The 50 best breakup songs

Heaven knows you’re miserable now—so you may as well enjoy it with the best breakup songs ever made



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“I Want You Back” by The Jackson 5 (1969)

“I Want You Back” by the Jackson 5

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.—Brent DiCrescenzo

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“September Gurls” by Big Star (1974)

“September Gurls” by Big Star

In the encapsulation of fall-semester romance, Alex Chilton plays tough: “I loved you, well, never mind.” Never mind, he shrugs. Right. By the next line he’s confessing, “I’ve been crying all the time.” Ah, being a teenager. Listening to Big Star, it’s impossible to forget.—Brent DiCrescenzo

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“Dry Your Eyes” by The Streets (2004)

“Dry Your Eyes” by the Streets

Men’s emotions can sometimes be harder to read than a pureed copy of Proust. In 2004, however, the Streets’ 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.”—Oliver Keens

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“Don’t Speak” by No Doubt (1996)

“Don’t Speak” by No Doubt

“Don’t Speak” was released in 1996 as the third single from No Doubt’s third album, Tragic Kingdom. The song, 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.—Kristen Zwicker

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“Crying” by Roy Orbison (1961)

“Crying” by Roy Orbison

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.—Adam Feldman

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“Skinny Love” by Bon Iver (2008)

“Skinny Love” by Bon Iver

You don’t even need to be able to understand the words in this 2007 hipster breakup anthem to recognize that this is the sound of a man in pain. Justin Vernon’s post-breakup isolation in a rural Wisconsin cabin for one lonely winter is now the stuff of indie-folk legend. But for a singer-songwriter who became known for his ethereal falsetto, it’s surprising how truly angry he sounds here. The lyrics are obtuse, but the clearer ones (“I tell my love to wreck it all / Cut out all the ropes and let me fall”) paint a vivid emotional picture.—Jenna Scherer

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“No Distance Left to Run” by Blur (1999)

“No Distance Left to Run” by Blur

From the bleak opening line—“It’s over, you don’t need to tell me”—to Damon Albarn’s final cries, this song is like a punch to the gut. Written, allegedly, about Albarn’s split with Elastica frontwoman Justine Frischmann, the tune perfectly encapsulates the weariness and resignation all too often experienced during a breakup, in that period between acceptance and finally moving on. Sigh.—Amy Plitt

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“Teardrops” by Womack & Womack (1988)

“Teardrops” by Womack & Womack

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.—Jonny Ensall

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“Believe” by Cher (1998)

“Believe” by Cher

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.—James Manning

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“Say Hello, Wave Goodbye” by Soft Cell (1982)

“Say Hello, Wave Goodbye” by Soft Cell

“Take your hands off me!” cries Marc Almond on this 1982 synth-pop tearjerker. “I don’t belong to you, you see.” The follow-up to Soft Cell’s hit single “Tainted Love,” “Say Hello” perfectly encapsulates the ambivalence and denial at love’s end. Almond reflects that the pair must’ve been “the standing joke of the year,” adding later, “I never knew you / You never knew me.” And of course, were any of this true, you wouldn’t be crying now, would you?—Sophie Harris

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Users say

Rufus B
Rufus B

Bruce Springsteen's "Stolen Car" - devastating. It's over right after it starts... "We got married and promised never to part, then little by little we broke each other's heart..."

I Would add the following...Poke-Frightened Rabbit   Amsterdam-Guster  Burning Photographs-Ryan Adams and How You Like Me Now?-The Haavy