The 50 Best Breakup Songs of All Time

The best heartache a half-century of music can provide.

by Nerve

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: one, 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. Two, we limited it to one song per principal songwriter. Three, this list goes back to 1960, which we feel represents the dawn of pop music as we know it, but we apologize to Edith Piaf, Frank Sinatra, Mozart, et al. Okay, now you can tell us what we missed. Have fun, and be sure to check out this Spotify playlist of our picks. — The Nerve Editors

 

50. Kelly Clarkson, "Since U Been Gone" (2004)

Obnoxious text-speak aside, this is how you build a pop song. Clarkson's voice starts out low, the drums sound like a Casio keyboard, and you're wondering what's so great about this club and why you've been dragged here when you just want to sulk at home. Then that chorus decks you in the face, and before you know it, you've had four shots because you're so fucking fierce and you don't need him (or her), you don't need anyone and you're jumping around like an idiot... and here comes that chorus again! — A.H.

 

49. 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.

 

48. The Buzzcocks, "Ever Fallen In Love... (With Someone You Shouldn't've)" (1978)

Of the great early punk bands, only The Buzzcocks were predominately concerned with love. "Ever Fallen In Love" has a weary fatalism that belies the fact that it was written by a twenty-three-year-old. Having fallen in love with the wrong person, the singer finds himself completely at her mercy; he doesn't seem to get a vote in things. — P.S.

 

47. Dolly Parton, "I Will Always Love You" (1974)

Forget everything you ever knew about Whitney Houston's version of this song. You can hear the heartbreak in Dolly Parton's voice as she gracefully ducks out of a tumultuous relationship. There's something comforting about the dignity the song finds in ending a relationship peacefully, even if things are usually a lot messier in real life. — J.G.

 

46. Wilco, "I Am Trying to Break Your Heart" (2002)

Jeff Tweedy often seems to be trying to obscure his emotional songwriting with avant-garde touches like weird ambient sounds, deliberately "wrong-sounding" notes, and obtuse lyrics. But none of those elements can stop "I Am Trying to Break Your Heart" from succeeding in its titular aims. — A.H.

 

45. 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.

 

44. 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.

 

43. The Temptations, "I Wish It Would Rain"

While "I Wish It Would Rain" is about a man hoping for inclement weather to hide his tears because "a man ain't supposed to cry," I suggest ignoring that somewhat dated sentiment and thinking about those gloriously self-absorbed days we all have after a breakup, when we wish the rest of the world would feel as dismal as we do. Then put this song on and let David Ruffin sweep you into a world of heartbreak. — A.H.

 

42. Weezer, "Butterfly" (1996)

Closing out a near-perfect album of guilt and angst, "Butterfly" is a devastating story about the guilt of being unable to commit. Totally exposed, Rivers Cuomo confesses to having hurt someone who didn't deserve it. He tries to figure out why he did it, but in the end, all he has are two plaintive words: "I'm sorry." — P.S.

 

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

This must be the most intense song 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.

 

40. 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.

 

Commentarium (90 Comments)

May 29 12 - 12:50am
UHF

Nice choices, but where is "The Winner Takes It All," "Careless Whisper," "Against All Odds" and "Walk on By?"

May 29 12 - 2:10am
steve

#162, #401, #795, and #924, respectively.

May 29 12 - 2:14am
Yabba

A good list, but I would like to have seen Roxy Music represented, either by "A Song for Europe" or even better, by "Just Like You."

Jun 04 12 - 3:52am
yonsito

or "dance away" perhaps?

May 29 12 - 2:15am
JCHH

Gotta say, this Spotify crap really sucks ballz for your international readers who can't access it.

May 29 12 - 11:23am
Josh Rice

Ahh, that explains all the missing songs...except that I'm in the US and they aren't showing up. Please stick with your regular player!

May 29 12 - 12:04pm
person

they have the regular mp3 embeds. the spotify is just for all of the songs collected in one playlist.

May 29 12 - 2:52am
p4k

Ms.Jackson at #3 ?
You shittin' me.

May 29 12 - 5:47am
Where is it???

DONT LOOK BACK IN ANGER

May 29 12 - 8:07am
blahblah

In the trashcan.

May 29 12 - 8:52am
Spare Parts

Bruce Springsteen "Drive all Night"

May 29 12 - 10:21am
Bruce

Little Red Book, by Love. a great version of a Bachrach-David song. Total classic.

May 29 12 - 10:57am
BelovedMonster

It may be new(ish), but Weights and Measures, by Dry the River, deserves consideration.

May 30 12 - 7:55pm
OH

Just that whole album.

May 29 12 - 11:26am
mk

I humbly submit that "Shame," by the Avett Brothers, is a very good breakup song.

May 30 12 - 12:43pm
Alex Heigl

+ 1.

May 29 12 - 12:15pm
jt

excellent writing...short and sweet.

May 29 12 - 1:51pm
GG

Why Mireille Mathieu's version of Ne Me Quitte Pas was not used is beyond me...

http://www.youtube.com/watch?v=G324yjbvI-4

May 29 12 - 3:28pm
GeeBee

I used to so have the hots for her in the late 70s!

May 29 12 - 4:03pm
GG

Haha, I totally understand and could never get past the hair...well, that and her uncanny resemblance to my ex's mother.

May 29 12 - 3:45pm
GeeBee

Harry Nilsson so deserves to be in the top 5 with "Without You" though he didn't write it (I just found out) but did write the almost as wonderful "Without Her", recorded by Blood Sweat and Tears.

May 31 12 - 9:08pm
tmjm

Nilsson's version of "Without You", like "Nothing Compares 2 U" is another one of those songs where the cover vastly eclipses the original. (Jeff Buckley's "Hallelujah" is another.) But the tragic back-story of Badfinger makes their original version of "Without You" pretty compelling, even it took Nilsson to wring every drop of heartbreak out of the song.

May 29 12 - 4:00pm
Mitch

Don't Speak and Ms. Jackson need to switch places, plz.

May 29 12 - 4:04pm
z

in dreams is great, but all i think about is the scene in Blue Velvet... I would say Crying would be a better choice...

May 29 12 - 5:11pm
Kbabe

My number one is 'Whydya do what you did?' by Marianne Faithful. It perfectly expresses the angry of finding out your lover has cheated on you.

May 30 12 - 1:06pm
GeeBee

Ah but you really think Nerve in its currently moribund incarnation is going to cite a song with "cunt" in the lyrics? Awesome awesome song though. I will have Marianne (another woman I had the hots for at an early age!) on rotation all day at work. Earbuds time!

May 30 12 - 1:53pm
PeterSmith

That is true; in our ongoing effort to stave off impending death, we carefully scanned each of these tracks for the presence of the word "cunt." I think we're safe now, though.

May 29 12 - 6:51pm
eg73

You said "titular".
And "Don't Speak" is the most hideous song ever written.

May 31 12 - 2:34pm
gd

Nah, it's not even the most hideous song on this list. I can't listen to Macy Gray without thinking "If this is playing here, what's playing in Hell?" I HATE her voice and that song.

May 30 12 - 7:22am
dsgsd

If you're going to put Ne Me Quitte Pas in then it has to be the original
http://www.youtube.com/watch?v=za_6A0XnMyw

Jun 14 12 - 6:30pm
Graham Clark

^ What he said.

May 30 12 - 12:40pm
ftu

How about Rejazz from Regina Spektor? It sure deserves a place on this list, if not the N°1

http://www.youtube.com/watch?v=LoGFQ0AcXmc

May 30 12 - 3:56pm
res

once again, Nerve, you forced me to go through this entire list when I knew that you guys are too stupid to remember to put "The Breakup Song" by the Greg Kihn Band in the list. And you didn't disappoint. Really, you guys are just idiots. "THE BREAK-UP SONG"! what the fuck do you think that's about????? Just idiots....

May 31 12 - 11:17am
Alex Heigl

We know what it's about. And we're not "too stupid to remember." We just don't like it that much.

May 31 12 - 1:43pm
Nicolas

Great list! I was a little bit sad you guys didn't include any of Beck's songs from Sea Change, whatever. Loved the Joni Mitchell addition. Thanks!

May 31 12 - 3:38pm
PeterSmith

Thanks, Nicolas! Beck only just barely missed the cut.

May 31 12 - 5:15pm
larson 400

the end - the doors

May 31 12 - 6:32pm
Joseph

Spiritualized - Ladies and gentlemen we are floating in space

If this isn't the most epic song about heartbroken lovesickness, then I don't know what is.

May 31 12 - 6:56pm
MrFlagg

What about "The Break Up Song"? or is Kihn not hipster enough?

May 31 12 - 8:33pm
Cure fan

OK, I gotta say that Pictures of You is not the best breakup song by the Cure. That honor goes to Play for Today & its angry, snotty brilliance.

Jun 26 12 - 3:52pm
JohaN

or even just plain old "Boys Don't Cry"... (not to mention about a third of Wish...)

May 31 12 - 9:03pm
tmjm

Um, if you're going to call your list the 50 greatest breakup songs of *all time*, the failure to include anything by Hank Williams is inexcusable. "Cold Cold Heart" and "Mansion on the Hill" should be in the top 10, and "Your Cheatin' Heart" can't be anything but number 1.

Just go listen to them.

May 31 12 - 9:42pm
tmjm

Oops, missed your disclaimer re 1960. Seems a bit arbitrary though.

Jun 04 12 - 12:45pm
Alex Heigl

Well, it's just that pre-1960 music is just such a can of worms. Edith Piaf, Frank Sinatra, Hank Williams, Tin Pan Alley, early Chess Records, not to mention Beethoven, etc... Where do you draw the line?

May 31 12 - 9:10pm
x

Again?! Given that it a major oversight to leave "You Oughta Know" out of 90s list, I was hoping you would man up , admit your mistake, and give Alanis her rightful place on this list. I'm am even more disappointed then I was the first time you wronged me. Luckily I can think of a song that matches my outrage...

Jun 04 12 - 12:48pm
Alex Heigl

Well, you're not alone. Plenty of readers were upset at that omission. But we stand by our decision.

May 31 12 - 9:11pm
Steve

Dusty Springfield - I Don't Want to Hear It Anymore

May 31 12 - 11:30pm
G

Ms. Jackson reminds me of "Sylvia's Mother" by Dr. Hook, a phone call intercepted by, well, Sylvia's mother.

Jun 01 12 - 2:45am
dabayner

Sometimes Love Just Ain't Enough--Patty Smith. Clearly, this song belongs on this list.

Jun 01 12 - 4:46am
calman

How could Roy Orbison's "Crying" have been left of the list?

Jun 01 12 - 8:02am
Greg

Foo Fighters
"Let It Die"

Jun 01 12 - 8:20am
alp

"I can't make you love me" by Bonnie Rait has got to be in the top 5. It's heartbreaking and perfectly captures a situation we'be all been in.

Jun 01 12 - 7:43pm
Audrey B

You are absolutely right on this one, there is a heartbreaking - raw - honesty in that song. It truly captures the inevitable truth of a breakup.

Jun 01 12 - 8:41am
Finder (Richard)

for a breakup song that rips your guts out, you won't find better than Airborne Toxic Event's "Sometime Around Midnight". It captures the devastation of seeing an old lover again, perfectly. First time I heard it I couldn't stop thinking about it, and hearing that register-leaping cry of anguish, all day.

Jun 01 12 - 8:49am
Finder (Richard)

@alp
and what about "My First Night Alone Without You" (Bonnie Raitt)? There's a hard-core breakup song if I ever heard one.

Jun 01 12 - 1:39pm
Lisat

My favorite is the Romeo and Juliet. I'm surprised it's on here since it was never a radio hit. Great list. I would add Boys of Summer by Don Henley. I know it was overplayed but it's a classic breakup tune. Roy Orbison's crying??? I used to cry to that song before I fell in love (16 yrs old)

Jun 01 12 - 7:28pm
Audrey B

Cindy Lauper's version of "When You Were Mine" adds quite a layer to the song. Worth the comparison and in my opinion, better.

Jun 01 12 - 8:01pm
Elan

I was stunned The Temptations "I Wish it Would Rain" wasn't in the top ten. When my mom told my dad she wanted a divorce, he sang that song to her at karaoke that night and looked straight at her the entire time. Saddest thing I ever saw, and my dad has a killer voice.

Jun 04 12 - 12:46pm
Alex Heigl

Whew. That's heavy.

Jun 02 12 - 4:36am
LT

I am suprised there was no Jim Croce... One less set of footsteps.. Operator... Photograps and memories

Sep 15 12 - 5:06am
Tucker

Croce has a catalog full of them. 'Footsteps' is perfect. Also, 'Next Time, This Time' or 'Lover's Cross'.

Jun 02 12 - 10:08pm
k

no adele? really? someone like you has to be the one of the greatest.

Jun 04 12 - 12:47pm
Alex Heigl

Missed the date deadline -- came out in 2011.

Jun 04 12 - 3:02pm
Kalkaino

I dunno. Beatles: "You've Got to Hide Your Love Away" beats "For No One" handily.
Stones' "Let It Loose" blows away the rather treacly and clunky "Angie." Also too "Love in Vain."
And you guys never heard of say, Steve Earle, Patty Griffin, John Hyatt? Ranking breakup songs without 'Nashville inflected' writers is kinda like rating top fifty wines without any French ones.

Jun 14 12 - 6:28pm
Graham Clark

There are many Rolling Stones break up songs compared to which "Angie" could be said to sound 'treacly and clunky'. ("Ruby Tuesday" and "No Expectations", to name two.)

"Let It Loose" is not one of them.

Jun 04 12 - 3:36pm
Dangeroso

Isn't that a Gallagher brother in the Beatles pic?

Jun 04 12 - 7:53pm
Archie Leach

Why does my gaydar go off whenever I look at bands from the 1980s?..... and I'm not even gay.

Jun 05 12 - 3:53am
imp

Lost love certainly does make for some good songwriting. I want to throw "No Regrets" by Scott Walker/the Walker Brothers up on here. It's so gorgeous and optimistic!

Jun 05 12 - 2:31pm
Steph

I know a lot of people are probably wondering why Ben Folds Five's "Song for the Dumped" didn't make the list. For my money, I'm scratching my head at the exclusion of "Smoke" (off the same album, BFF's Whatever and Ever Amen). The extended metaphor of tearing apart a book to represent the dissolution of the speaker's relationship is spot on. Come to think of it, that record also contains one of the best love songs in "Kate" (and she speaks! and she breathes!)

Jun 06 12 - 12:28pm
Ben

Though the top 25 is fairly solid, I don't know how anyone could put Justin Timberlake above Jeff Buckley's 'Lover' on a list of any kind.

Jun 11 12 - 1:34am
heavyshield

led zepplin - babe, I'm gonna leave you

Jun 14 12 - 6:43pm
Graham Clark

Not a bad list.

That said:

1. Nina Simone's "Ne me quitte pas" over Jacques Brel's? Madness.

2. Nine Bob Dylan break up songs better than "Don't Think Twice It's Alright":

"Boots of Spanish Leather"
"I Don't Believe You"
"Farewell Angelina"
"Mama You've Been On My Mind"
"It's All Over Now Baby Blue"
"Positively 4th Street"
"Simple Twist Of Fate"
"You're Gonna Make Me Lonesome When You Go"
"Love Sick"

Jun 19 12 - 11:14pm
FALCOR12

Eminem - space bound = missing her.
Eminem - love the way you lie = love hate relationships.
Eminem - Kim = obsessed, if I can't have her, no one can.
In that order.

Jun 21 12 - 6:27pm
pfieffur

Dumptruck "Island"

Jun 22 12 - 5:53pm
KRibbons

This is a strange list. And definitely not the greatest breakup songs of all time. It seems pretty partial to a specific style of music and branches out only occasionally. To have a list like this and not include a SINGLE Frank Sinatra or Barbra Streisand song is crazy. Also "Accidental Babies" OR "Rootless Tree" by Damien Rice? Or "Leave" by Glen Hansard? Most emotionally powerful break up songs ever.
My personal favorite will forever be "A Song About Me and My Boy" by Swedish singer Miss Li.

Jun 23 12 - 10:16pm
mimi

what about "Breaking up is hard to do" by Neil Sedaka? mimislifelessons.blogspot.com

Jun 26 12 - 3:57pm
JohaN

leaving aside the obscure stuff (like ANY song by Trembling Blue Stars, pretty much)... surely "Walk Away Renee", either the original by Left Banke, or the Four Tops version deserves some placing on this list?

Jul 01 12 - 10:02am
mark

Nick Cave: Far From Me. Brilliant from beginning to end, but containing the final killer stanza:

You told me you'd stick by me
Through the thick and through the thin
Those were your very words
My fair-weather friend
You were my brave-hearted lover
Who at the first taste of trouble went running back to mother
So far from me
Suspended in your bleak and fishless sea
Far from me

Jul 02 12 - 4:10pm
anon

kate nash "nicest thing". heartbreaking

Jul 06 12 - 12:48pm
ChrisD

Although an artist who is otherwise not widely known in the mainstream music industry, Ben Folds should, at the very least, have one spot somewhere on this list. Several of his tracks illustrate the hardship of breakups and life after, including: Mess, Evaporated, Landed, Fair, and Time (to name a few). His unparalleled story telling paired with his musical mastery should have earned him a spot on this list. I feel this list should thus be renamed "The 50 Greatest MAINSTREAM Breakup Songs of All Time"

Sep 15 12 - 5:07am
Tucker

Seconded.

Jul 08 12 - 3:30am
n5m3

well acording to me i think the number one song would have to be love is a loosing game by--Amy winehouse *no hate*

Jul 23 12 - 6:02pm
Anon

And Payphone guys?

Jul 25 12 - 1:31am
Chuq

I think this acoustic is a pretty sweet break up song lol

http://www.youtube.com/watch?v=zYRX-W1WvvM&feature=autoplay&list=ULuuEqp...

Aug 19 12 - 10:18am
Mychelle

what about "Every Rose Has Its Thorn"?

Aug 26 12 - 10:06pm
Me

"Forget Her" by Jeff Buckley should be on the list. Just sayin'.

Sep 02 12 - 6:03pm
BRIAN D

Where's ANY song from Back to Black? Every one of them is a perfect contender, especially "You Know I'm No Good," Back to Black," and "Love is a Losing Game" ...

Sep 05 12 - 6:28pm
Cristina

Back in Black by (the late)Amy Winehouse

Sep 14 12 - 5:51pm
Raymond

WHERE THE F*CK IS PHIL COLLINS AGAINST THE ODDS?!

Sep 15 12 - 5:10am
Tucker

Right?! Or 'I Wish It Would Rain Down'.