a playlist of all of these devastating break-up songs.

Let us know which one really strikes a nerve in the comments below.

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