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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 Nerve 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.