The 25 Greatest Breakup Songs of the 1980s

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The 25 Greatest Breakup Songs of the 1980s

We've been looking so long at these pictures of you.

We recently assembled the greatest love songs of all time, but let's face it: while love has inspired some great songs, the majority of classics come from a darker place. Our rules this time were simple: a breakup song can be vengeful, dignified, devastated, or whatever else, as long as the lyrics make explicit reference to a relationship that is ending or has ended. Again, we limited it to one song per songwriter (not necessarily per band). Come back next week for the best breakup songs of the '90s, and let us know what we missed in the comments. Also, feel better. You're going to get through this, and to help with that, here's a Spotify playlist of this week's list, and here are the greatest breakup songs of the '60s and '70s. — The Hooksexup Editors

25. Paula Abdul, "Cold Hearted" (1989)

You will dance through this. You will find someone better. Paula Abdul commands it, and the beat enforces it. Resistance is futile. — Alex Heigl


24. The B-52s, "Give Me Back My Man" (1980)

This surreal dance track tones down the usual zaniness of the early B-52s (no Fred Schneider on this one at all) for a weirdly devastated story with lyrical echoes of a sea shanty. For maximum tragic effect, check out this video; Cindy Wilson's frail-little-girl delivery makes the song all the more haunting. — Peter Smith


23. Jackson Browne, "In The Shape Of A Heart" (1986)

Apparently written about the suicide of Browne's first wife, "In The Shape Of A Heart" came out ten years later, and it has the feel of melancholic reflection at a distance. Browne sets up a romantic story about a heart-shaped pendant, then neatly inverts his song title for a grown-up, world-weary assessment of love and the unknowability of the other: "You try so hard to keep a life from coming apart / And never know what breaches and faults are concealed in the shape of a heart." Brutal. — P.S.


22. Tracy Chapman, "Fast Car" (1988)

"Fast Car" is one of the most crushing songs ever written about cyclical poverty, but it's also a haunting portrait of an aspirational partnership gone sour. The song's final kiss-off is painful — Chapman sends her man on his way, wanting more for him, but it's with the full knowledge of how trapped she really is. — A.H.


21. Tom Waits, "Hang Down Your Head" (1986)

Cowritten by Waits' wife, playwright Kathleen Brennan, "Hang Down Your Head" is one of Waits' most tender songs, capped off by a lyrical Marc Ribot guitar solo. (It's a rare instance of Ribot not attempting to strangle his guitar.) Playing into Waits' obsession with the archaic, it tells the the oldest breakup story in the book: "You have found another, oh, baby, I must go away." — A.H.


20. Chris Isaak, "Wicked Game" (1989)

This song has one of the sexiest videos of all time, and that weird Elvis-aping hiccupy vocal tic is undeniably catchy. Isaak's vocal and and James Wilsey's guitar licks are live, but the rhythm tracks are loops constructed from previous takes — the way they push against each other is a little disorienting, and that gives the song a loose feel that perfectly paints a boozy night of regret. — A.H.


19. Janet Jackson, "Come Back to Me" (1989)

So much of Rhythm Nation is so stern and authoritative that when "Come Back to Me" drops, it's hard to believe this is our Dear Leader dropping her guard to plead with a departed lover. That juxtaposition makes it all the more effective, and all the more moving. — A.H.


18. Hüsker Dü, "Don't Want To Know If You Are Lonely" (1986)

With text messages and voicemail replacing the answering machine, the feeling of ignoring a call while listening to someone leave a message is gone forever. In ten years, your average post-grad will never know the feeling of listening to a 4 a.m. message come in from a recently departed boy/girlfriend. Luckily, they'll have one of the best Hüsker Dü songs to commemorate the experience. — Sean Morrow


17. Bob Dylan, "Most of the Time" (1989)

"Most of the Time" beautifully captures that nagging little voice inside your head that sneaks up on you at the most unexpected moments. "Don't even remember what her lips felt like on mine" — damn it, Bob, yeah, you do! — J.G.


16. REM, "The One I Love" (1987)

Here's a classic of the "frequently misinterpreted lyrics" genre. Michael Stipe says "The One I Love" is about "using people over and over again." In that sense, this is about not only giving up your lost love, but your own terrible habits as well. — J.G.


15. New Order, "Age of Consent" (1983)

In an angsty moment, count on a great keyboard riff to make you feel like it's going to be okay. See "Age of Consent." At once calming, classy, and catchy, this is a requiem for a mostly-adult relationship. Maybe the Brits are just more composed than us, but, while cutting, "Age of Consent" also sounds almost polite. — Rachel Krantz


14. Echo and the Bunnymen, "Bring on the Dancing Horses" (1985)

If a loved one had woken up from a ten-year coma on January 1st, 1990, and asked what the '80s sounded like, I might've played them "Bring on the Dancing Horses." A perfect piece of shimmering '80s pop, it's also a surreal pre-mortem for a coming breakup. Ian McCulloch expresses guilt about the heart he's about to break, but the music sounds like relief and rebirth. — S.M.


13. Billy Bragg, "Must I Paint You a Picture" (1988)

"A New England" is a great song, but "Must I Paint You a Picture" is one of the most moving, accurately sketched portraits of a relationship killed by overthinking: "The temptation to take the precious things we have apart to see how they work must be resisted, for they never fit together again." Ouch. — A.H.


12. The Jesus and Mary Chain, "Just Like Honey" (1985)

With brutal honesty, "Just Like Honey" describes what runs through your brain when you find yourself back with the person who can only be described as a total life ruiner: "I'll be your plastic toy." It'll give you that desperate moment of clarity you need if you find yourself making all the wrong choices. — J.G.


11. The Replacements, "Answering Machine" (1984)

The Replacements were notorious for sandwiching heartbreakers like this between ludicrous pisstakes. On Let It Be (even that title!), "Answering Machine" follows closely on the heels of something called "Gary's Got A Boner." No matter; the band's flippant side actually throws the vulnerability of songs like "Answering Machine" into sharper relief. Over an intricate guitar figure, Paul Westerberg yearns to reconnect to a distant girlfriend, but it's clear she's slipping away. — P.S.


10. Dire Straits, "Romeo and Juliet" (1980)

Unlike whatshisface's play, this "Romeo and Juliet" suggests that love can end in tragedy without anyone getting poisoned. The implied contrast to a legendary romance makes Mark Knopfler's breakup sound all the sadder. — S.M.


9. The Ramones, "The KKK Took My Baby Away" (1981)

Some say Joey Ramone wrote this song about Johnny Ramone stealing away his girlfriend; others dispute the story. Whatever; most Ramones songs are nonsensical, but this one is also totally awesome. After a rough breakup, you might actually be comforted to think that your ex was kidnapped by racists, rather than leaving you of her own free will. — J.G.


8. Human League, "Don't You Want Me?" (1981)

Unlike almost every other breakup song ever written, "Don't You Want Me?" gives us both sides of the story, featuring the lead singer, Philip Oakey, dueting with bandmate Susan Ann Sulley. Together, they give us arguments from the spurned and the spurner. But victory goes to the shout-along chorus, which surely anyone can relate to. — J.G.


7. Elvis Costello, "I Want You" (1986)

This must be the most intense thing that Elvis Costello ever recorded. It's like he's trying to scare the girl into coming back to him under the penalty of some kind of love-knifing. Spitting out lines like "I might as well be useless for all it means to you," he captures the bitterness of a breakup perfectly. — J.G.


6. Soft Cell, "Tainted Love" (1981)

Originally performed by Gloria Jones in the '60s, "Tainted Love" got a new life from Soft Cell's danceable, synth-heavy remake. Fittingly for a tune about trying to get out from under someone's spell, it's almost impossible not to sing along. — R.K.


5. The Cure, "Pictures of You" (1989)

"Pictures of You" is so devastating because it perfectly nails the mixed feelings of reminiscing about a past relationship — how we return to certain memories time and time again until they take on life of their own. "I've been Facebooking for so long at these pictures of you" doesn't have quite the same feel, but the sentiment is still the same. — A.H.


4. Willie Nelson, "Always On My Mind" (1982)

The apology song is a difficult one to pull off — if the song is too self-flagellating, it becomes more about the singer than the person they've wronged. But Willie Nelson gives "Always On My Mind" a perfect balance of regret and resolve. His sandpapery rasp and restrained delivery are the real reason this song — covered by so many others — belongs to him. — A.H.


3. Paul Simon, "Hearts and Bones" (1983)

Conventional wisdom probably gives the nod to "Graceland" (a great one, no doubt), but we've got to go with "Hearts and Bones," an ambivalent masterpiece about Simon's troubled marriage to Carrie Fisher. These two very different people "return to their natural coasts," but a complex, difficult connection remains: "You take two bodies and you twirl them into one — their hearts and their bones — and they won't come undone." Both tender and sharp, "Hearts and Bones" might be the greatest lyric Simon's ever written. — P.S.


2. Prince, "When You Were Mine" (1980)

The perfect craft of "When You Were Mine" might conceal the hurt at its core. No one would blame you for getting distracted by the huge guitar, vocal, and keyboard hooks — or by the revolutionary-for-its-time gender ambiguity of the narrative. But under all that is a simple, biting observation about human nature: "I love you more than I did when you were mine." — P.S.


1. The Smiths, "I Know It's Over" (1986)

"I Know It's Over" finds the normally self-obsessed Morrissey stunned into a place of universal compassion. A breakup has rendered him vulnerable to the point of fetal ("The sea wants to take me/ The knife wants to slit me"), but he finds a way to a profound insight: "It's so easy to laugh, it's so easy to hate/ It takes strength to be gentle and kind." Over nearly six minutes, he touches on nearly every aspect of breakup psychology. The song is vast, chilling, and completely devoid of The Smiths' usual winking. — P.S.


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