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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30
“I Keep Forgettin’ (Every Time You’re Near)” by Michael McDonald (1982)

“I Keep Forgettin’ (Every Time You’re Near)” by Michael McDonald

We don’t typically think of the breakup song as a climate hospitable to sultry funk, but somebody forgot to notify Michael McDonald. On this 1982 lite-rock staple, the former Doobie Bro laments being hung up on an ex, as a rhythm section stocked with session aces glides through a monster groove—famously sampled by Warren G on 1994’s “Regulate.” Whoever the subject of the tune was, it’s hard to imagine her not shimmying back into the husky crooner’s arms when she heard this immortal jam.—Hank Shteamer

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29
“Blame Game” by Kanye West featuring John Legend (2010)

“Blame Game” by Kanye West featuring John Legend

Mark this down: November 2010. The last time Kanye demonstrated vulnerability on a record. With an Aphex Twin sample, West balanced anger, pain and smartassery like no other MC can. It’s touching. That is, if you plug your ears before Chris Rock comes in for the coda, exclaiming, “This is some Cirque du Soleil pussy now!” By the next album, Yeezus would be a married man, grudge-rapping about fisting and ejaculating on fine fur coats.—Brent DiCrescenzo

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28
“Irreplaceable” by Beyoncé (2006)

“Irreplaceable” by Beyoncé

The Destiny’s Child songbook is a bible for the woman looking to keep her man on his toes. Just in case “Bills, Bills, Bills,” “Say My Name” and “Survivor” didn’t send a clear enough message, Beyoncé reiterated her “Don’t get too comfortable” party line on this, the ultimate kick-you-to-the-curb anthem. The singer doesn’t sound the slightest bit perturbed as she shoos a disappointing lover out of her crib, advising him that he’ll find his worldly possessions “in a box to the left.” You’re tempted to shout out an “Amen,” but Queen Bey seems to be doing just fine without any reinforcement.—Hank Shteamer

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27
“Ex-Factor” by Lauryn Hill (1998)

“Ex-Factor” by Lauryn Hill

“Doo Wop (That Thing)” may have been the flagship single from Lauryn Hill’s post-Fugees solo debut—1998’s multi-Grammy-winning The Miseducation of Lauryn Hill—but it was the languid, lovely “Ex-Factor” that rocketed the disc into the realms of extraordinary. Perfectly piquant down to the name of the song, “Ex-Factor” longs for things to be different while knowing they can’t be, ringing with frustration (“I keep letting you back in”) but humming with a love that refuses to fade.—Sophie Harris

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26
“The Tracks of My Tears” by Smokey Robinson and the Miracles (1965)

“The Tracks of My Tears” by Smokey Robinson and the Miracles

Ah, the tears of a clown. Smokey might, indeed, “be the life of the party,” but “deep inside [he’s] blue,” people. As with the best soulful weepers, “Tracks” beautifully and economically articulates the pain of missing the one that got away. This summer-of-’65 staple—a cocktail of Smokey’s golden voice, swirling strings and horns, and a sing-along-worthy chorus—rings just as true today.—Tim Lowery

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25
“Pain In My Heart” by Otis Redding (1964)

“Pain In My Heart” by Otis Redding

Over and again, whether hopeful or heartbreaking, Otis Redding’s exquisite love songs bring us to our knees, like this title track off the soul icon’s 1964 debut album for Stax Records subdivision Volt (which also includes the imploring “These Arms of Mine”). If you’re really in the mood to wallow, mourn the fact that Redding perished in a plane crash at age 26, just three days after recording “Dock of the Bay.”—Kate Wertheimer

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24
“It’s Too Late” by Carole King (1971)

“It’s Too Late” by Carole King

Carole King’s era-shaping 1971 album, Tapestry, was in some sense a declaration of independence from Gerry Goffin, her former husband and songwriting collaborator. The album’s first single, “It’s Too Late,” treats the end of a once-cherished relationship with bittersweet maturity, strength and striking lack of recrimination: “Still I’m glad for what we had / And how I once loved you.” It’s a song about being realistic about the end—a sentiment made all the more moving by its initial pairing, as a single, with the tremblingly erotic “I Feel the Earth Move.”—Adam Feldman

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23
“Heartbreak Hotel” by Elvis Presley (1956)

“Heartbreak Hotel” by Elvis Presley

Think your breakup is sad? This song’s lyrics were inspired by a 1956 newspaper article about a man who jumped to his death from a hotel window, leaving a note with the single line “I walk a lonely street.” But suicides don’t sell records, so Presley crooned instead about a place where the bellhop’s tears flow, the desk clerk dresses in black and brokenhearted lovers can cry away their gloom. (And potentially hook up? Was this place also a brothel? No? Opportunity lost.)—Kate Wertheimer

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22
“I Fall to Pieces” by Patsy Cline (1961)

“I Fall to Pieces” by Patsy Cline

We’ve all been there: certain that you’re finally, finally over your ex, and then you run into them on the sidewalk, or hell, someone even mentions their favorite kind of muffin in passing, and you’re Jell-O on the floor. Patsy knows, child. And Patsy understands. Curl up in this 1961 tune's velvety vocals and keening pedal steel, and just let it all out.—Jenna Scherer

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21
“Come Pick Me Up” by Ryan Adams (2000)

“Come Pick Me Up” by Ryan Adams

A complimentary shot (or five) of whiskey ought to be issued with every copy of Ryan Adams’s 2000 disc, Heartbreaker (his debut album after leaving Whiskeytown, as it goes), such is its drink-away-the-despair musical might. “Come Pick Me Up” is gloriously masochistic, its chorus a veritable lunge of awful longing and too many cigarettes—“Take me out / Fuck me up / Steal my records / Screw all my friends.… / And then do it again / I wish you would”—followed by a killer harmonica caterwaul. Does it help to know that the album was named after the Mariah Carey song?—Sophie Harris

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Users say

5 comments
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

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