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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10

“I Will Always Love You” by Whitney Houston

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.—Adam Feldman

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9

“You’ve Lost That Lovin’ Feelin’” by the Righteous Brothers

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.—Adam Feldman

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8

“Someone Like You” by Adele

You’d have to be some kind of monster not to mist up a bit at Adele’s 2011 tear tugger. A Saturday Night Live sketch has been written about its irresistible emotional pull; even dogs, it seems, are not immune. Part of what gives the song this power, paradoxically, is its rejection of sadness. The heartbroken singer enacts a performance of brave stoicism (she’s fine, she’ll move on, she’ll find someone else), but we know that she is fooling herself (she’s a mess, she’s still stuck, the best someone else is still the guy she has lost). But her willful refusal to cry about it lets us do the sobbing for her.—Adam Feldman

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7

“Go Your Own Way” by Fleetwood Mac

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.—Oliver Keens

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6

“Tangled Up in Blue” by Bob Dylan

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.—Sophie Harris

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5

“Hey, That's No Way to Say Goodbye” by Leonard Cohen

Tear-jerking Canadian 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.—Jonny Ensall

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4

“What Becomes of the Brokenhearted” by Jimmy Ruffin

What becomes of the brokenhearted? They end up listening to this solid-gold soul classic, over and over again, is what. The sad and newly-single can find solace in its driving, determined verses; tantalizing string refrain; major-to-minor key changes; and knowledge that yes, we’ve all been through it, and survived. Recorded in 1966 for Motown, the song is among the label’s most-covered hits. Anyone who’s turned to music for comfort (that’ll be all of us, then) will understand why.—Sophie Harris

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3

“Nothing Compares 2 U” by Sinead O’Connor

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 the Parc de Saint-Cloud (a historic park just outside of Paris), was cited by Miley Cyrus as the inspiration for her 2013 “Wrecking Ball” video. Whatever your opinion of that spectacle, it can’t be denied that more than two decades later, O’Connor’s wrenching rendition still packs a punch.—Kristen Zwicker

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2

“You Oughta Know” by Alanis Morissette

Purported subject of this song Dave “Uncle Joey” Coulier insists that his breakup with Alanis was amicable. But there’s nothing well-wishing about this most vengeful of jilted-lover odes, the object of many a cathartic karaoke jam since its release in 1995. Like all great rages, Alanis lets hers build: The tune begins like an unexploded bomb, and you can almost smell the cordite in the air as she murmurs: “I want you to know / I’m happy for you…” And then the guitar kicks in, and the uncomfortable questions begin: “Is she perverted like me? / Would she go down on you in a theater?” By the time she’s growling about scratching her nails down someone else’s back and hoping you feel it, it’s already too late, Coulier. This one’s for the most demonstrative of your five stages—white-hot anger.—Jenna Scherer

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Users say

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

Listen to Time Out's 50 best breakup songs playlist on Spotify

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