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The 51 best breakup songs

Commiserate or celebrate being newly single with these breakup songs from classic tear-jerkers to epic kiss-offs

By Sophie Harris and Time Out editors |
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We figure you're charting your heartbroken way here a few months after scouring our best love songs playlist—sorry to hear the bad news. Sure, the best breakup songs might not be all celebration and joy, but we're here to remind you: It doesn't have to be all doom and gloom either! Turn to Cee-lo to keep your angry head held high alongside a raised middle finger, or bask in your own independence and self-love with Ariana Grande. And if neither of those reponses resonate with you, then worry not, because this playlist includes plenty of simple old-school wallowing too. So cue-up this playlist, peruse a few dating apps and then maybe crank the best party songs for a weekend bender to remind yourself: You're better off single!

Listen to the best breakup songs playlist

Best break up songs

11

“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

Most heartbreaking lyric: “We both know I’m not what you need.”

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12

“I Will Survive” by Gloria Gaynor

Is there any song that combines female empowerment and discofied schmaltz with the same efficacy as Gloria Gaynor’s “I Will Survive”? With lyrics like “I’ve got all my life to live / I’ve got all my love to give / And I’ll survive, I will survive”—not to mention a soaring melody accented by horns and strings galore—probably not. In fact, we think the Grammy-winning hit, released in late 1978, is one of the best “screw you, loser—I’m over you” tunes of all time.—Bruce Tantum

Most heartbreaking lyric: “I used to cry / but now I hold my head up high!”

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13
“Fuck You” by Cee Lo Green (2010)

“Fuck You” by Cee Lo Green

An old-school Motown-style soul number with a gleefully foul mouth, “Fuck You” was Cee Lo Green’s first solo single after he’d spent years crooning for Goodie Mob and Gnarls Barkley. It’s a shout-along, four-minute middle finger to a gold-digging ex (despite Green unconvincingly recasting it as a dig at the music industry), packing in punning verses, a wailing bridge and that glorious quadruple-fuck chorus. Even though the version everyone heard on the radio was heavily censored and retitled “Forget You,” it was one of the biggest songs of 2010. Needless to say, no one was singing the bowdlerized version. Forget that.—James Manning

Most heartbreaking lyric: “I guess he's an X-box, and I'm more Atari / But the way you play your game ain't fair”

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14
“Back to Black” by Amy Winehouse (2007)

“Back to Black” by Amy Winehouse

The late singer-songwriter crooned plenty about addiction, depression and heartbreak, but nowhere more brutally than in this moody torch song, which gave its title to her 2007 album. Winehouse penned this hit single about her falling back into bad habits after her very public break with husband Blake Fielder-Civil. The gloomy repetition of the word black during the bridge is the sound of a spiral into darkness—albeit a funky one.—Jenna Scherer

Most heartbreaking lyric: “Life is like a pipe / And I'm a tiny penny rolling up the walls inside”

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15
“I Just Don’t Know What to Do With Myself” by The White Stripes (2003)

“I Just Don’t Know What to Do With Myself” by the White Stripes

Though this song was originally sung by Tommy Hunt in 1962 (and has since been covered by myriad musicians, including Dusty Springfield, Dionne Warwick, Isaac Hayes and Elvis Costello), no one has been able to capture the desperation—and frustration—behind the lyrics quite like Jack White III. Recorded for the 2003 White Stripes release Elephant, this rock & roll version is perfect for the transition from heartbroken to pissed off. Bonus: Sofia Coppola directed a lingerie-clad, pole dancing Kate Moss in the music video, which should at least help get your blood pumping again.—Kate Wertheimer

Most heartbreaking lyric: “Like a summer rose needs the sun and rain / I need your sweet love to beat love away”

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16
“I Heard It Through the Grapevine” by Marvin Gaye (1968)

“I Heard It Through the Grapevine” by Marvin Gaye

You know even before the drumbeat kicks in that something is gonna go down in this song. And for anyone who’s had to hear the cheatin’, lyin’ news from someone else, this 1968 Motown single hits home. It’s become an acclaimed, Grammy Hall of Fame soul classic, covered by a range of musicians including Creedence Clearwater Revival (which made an 11-minute version for its 1970 album, Cosmo’s Factory) and claymation group the California Raisins (grapevine, raisins, see what they did there?).—Kate Wertheimer

Most heartbreaking lyric: “I know a man ain't supposed to cry / But these tears I can't hold inside”

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17
“How Can You Mend a Broken Heart?” by Al Green (1972)

“How Can You Mend a Broken Heart” by Al Green

Look, just because you’ve had your heart broken, it doesn’t mean that your mojo has to wilt away and die too—and the Reverend Al is here to spell that out via his definitive 1972 version of the Bee Gees cut. He aches just like you, but his hope hasn’t died (“Please help me mend my broken heart / And let me live again”)—and Al’s signature slow, sensual soul arrangements prove that it’s not just his heart that’s stirring.—Kate Wertheimer

Most heartbreaking lyric: “How can a loser ever win?”

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18
“Warning Sign” by Coldplay (2002)

“The Scientist” by Coldplay

So potent are the breakup songs on Coldplay’s second album, 2002’s A Rush of Blood to the Head, that it may as well come with an advisory sticker for the recently split up: These songs will make you wallow in heartbreak like it’s a warm, sad bubble bath. Which may be exactly what you need. “Nobody said it was easy,” croons Chris Martin. “No one ever said it would be so hard.” And then, after the song’s sucker-punch pause: “Oh, take me back to the start.”—Sophie Harris

Most heartbreaking lyric: “Science and progress do not speak as loud as my heart”

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19

“I Don't Want to Get Over You” by the Magnetic Fields

The premise behind Stephen Merritt's magnum opus concept album 69 Love Songs is pretty explicit (hint: it's 69 love songs), but a twist hides within: he's stated the love songs are really about love songs. The obtuse statement makes sense alongside the meta-awareness this song demonstrates in quips like "I could dress in black and read Camus / Smoke clove cigarettes and drink vermouth"—it's not just a breakup narrative, but an exposé on what types of narratives we write ourselves into. So hopefully that heady conceptual business will keep your mind occupied while you try to forget about that ex.

Most heartbreaking lyric: “I guess I should take Prozac, right? / And smile all night at somebody new”

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20
“Against All Odds (Take a Look At Me Now)” by Phil Collins (1984)

“Against All Odds (Take a Look At Me Now)” by Phil Collins

When you’re dumped, you’re allowed to indulge in melodrama. It is acceptable to sit around in a robe for days and take big bites of the pillow synthesizers, ice-cream crooning and cookie-dough drums comprising this most powerful and ballad-y of power ballads. A leftover from his solo debut that was recorded years later, in 1984, for a Jeff Bridges cheese-noir flick, “Against All Odds” gave the former Genesis man his first No. 1 hit in America.—Brent DiCrescenzo

Most heartbreaking lyric: “There's just an empty space / And there's nothing left here to remind me, just the memory of your face”

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