breakup songs
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15 Breakup Songs That Are Vicious, Painful, and Bitter

A friend requested a hopeful, forward-thinking breakup playlist to help soothe their pain. We send these 15 bitter breakup songs instead.

There are breakups, and then there are BREAKUPS. Vicious, hateful, never-wanna-see-you-again conflagrations; searing romantic firestorms with no time for sweeter memories. The stronger the love, the greater the flame-out. Misery loves company, too, so a truly shattered heart demands catharsis – talented musicians spilling their guts and sharing our pain.

Some of these pop song relationships are already done for, while others writhe in their death throes. Failure, rejection, and abuse abound, spiced with (lyrical) murder and suicide where necessary. No sappy reconciliation or regret allowed because we’ve all been there.

Valentine’s Day is over, and business is business. So, bring on the vitriol with these breakup songs.

15. Ace Frehley – “Rip It Out” (Ace Frehley – 1978)

Ace Frehley’s electrifying 1978 solo debut has only grown in stature for many music buffs. Along with paeans to drugs and endless alcohol, the romantic entries on Ace Frehley derive from sincere love/hate experiences as well. Innocent ten-year-olds may not have appreciated the venom spewing from opener “Rip It Out”, but we sure do now: “Rip it out, take my heart… I hope you suffer!KISS’ spotty solo releases were the beginning of the end for the original foursome. But five decades on, Ace’s ode to fundamental rock-and-roll lingers still.


14. Single Gun Theory – “My Estranged Wife” (Flow, River of My Soul – 1994)

This toxic male is as receptive to feminine indie-pop as anybody else despite sometimes running too syrupy for its own good. Single Gun Theory’s third and final 1994 studio release, the uber-passionate Flow, River of My Soul, is a gut-wrenching document of emotional devastation. The record signaled a drastic shift for the Aussie band, who toned down their generic dance beats for rolling, jazz-tinged innovation.

“My Estranged Wife” remains a legitimate soul-crusher, with murderous piano lines and bummer lyrics like “The heaviness of the clouds reflects / The condensation inside of me…” Companion track “Fall” got some college radio airplay, making Flow’s grueling experience well worth seeking out.


13. The Dead Milkmen – “Silly Dreams” (Soul Rotation – 1992)

Unlike most fans, 1992’s Soul Rotation is my favorite Dead Milkmen release. While 1988’s Beelzebubba boasted their two best tracks, Rotation proved their most consistent record from start to finish. “Silly Dreams” somehow derives romantic poignancy from kiddie-show keyboard riffs and repulsive kindergarten images, like cats vomiting and dirty rags beneath the sink. Mercifully, these are just silly dreams, and in the end, our decrepit narrator wakes up with his lover still beside him. But whoops! Unfortunately, that’s a dream, too – she’s a thousand miles away.


12. Too Much Joy – “Sort of Haunted House” (Mutiny – 1992)

Here, we swerve from sophisticated fem-pop to snide frat-rock. Too Much Joy’s main claim to posterity was a 1990 sympathy arrest for playing 2 Live Crew songs onstage during that era’s music-censorship lunacy. The band released three decent college-rock records in a row, including 1992’s Mutiny.

The terminally sick “Sort of Haunted House” describes ‘a ghost in every room’ – the ghost being our narrator’s flame, found in flagrante delicto with her lover and subsequently dispatched from this earth. “Scrubbed the floor, but the bloodstains settled in… Swear to God, I aimed the gun at him!” “Haunted House” is a morbid killer’s treat, culminating with the narrator’s hopeless suicide. Sunshine and lollypops all around!


11. Billy Idol – “Eyes without a Face” (Rebel Yell – 1983)

Every so often, a successful yet uneven artist releases a track so extraordinary, so shockingly superior, that even haters are forced to take notice. That is precisely what happened when former Generation X frontman and MTV video darling Billy Idol released his “Eyes without a Face” single in June 1984. This achingly gorgeous ballad is suffused with homicidal undertones and one of pop’s most unexpected ripping solos by guitarist Steve Stevens. In his memoir, Idol claims the song is about “a relationship gone wrong, on the edge of disintegrating into madness”. As for why the most outstanding art derives from such nether regions of suffering and disrupted passion, we’ll leave that for another time.


10. Poster Children – “New Boyfriend” (Junior Citizen – 1995)

There’s an irrepressible petulance to Junior Citizen’s 11 tracks, like garish late-night anime on steroids. We recently had the privilege of interviewing Poster Children’s Jim Valentin, who revealed an aspect of the biting, faux-violent “New Boyfriend” we never quite picked up on. “I try to write misleading songs, where I paint part of the picture, and you paint the rest,” he says. “The line ‘Really hate your new boyfriend’ sounds superficially angry, but my intent was to slowly reveal that the narrator himself is a jerk. That’s why there’s a new boyfriend. Duh!” Fans still request the song in concert, rushing to the stage and dancing to it.


9. Warren Zevon – “The French Inhaler” (Warren Zevon – 1976)

It is our contention that 1970s troubadours like Harry Nilsson, Gordon Lightfoot, and Warren Zevon lived, loved, and partied harder than all but the most degenerate rock acts of the era. The strongest track on Zevon’s justly revered 1976 touchstone may be “The French Inhaler”, about an ex-girlfriend Zevon saw with another musician after their breakup. This kind of aching lament paralyzes the listener at first impression, elevating the entire album around it. Zevon’s transcendent bridge contains one of our favorite all-time lines: “I drank up all the money”. Drop the mic, Warren! Who else comes up with a line that damn good?


8. ‘Til Tuesday – “Voices Carry” (Voices Carry – 1985)

Credit this one’s staying power to Aimee Mann’s indelible MTV video performance, bringing her anguished frustration home to millions of viewers. Forty years later, 1985’s “Voices Carry” remains a control freak’s sonic nightmare. Mann penetrates her detached lover’s psyche as deeply as she can, which is not at all. Instead he admonishes her to ‘keep it down’, prompting the public auditorium cri de coeur every member of Gen-X still considers our own. There may be two sides to every story, but Mann’s Hulk-like eruption during “Voices Carry’s” denouement leaves room for only one.


7. Genesis – “Misunderstanding” (Duke – 1980)

This reviewer considers GenesisDuke one of the great underappreciated albums of that transitional decade. Duke’s lead character has been described as an Everyman figure, a lonely and vulnerable individual who experiences life’s ups and downs much like anyone else. “Misunderstanding’s” offhand repudiation thus hits home for all of us, proving the opposite of love is not hate – it’s icy indifference.

Each dismissive layer of feeling is laid bare, from the height of ecstasy (“Never dreamed I’d have this feeling”) to the pit of desperation (“Waited in the rain for hours”). Couching such wretchedness inside a fabulous pop song never hurts, either. Why is the ghost of attraction so fleeting and romantic disappointment so unbearably cruel?


6. Lloyd Cole – “Are You Ready to Be Heartbroken?” (Rattlesnakes – 1984)

Lloyd Cole remains one of pop music’s most astute chroniclers of dating and relationships, and this slinky gem has been interpreted at least a million ways. The title and chorus (“Are you ready to bleed?”) yield the merest inkling of the torment this song can transmit. Yearning strings lend Cole’s pensive acoustic riff a deathless impact, while his lyrics perfectly encapsulate the saying “depression equals distraction”.

The listener’s initial status forever dictates their opinion of “Are You Ready to Be Heartbroken”. Did you first hear it while happily married or suffering from an exquisite heartbreak? Till the end of your days, for better or worse, “Heartbroken” will recall that precise mindset. Given this list’s theme, we hardly need to recount our own impressions.


5. Gordon Lightfoot – “Sundown” (Sundown – 1974)

Our lone US number-one chart hit and one of the first songs this writer ever learned by heart. Gordon Lightfoot’s deceptively spare “Sundown” sounds innocent enough until you hear the chilling backstory. Then it’s dark, darker, darkest. Lightfoot’s folksy touch was always manifest, and he had a charming knack for seductive lullaby melodies.

Fraught with jealousy and incapacitating paranoia, “Sundown” was supposedly written about backup singer and then-girlfriend Cathy Smith. Whatever detriment she may have been to Lightfoot’s sanity, her effect on John Belushi was far worse – it was Smith who injected him with the coke/heroin ‘speedball’ that took his life in 1982. For his part, Lightfoot lived to the ripe old age of 84, delivering an all-time classic in the bargain.


4. Sugar – “A Good Idea” (Copper Blue – 1992)

At our 1992 college reunion, all anyone could talk about was Bob Mould’s new Sugar album, Copper Blue. “A Good Idea” has long been our ferocious favorite, a lethal tale of impulsive (and likely consensual) romantic violence. Did she ask for it or not? Is it all in his head? We’re never quite clear whether the killer and victim are even dating, let alone in love. But the result is unforgettable – a grotesque tale of savage temptation. Most embarrassing of all, it’s one of few tracks that compel this reviewer to unabashedly strum his air guitar. And we don’t care who knows it.


3. Ned’s Atomic Dustbin – “Not Sleeping Around” (Are You Normal? – 1992)

It’s difficult to describe the backbreaking, adrenal-gland rush “Not Sleeping Around” still provides, even thirty years later. Kaleidoscopic layers, blinding riffs, otherworldly machine-gun drumming as the antithesis of four-time rock: This was the song that weaned so many of us off “Teen Spirit” and similar grunge prototypes.

For Are You Normal’s 30th anniversary, we confronted lead singer Jonn Penney about brutal lines like “You keep thinking I’m tired of you / But I’m just tired!” What remorseless she-devil were these hateful missives directed at? Answer: Nobody. Unlike most of us, Penney has been with the same partner since 1990 and wrote about other people’s relationships. To this day, “Not Sleeping Around” still feels like an exhilarating shot across rock’s bow that hasn’t quite landed yet.


2. The Smithereens – “Only a Memory” (Green Thoughts – 1988)

This bitter bombshell holds a special place in our shattered hearts. The Smithereens’ “Only a Memory” can easily harsh any nostalgic mellow, occupying a doleful class alone. Produced by 1980s indie maestro Don Dixon, that ineffable car-crash riff grits the teeth like few others in rock, spiking the blood pressure before Pat DiNizio’s heartsick lyrics even kick in.

According to Wikipedia, the band’s roadie had his pocket tape recorder handy when DiNizio came up with the introductory chord, and thank heaven for that. Subtlety may win plaudits, but in an industry rife with pulled punches, the Smithereens land every fist ever thrown. Most of these breakup sagas chronicle anger and loss; “Only a Memory” laments the tragic agony of waste.


1. The The with Sinead O’Connor – “Kingdom of Rain” (Mind Bomb – 1989)

“All the love we’ve got to give / Has all spurted out.” So sings Matt Johnson, whose “Kingdom of Rain” is the ultimate eulogy to the death of love. Pounding rain and “Riders on the Storm” thunderclaps underpin Sinead O’Connor’s duet vocals, transforming the song into a resigned cross-examination of failed acrimony. So much vituperation directed against a former flame – and she completely agrees with him!

Genuine horror arrives when we realize this doomed couple will probably keep hating and dying together forever. Only once or twice has this writer felt such resentment toward another human being, particularly while lying beside them in bed. More like a vile Egyptian curse than a pop song, this gruff slice of raw oblivion makes us never want to date again.


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