The 35 Best Breakup Songs Ever

Murder! Suicide! Murder-suicide! Here’s a compendium of pop’s most genius works of staggering heartbreak, with sentiments just caustic enough to make you consider sticking with dogs for companionship.

Brenda Kahn – “Mint Juleps and Needles” (1992)

Folk-punk singer-songwriter Brenda Kahn obviously knows a few things about shitty boyfriends (Creem once called her the “high priestess of the apocalyptic relationship”) and the dude she describes in “Mint Juleps and Needles” is a historic shitshow. He’s a frustrated, roiling alcoholic (from Boston!), not to mention that he’s already got a girlfriend. But that doesn’t stop Kahn from still pining away. Released on her major-label debut Epiphany in Brooklyn, “Mint Juleps” is a Dylan-worthy anthem for every woman who can’t stop herself from dating the worst guys.

OUCH: “Next to the club where your girlfriend is dancing on the bar / I left a stain on your glass, you called it a scar.” JULIE GERSTEIN

 

The Bevis Frond – “He’d Be a Diamond” (1992)

Most diehard ’90s girls will probably attribute “He’d Be a Diamond” to Mary Lou Lord, the subway busker-turned-indie singer who was rumored to have had an affair with Kurt Cobain. But Lord’s Kill Rock Stars debut is actually rife with covers, not the least of which is the Bevis Frond’s “He’d Be a Diamond.” Originally recorded on the Frond’s 1991 album New River Head, the song lambasts a lover who uses and abuses, while promising repeatedly that he’ll change. And sure, the song’s also been covered by Teenage Fanclub, but Frond’s original packs extra bite, thanks to singer Nick Saloman’s gentle sarcasm.

OUCH: “Is he lying to get what he wants or does he mean it this time? / Is he running low on affection and beer and dope / And an ironing board and an unpaid analyst who shags?” J.G.

Dixie Chicks – “Goodbye Earl” (1999)

It certainly wasn’t the first country ditty where a woman-beater gets his final comeuppance (see Martina McBride’s “Independence Day” or Kenny Rogers’ “Coward of the County”), but this is the most iconic; gaining its power from an infectiously dark comic sensibility (they poison his black-eyed peas) and some giddy, Springsteen-sized hooks. After radio stations got angry phone calls about the song’s infectious blood-thirst, the here-to-forever-controversy-prone Dixie Chick Emily Robison said in a statement, “We’re not promoting murder, and we even say that in a disclaimer on our album … Besides, is there a gentler way to go than with black-eyed peas?”

OUCH: “Ain’t it dark/Wrapped up in that tarp, Earl?” CHRISTOPHER R. WEINGARTEN

 

Ghostface Killah, feat. Ne-Yo – “Back Like That” (2006)

On his best-charting solo single to date, the Wu-Tang‘s most preternaturally emo MC explores his rage after his ex moves on to the next one — a jailbird and neighborhood snitch that Ghost has scuffled with in the past. The rapper was ten dusty fingers deep into his classic soul period, smoothly borrowing the despondent piano melody from Willie Hutch’s 1976 weeper “Baby Come Home.” “Back Like That” ironically flips a sweet love song to make a venomous one, but it’s definitely telling that both men are confessing that they’ve done somebody wrong.

OUCH: “Let me get that rock on your finger / Oh, it’s stuck? Then I’ll take the whole finger then, man.” C.W.

 

Buzzcocks – “Oh Shit” (1978)

Buzzcocks frontman Pete Shelley wasn’t going for an emotional exhumation here, just a snotty punk-rock kiss-off. The song, he has said, goes from “‘I’ve been dumped,’ to ‘It was your fault ’cause you’re shit.’ [It’s] all about the process.” Not exactly spiritual growth, but proof that lashing out childishly can be way more fun than picking through the ashes, searching for answers.

OUCH: “Oh shit, I wish I’d known before now / Oh shit, that you were such a fucking cow.” DAVID PEISNER

Miranda Lambert – “Kerosene” (2005)

Eleven years after Lisa “Left Eye” Lopes burned down Andre Rison’s mansion, this 21-year-old Nashville Star runner-up took the idea of a woman scorned turned human torch and built a career off it. (Steve Earle gets a co-credit ’cause the whole thing sounds like a straight cop of “I Feel Alright.”) The ex’s offenses are never detailed beyond the implication that he’s “holdin’ on to someone” else, but more to the point, this isn’t even about him. The act of arson seems less revenge than a shrug, idle hands turned destructive — what else is someone who’s giving up on love supposed to do all day? And that’s way scarier than revenge.

OUCH: “Light ’em up and watch ’em burn / Teach them what they need to learn.” STEVE KANDELL

 

Erykah Badu – “Tyrone” (1997)

Badu‘s boyfriend is cheap, selfish, oversexed, and it’s time for him to call his friend Tyrone and get some help packing his shit. This plainspoken live track (the real stars are the screams of affirmation from the audience) was supposedly spawned from a live improv in London, where Badu made up the lyrics as she went along. She’s said she “had no idea that it would make such an impact,” but “Tyrone” ended up setting the stage for the oncoming perfect storm of late-’90s scrub-bashing.

OUCH: “Every time we go somewhere / I gotta reach down in my purse / To pay your way / And your homeboys’ way / And sometimes your cousin’s way.” C.W.

 

Wilco – “Via Chicago” (1999)

Prior to 1999’s Summerteeth, Jeff Tweedy was widely seen as, if not a lightweight, then a generally genial presence, particularly compared to his ex-bandmate in Uncle Tupelo, Jay Farrar. Which is why the casual domestic violence permeating Wilco‘s third album was a surprise — even to Tweedy. “It’s just something that came out subconsciously, kind of free association,” he told Salon in 1999, regarding the homicidal musings of “Via Chicago.” “And it was like, ‘Wow, I’ve got to hang on to that one.’ It felt honest and close to something real.”

OUCH: “I dreamed about killing you again last night / And it felt all right to me.” S.K.

 

Amy Rigby – “Keep It to Yourself” (2002)

This criminally underrated chronicler of romantic disappointment outdoes herself on this track recorded live in Chapel Hill, North Carolina. Rigby has said she wrote the song after a new boyfriend asked her about her last relationship. “You say you’d like to kill the man who broke my heart,” Rigby coos gently over acoustic guitar and a swaying bossa nova beat, as the song opens. She goes on to essentially dare her current inamorato to off him, describing in acute detail where he can be found.

OUCH: “Here’s his address, here’s his picture, here’s the make and model of his car / He works until 4:30, then he hangs out at the topless bar.” D.P.

Afghan Whigs – “Fountain and Fairfax” (1993)

It’s hard to single out just one song off the Whigs‘ magnum opus of sex, lies, and betrayal, Gentlemen, but on this one, frontman Greg Dulli really lets the seething, slobbering, aggrieved beast within him roar. Over guitars that pierce like daggers, Dulli howls about the lover he sobered up for, only to discover that she’d been dishonest and unfaithful anyway. Dulli has described the album as “that point when things go wrong, when you get mean, thinking pretty shitty things.” You think?

OUCH: “It’s Tuesday now / I hear him breathing inside of her.” D.P.

 

Lucinda Williams – “Come On” (2007)

On this scorching takedown, the alt-country vet catalogs an ex-paramour’s numerous faults. But mainly, he’s a lousy lay. Williams has insisted this furious stomp started as a joke, but her withering assessment is probably not all that amusing to the target of her derision. “That person doesn’t know it was about him,” she once said, “and by the time he’s figured it out, it’s too late.”

OUCH: “You think you’re in hot demand / But you didn’t even know where to put your hand.” D.P.

Gary Stewart – “She’s Acting Single (I’m Drinkin’ Doubles)” (1975)

The singles discography of excellent ’70s honky-tonker Gary Stewart tells a familiar hard-luck story: First, he’s the sinner (“Drinkin’ Thing” and the cheating song “Out of Hand”); eventually, he hits the skids (“Ten Years of This,” “Quits,” “Single Again”). This hit, his biggest and drunkest, landed in the middle: “Truth is, I’m not man enough to stop her from doing wrong.” Amazingly, his actual marriage lasted from age 17 until 60 — when his wife succumbed to pneumonia. Then, two weeks later, Stewart shot himself.

OUCH: “While she pours herself on some stranger / I pour myself a drink somewhere.” CHUCK EDDY

Mendoza Line – “31 Candles” (2008)

Shannon McArdle has said she wrote and recorded this song before her then-husband and bandmate Timothy Bracy walked out on her in 2007, leaving only a note. But listening to this blistering first-person tale of a woman thrown over for a younger model “with a fucking kitty on her shirt,” you’ve got to believe she saw the writing on the wall. These Brooklyn indie rockers were always a three-ring circus of jealousy, self-loathing, and despair, but this song — in fact their entire final album, 30 Year Low — could double as court filings for McArdle and Bracy’s divorce.

OUCH: “Thought your package was for me / Christ, I should’ve known better / You couldn’t even face me / Wrote me in a letter.” D.P.

Jerry Reed – “She Got the Goldmine (I Got the Shaft)” (1982)

Guitar-slinging good ol’ boy makes country-chart-topping comeback with funky talking blues that reminds us old-timey minstrel jug-band stuff was rapping long before rappers were. On one hand, it’s Big & Rich two decades early; on the other, it’s a sad-sack men’s lib vaudeville routine about your wife leaving your suitcase on the porch, and what happens next: “They split it right down the middle, and they give her the better half.” In the real world, though, when Reed died in 2008, he’d been wed nearly half a century.

OUCH: “She’s livin’ like a queen on alimony / I’m workin’ two shifts, eatin’ baloney.” C.E.

Gilbert O’Sullivan – “Alone Again (Naturally)” (1972)

A working-class Irish piano man, clean cut in an emo-ready sweater decades before its time, flaunting his disinterest in rock’n’roll with his comic-opera-inspired stage name, gets stood up on his wedding day. So he questions God’s existence and considers diving off a tower, even as the church congregation heads home. Then he mourns the deaths of both of his parents. Depressing! And a No. 1 single for six weeks — not bad for a suicide threat. Years later, he got married anyway. And sued Biz Markie.

OUCH: “Climbing to the top / Will throw myself off.” C.E.

 

Freddie Gibbs – “Queen (Luv U 2 Death)” (2009)

Gibbs sets us up here: The first two minutes of this twisted, three-minute tale are an earnest paean to the woman who is his port in a storm — “my only friend, the only one I can trust.” Then the couple gets robbed, and the rapper discovers it was a setup: His “French vanilla butter pecan chocolate deluxe” has been creeping around with his assailant. So Gibbs does the only logical thing he can in a song like this: He shoots her.

OUCH: “I was down to give my life for you / Wife-ing you / Love you from the start / Stankin’ ass bitch, you breakin’ my heart.” D.P.

Tonio K – “H-A-T-R-E-D” (1978)

Journeyman songwriting pro Steven Krikorian begins the final track on his crazed first album, Life in the Foodchain, in sensitive, soft-rock, singer-songwriter mode warbling about just another love affair gone bad, with a laid-back drawl that’d never get him kicked out of Hotel California’s swimming pool. Then he suddenly yells out, “Eins, zwei, drei, vier!” and everybody turns into the Sex Pistols. “I wish I was as mellow as, for instance, Jackson Browne,” muses Tonio, “but ‘Fountain of Sorrow’ my ass, motherfucker, I hope you wind up in the ground.”

OUCH: “I’m going to K-I-L-L one of us, baby, give me time and I’ll decide on which.” C.E.

Mr. T Experience – “New Girlfriend” (1994)

While the Ramones’ bitterest love song (“Glad to See You Go”) used Charles Manson as an absurdly glib punch line, the Bay Area pop-punks of the late-’80s and early ’90s who inherited the gabba gabba groove gave heartbreak a headier, more bittersweet lilt (that was no less relationship-whipped). Perhaps the best example is Mr. T Experience‘s ruthless-seeming rejoinder to an old girlfriend, with singer-songwriter “Dr. Frank” Portman mocking her by trumpeting the awesomeness of his new girlfriend, who bakes pies and knows which fork to use and sits around with him while he, um, talks endless shit about his old girlfriend?! It all falls apart when he stoops to the pitifully dorky retort that “you made a fool of me, but who’s laughing now and who’s laughing not, HA HA HA HA HA HA HA HA.” Sheesh, just go and have a wank already, Skeezix.

OUCH: “My new girlfriend is better than you / She’s got higher breasts and a bigger IQ.” CHARLES AARON

Scrawl – “Vi Ploriontos” (1991)

Leading off the female indie-punk trio‘s Bloodsucker EP, and given an extra shiv of bitterness by label troubles, “Vi Ploriontos” is lean, mean, and leaves a discordant farewell shot of “You’re gonna cryyy!” clanging around your skull. Singer-guitarist Marcy Mays was some kind of genius diarist of what it’s like to tolerate (and then not) codependent drunk assholes; and here, she’s almost lost in a revenge trance while the band bashes away in full support. Their rollicking cover of Paula Abdul’s “Cold Hearted,” on the same EP, bites down hard on the word “snake,” as one might imagine.

OUCH: “I wasn’t worth a Megadeth ticket, a shave, a fine wine…Though