The 50 Greatest Breakup Songs of All Time

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The 50 Best Breakup Songs of All Time

The best heartache a half-century of music can provide.

We recently assembled the greatest love songs of all time, but let's face it: while love has inspired some great songs, the majority of classics come from a darker place. Our rules this time were simple: one, a breakup song can be vengeful, dignified, devastated, or whatever else, as long as the lyrics make explicit reference to a relationship that is ending or has ended. Two, we limited it to one song per principal songwriter. Three, this list goes back to 1960, which we feel represents the dawn of pop music as we know it, but we apologize to Edith Piaf, Frank Sinatra, Mozart, et al. Okay, now you can tell us what we missed. Have fun, and be sure to check out this Spotify playlist of our picks. — The Hooksexup Editors


50. Kelly Clarkson, "Since U Been Gone" (2004)

Obnoxious text-speak aside, this is how you build a pop song. Clarkson's voice starts out low, the drums sound like a Casio keyboard, and you're wondering what's so great about this club and why you've been dragged here when you just want to sulk at home. Then that chorus decks you in the face, and before you know it, you've had four shots because you're so fucking fierce and you don't need him (or her), you don't need anyone and you're jumping around like an idiot… and here comes that chorus again! — A.H.


49. Human League, "Don't You Want Me?" (1981)

Unlike almost every other breakup song ever written, "Don't You Want Me?" gives us both sides of the story, featuring the lead singer, Philip Oakey, dueting with bandmate Susan Ann Sulley. Together, they give us arguments from the spurned and the spurner. But victory goes to the shout-along chorus, which surely anyone can relate to. — J.G.


48. The Buzzcocks, "Ever Fallen In Love… (With Someone You Shouldn't've)" (1978)

Of the great early punk bands, only The Buzzcocks were predominately concerned with love. "Ever Fallen In Love" has a weary fatalism that belies the fact that it was written by a twenty-three-year-old. Having fallen in love with the wrong person, the singer finds himself completely at her mercy; he doesn't seem to get a vote in things. — P.S.


47. Dolly Parton, "I Will Always Love You" (1974)

Forget everything you ever knew about Whitney Houston's version of this song. You can hear the heartbreak in Dolly Parton's voice as she gracefully ducks out of a tumultuous relationship. There's something comforting about the dignity the song finds in ending a relationship peacefully, even if things are usually a lot messier in real life. — J.G.


46. Wilco, "I Am Trying to Break Your Heart" (2002)

Jeff Tweedy often seems to be trying to obscure his emotional songwriting with avant-garde touches like weird ambient sounds, deliberately "wrong-sounding" notes, and obtuse lyrics. But none of those elements can stop "I Am Trying to Break Your Heart" from succeeding in its titular aims. — A.H.


45. The Cure, "Pictures of You" (1989)

"Pictures of You" is so devastating because it perfectly nails the mixed feelings of reminiscing about a past relationship — how we return to certain memories time and time again until they take on life of their own. "I've been Facebooking for so long at these pictures of you" doesn't have quite the same feel, but the sentiment is still the same. — A.H.


44. Dire Straits, "Romeo and Juliet" (1980)

Unlike whatshisface's play, this "Romeo and Juliet" suggests that love can end in tragedy without anyone getting poisoned. The implied contrast to a legendary romance makes Mark Knopfler's breakup sound all the sadder. — S.M.


43. The Temptations, "I Wish It Would Rain"

While "I Wish It Would Rain" is about a man hoping for inclement weather to hide his tears because "a man ain't supposed to cry," I suggest ignoring that somewhat dated sentiment and thinking about those gloriously self-absorbed days we all have after a breakup, when we wish the rest of the world would feel as dismal as we do. Then put this song on and let David Ruffin sweep you into a world of heartbreak. — A.H.


42. Weezer, "Butterfly" (1996)

Closing out a near-perfect album of guilt and angst, "Butterfly" is a devastating story about the guilt of being unable to commit. Totally exposed, Rivers Cuomo confesses to having hurt someone who didn't deserve it. He tries to figure out why he did it, but in the end, all he has are two plaintive words: "I'm sorry." — P.S.


41. Elvis Costello, "I Want You" (1986)

This must be the most intense song that Elvis Costello ever recorded. It's like he's trying to scare the girl into coming back to him under the penalty of some kind of love-knifing. Spitting out lines like "I might as well be useless for all it means to you," he captures the bitterness of a breakup perfectly. — J.G.


40. Soft Cell, "Tainted Love" (1981)

Originally performed by Gloria Jones in the '60s, "Tainted Love" got a new life from Soft Cell's danceable, synth-heavy remake. Fittingly for a tune about trying to get out from under someone's spell, it's almost impossible not to sing along. — R.K.


39. New Order, "Age of Consent" (1983)

In an angsty moment, count on a great keyboard riff to make you feel like it's going to be okay. See "Age of Consent." At once calming, classy, and catchy, this is a requiem for a mostly-adult relationship. Maybe the Brits are just more composed than us, but, while cutting, "Age of Consent" also sounds almost polite. — Rachel Krantz


38. No Doubt, "Don't Speak" (1996)

Originally a celebration of love between Gwen Stefani and Tony Kanal, "Don't Speak" was later rewritten to reflect their breakup. Through Stefani's remorse-laden voice, it reminds of us the times we want to shrink away from the harsh truth, and choose silence over angry words. — J.G.


37. Jeff Buckley, "Lover, You Should've Come Over" (1994)

Jeff Buckley's more known for his epochal cover of "Hallelujah," but "Lover, You Should've Come Over" showcases the sophistication of his own songwriting. With chords more inspired by jazz than rock and a voice that sounds decades wearier than it has any right to, "Lover" is an elegiac ode to lost love from someone who seemed to know more about losing love than any of us. — A.H.


36. Notorious B.I.G., "Friend of Mine" (1994)

This is an ode to those relationships in which both parties screw everything up royally. Biggie gives us the backstory of himself and his lady, which is rife with lies, infidelity, and smack-talkin'. Sometimes the only direction you can point your finger is at yourself. — J.G.


35. Liz Phair, "Fuck and Run" (1993)

The musical, lyrical, and spiritual opposite of "November Rain," "Fuck and Run" is wistful and blunt. A not-very-passionate relationship is dropping off, and it sounds like it's only the most recent of many. This is the lament of someone who wants something more, but is too paralyzed to reach for it. — P.S.


34. Bon Iver, "Skinny Love"

If you're trying to make haunting breakup music, heading into exile in the woods of Wisconsin is almost cheating. But the results speak for themselves. This is heartache on a different level; sadness for the one who left and remorse for the person you've become. — J.G.


33. The Walkmen, "The Rat" (2004)

To really understand this song, you need to watch a live version and see how furiously guitarist Paul Maroon strums the intro. Then Matt Barrick starts beating his drums like they killed his dad, and one of the most righteously pissed-off breakup songs of the decade is off to the races. It's a gloriously spiteful kiss-off, and one perfect for pounding the pavement after a breakup. — A.H.


32. Roy Orbison, "In Dreams"

Roy Orbison's best songs are operatic, in the best sense of that word. Not just because of his preternaturally athletic voice, but because of their narrative momentum. "In Dreams" is a perfect example: in contrast to the rigid structure of most pop music, the song moves forward, unfolding new sections rather than returning to old ones. When Orbison hits that spine-tingling high note at 2:28, it's like every third-reel climax rolled into one beautiful moment. — A.H.


31. Led Zeppelin, "Tangerine" (1970)

"Tangerine" should probably appear in the dictionary next to the word "wistful." With its sweet vocal harmonies and beautiful slide guitar, it's a perfect picture of a past relationship that hasn't quite lost its ache in the recollection. — P.S.


30. The Jesus and Mary Chain, "Just Like Honey" (1985)

With brutal honesty, "Just Like Honey" describes what runs through your brain when you find yourself back with the person who can only be described as a total life ruiner: "I'll be your plastic toy." It'll give you that desperate moment of clarity you need if you find yourself making all the wrong choices. — J.G.


29. Justin Timberlake, "Cry Me A River" (2002)

Who ever would've thought that the dopey, fresh-faced bleach-blonde from 'NSYNC would grow up to have this much soul? If JT wants me to cry, damn it, I'm cryin'. — J.G.


28. The Magnetic Fields, "All My Little Words" (1999)

Writing a song is always an act of hope — you'll get your feelings across to someone in a way that matters. You'll create or reaffirm a connection. But after a breakup, all hope is lost, and not even a craftsman as crafty as Stephin Merritt can write anything to fix it. Meaning itself is annihilated, leaving just a pile of forlorn verbiage. I wish I could write songs this good, but then, what difference would it make? — P.S.


27. The Replacements, "Answering Machine" (1984)

The Replacements were notorious for sandwiching heartbreakers like this between ludicrous pisstakes. On Let It Be (even that title!), "Answering Machine" follows closely on the heels of something called "Gary's Got A Boner." No matter; the band's flippant side actually throws the vulnerability of songs like "Answering Machine" into sharper relief. Over an intricate guitar figure, Paul Westerberg yearns to reconnect to a distant girlfriend, but it's clear she's slipping away. — P.S.


26. The Beach Boys, "Caroline, No"

This musically baroque piece laments a girl who's gone or changed in many ways, an idea not that different from dozens of other songs The Beach Boys had recorded by 1966. But the wandering melody, harpsichord vamp, and rattling sound effects are way, way creepier than "Help Me, Rhonda" ever dreamed of. In its sense of devastating loss, "Caroline, No" almost sounds like it's sung from beyond the grave. — P.S.


25. Billy Bragg, "Must I Paint You a Picture" (1988)

"A New England" is a great song, but "Must I Paint You a Picture" is one of the most moving, accurately sketched portraits of a relationship killed by overthinking: "The temptation to take the precious things we have apart to see how they work must be resisted, for they never fit together again." Ouch. — A.H.


24. Paul Simon, "Hearts and Bones" (1983)

Conventional wisdom probably gives the nod to "Graceland" (a great one, no doubt), but we've got to go with "Hearts and Bones," an ambivalent masterpiece about Simon's troubled marriage to Carrie Fisher. These two very different people "return to their natural coasts," but a complex, difficult connection remains: "You take two bodies and you twirl them into one — their hearts and their bones — and they won't come undone." Both tender and sharp, "Hearts and Bones" might be the greatest lyric Simon's ever written. — P.S.


23. Macy Gray, "I Try" (2000)

Though she was unable to capitalize on it, Macy Gray will always be remembered for this perfect pop gem. Her odd vocal affectations (exactly what accent is that, again?) bump up against her band's joyously swinging performance, and by the end of the song, you're less aware of her voice's gravelly timbre than with its exuberance — she's made heartbreak sound like a party. — A.H.


22. Nina Simone, "Ne Me Quitte Pas"

"Ne Me Quitte Pas" may not be Nina Simone's most well-known performance, but it's definitely one of her best. You don't need to speak French to hear that this song is about begging someone not to leave. A work of exhausted beauty, it's best listened to on repeat accompanied by a bottle of red and a good cry. — R.K.


21. The Strokes, "Someday" (2001)

Equal parts regret and boozy barstool philosophy, "Someday" is a broadly focused portrait of a breakup. Though the line "alone we stand, together we fall apart" hints at a relationship dissolved for its own good, the song is as much about letting go of youth as it is about letting go of someone, and Julian Casablancas' disaffected croon obscures some of his most painfully sincere lyrics. — A.H.


20. Rolling Stones, "Angie" (1973)

While most breakup songs come from a place of anger or devastation, in "Angie," Jagger/Richards insist on ending the relationship on a joyful note: "Ain't it good to be alive?" As Mick croons the story of his relationship's painful past, it only serves to emphasize how much better things are going to be now that the relationship is over. It's a breakup song for grownups. Natasha Ochshorn


19. Sam Cooke "Bring It On Home To Me"

Lou Rawls' uncredited backing vocals on this song lend it a commiserating, drinking-buddies-on-a-breakup-bender feel. Cooke and Rawls' voices dip, swell, and surge together, and for all the sadness here, there's a comforting blanket of friendship over the whole song. It's one man with his arm around his friend at the back of the bar, letting him know that he's better off, even if they both know he doesn't really mean it. — A.H.


18. Joni Mitchell, "A Case Of You" (1971)

You really can't talk about breakup songs without talking about Joni. There are lots of strong contenders on Blue, but "A Case Of You" is the one track we don't want to get over. This song could be about a lot of situations — an already broken relationship, a relationship in the process of breaking, or the anticipation of doomed love. So "A Case Of You" will be what you need it to be. — R.K.


17. Elliott Smith, "Oh Well, Okay" (1998)

In a discography full of gorgeous, devastating breakup songs, it's hard to pick just one. (Also nominated: "Say Yes," "Waltz #2," "Miss Misery," "Between the Bars," "The Biggest Lie," "Condor Ave.," etc.) But "Oh Well, Okay" might be the best of the bunch, a sigh of resignation wedded to one of the most beautiful melodies poor Elliott Smith ever wrote. — P.S.


16. Marvin Gaye, "I Heard It Through the Grapevine" (1968)

It was Motown producer Norman Whitfield's idea to have Marvin Gaye sing this song in a register close to the top of his range, so the desperation in his voice is equal parts physical and emotional. But the rest of the song's genius is in the arrangement: sinister electric piano, and pounding tribal drums, a perfect sonic approximation of infidelity-related paranoia. — A.H.


15. Joy Division, "Love Will Tear Us Apart" (1980)

This must be the most sepulchral song ever to have become a massively influential international hit. Maybe it's only in retrospect, but it's almost impossible to hear "Love Will Tear Us Apart" without thinking that someone's about to kill himself. — P.S.


14. Willie Nelson, "Always On My Mind" (1982)

The apology song is a difficult one to pull off — if the song is too self-flagellating, it becomes more about the singer than the person they've wronged. But Willie Nelson gives "Always On My Mind" a perfect balance of regret and resolve. His sandpapery rasp and restrained delivery are the real reason this song — covered by so many others — belongs to him. — A.H.


13. Rod Stewart, "Maggie May" (1971)

The deceptively nuanced lyrics, Stewart's wistful vocal, and the band's rustic, ramshackle feel make "Maggie May" one of the most heartfelt portraits of a disintegrating relationship ever recorded. That it's a May-December relationship doesn't make any difference — this relationship wasn't a novelty to the people in it, and it shouldn't be to the listener, either.— A.H.


12. Fleetwood Mac, "Landslide" (1975)

Unlike most breakup songs, "Landslide" speaks from the moment right before things actually fall apart. Stevie Nicks wrote it while stranded on a mountain in Colorado, contemplating the coming end of her relationship with Lindsay Buckingham; it's melancholic and uncertain, but like many of Nicks' songs, it also has an appealing toughness. Time makes you bolder, after all. I thought this song was sad and pretty when I was half the age I am now; today, I see more in it than that. — P.S.


11. Sinead O'Connor, "Nothing Compares 2 U" (1990)

In my opinion, this is one of the few covers that blows the original out of the water. (My apologies to all the Prince fans out there.) With devastating honesty, Sinead O'Connor mourns a straying lover, while celebrating the freedom of being alone again. Life's great buffet is hers for the taking, but it's all lost its taste. — J.G.


10. Jackson 5, "I Want You Back"

Written about a relationship that ended prematurely, and a lover hastily backpedaling to save it, "I Want You Back" evokes all the mistakes of young lovers in the heat of passion. Regardless of the upbeat tone (and the fact that it was sung by an unusually soulful eleven-year old), this song is a glum reminder that once a relationship is over, something will be lost forever and ever. — J.G.


9. The Smiths, "I Know It's Over" (1986)

"I Know It's Over" finds the normally self-obsessed Morrissey stunned into a place of universal compassion. A breakup has rendered him vulnerable to the point of fetal ("The sea wants to take me/ The knife wants to slit me"), but he finds a way to a profound insight: "It's so easy to laugh, it's so easy to hate/ It takes strength to be gentle and kind." Over nearly six minutes, he touches on nearly every aspect of breakup psychology. The song is vast, chilling, and completely devoid of The Smiths' usual winking. — P.S.


8. Bill Withers, "Ain't No Sunshine (When She's Gone)" (1971)

"Ain't No Sunshine" is in an unusual key — "pure minor," which is rare in pop music. Maybe it's that, or Withers' devotional repetition of "I know" in the third verse, but the song comes across less as vintage '70s R&B and more as something older; something sacred, even. — A.H.


7. Etta James, "I'd Rather Go Blind"

Over a hypnotic, two-chord vamp, Etta James bares her soul to the point of bloodletting. Her performance starts off relatively low-key and mournful, but by 1:30 ("I was just, I was just, I was just sitting here thinking of your kiss, and your warm embrace"), she's fully in the over-the-top truth of the song: sometimes, it'd be easier to never see again than see someone you love walk away. — A.H.


6. Smokey Robinson & The Miracles, "The Tracks of My Tears"

Smokey Robinson's gossamer vocals are downright angelic on this song: his voice is so pure, and his pain so impossibly transparent, it's like looking through a beautiful window into a house destroyed by fire. The song's dynamic shifts have a lot to do with its success as well: as the restrained verse accelerates into that skyrocketing chorus, the strings swell, the drums crash, and Smokey's voice wavers above it all, sounding, well, like an angel. — A.H.


5. Harry Nilsson, "Without You" (1971)

When he first heard Harry Nilsson sing, Little Richard was supposed to have said, "My! You sing good for a white boy!" That is a dramatic understatement. "Without You" is such a commanding performance carried off with such tenderness that when Nilsson's voice cracks on that heroically high note at 2:09, you're a little unsure as to whether it was too tough on him physically or emotionally. Either way, wow. — A.H.


4. Prince, "When You Were Mine" (1980)

The perfect craft of "When You Were Mine" might conceal the hurt at its core. No one would blame you for getting distracted by the huge guitar, vocal, and keyboard hooks — or by the revolutionary-for-its-time gender ambiguity of the narrative. But under all that is a simple, biting observation about human nature: "I love you more than I did when you were mine." — P.S.


3. Outkast, "Ms. Jackson"

This is probably the only breakup song ever addressed to the singer's mother-in-law, but the gambit pays off. By directing his imploring lines to Erykah Badu's mom instead of Badu herself, Andre 3000 makes an implicit statement about how the idealism of young love ("that crib with the Goodyear swing") gives way to the complexities of adulthood: private schools, day care, lawyers. Mothers-in-law. It's rueful, but it's loving too. — P.S.


2. The Beatles, "For No One"

Among Paul McCartney breakup songs, conventional wisdom would give the edge to "Yesterday." But while "Yesterday" is certainly beautiful, with its sweeping strings and simple lyrics, it's more adolescent in its mood than the brutally adult "For No One." Here, McCartney strips out all sentiment in favor of a crisp, hard-headed look at the end of a relationship. It's devastating (and very English). "Yesterday" feels speculative, and McCartney wrote it when he and Jane Asher were still happily together; "For No One," written while they were breaking up, could only have been written by someone who'd been there. — P.S.


1. Bob Dylan, "Don't Think Twice, It's All Right"

Dylan wrote this classic after his girlfriend, Suze Rotolo (who appears on the cover of The Freewheelin' Bob Dylan), told him she was extending her trip to Italy… indefinitely. In a perfect expression of rejection and bitterness, Dylan fills this song with slow burns like "I once loved a woman, a child I'm told/ I give her my heart but she wanted my soul," and of course, that final punch to the stomach, "You could have done better but I don't mind/ You just kinda wasted my precious time/ But don't think twice, it's all right." There's really no better song to listen to when you're hurt but don't want to hurt your pride. — R.K.


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