The 25 Greatest Breakup Songs of the 1960s

It ain't no use to sit and wonder why, babe.

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, which is a sneaky way to let us put The Beatles on here twice. Come back next week for the best breakup songs of the '70s, 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 our '60s list. — The Nerve Editors

25. The Box Tops, "Cry Like a Baby"

"Cry Like a Baby" is a song about being infantilized by heartbreak, sung by a guy who wasn't much more than an infant himself. Still, though Alex Chilton was only eighteen when this song came out, he sounds like he's been through sixty years of pain. (Weirdly, he actually started sounding younger as he aged.) — Peter Smith


24. Tammy Wynette, "I Don't Wanna Play House"

It's easy to have a snide response to country's tear-in-my-beer weepers. But for all its maudlin details, "I Don't Wanna Play House" is a more mature view of a break-up than many of the other songs on our list, if only because it looks at the impact of a broken relationship on someone other than yourself.— Alex Heigl


23. Led Zeppelin, "Babe, I'm Gonna Leave You"

It's hard to believe this started out as a folk song. But in the hands of a group of men to whom subtlety was a dirty word, "Babe, I'm Gonna Leave You" turned into a bombastic reflection on just... fuckin'... needing to ramble, or something. Robert Plant's stepped-on-cat howls and that epic, stomping riff at 2:26 (recycled so effectively by everyone from Chicago to George Harrison to Green Day) are about as heavy as heartbreak can possibly be. — A.H.


22. Love, "Alone Again Or"

With its Latin-inflected arrangement, this song gives a sense of tragic grandeur to the prospect of waiting all night for a girl who'll never show up. Normally, that's a really shitty way to spend the evening, but throw on this record and the thought will seem almost stirring. — P.S.


21. Patsy Cline, "I Fall to Pieces" 

"I Fall to Pieces" is the best possible musical expression of the dismay one feels after hearing that hoary old entreaty to "still be friends." The vocal melody's odd leaps and the sprightly bounce of the backing track belie the deep (and universally relatable) sentiment of the song: "You did this to me, and you want to be friends?" — A.H.


20. Elvis Presley, "Return to Sender"

Our generation doesn't value letters, and by extension, the crushing letdown of having one returned, seriously enough. The terrible finality of Elvis' determination in this song's brief bridge ("This time I'm gonna take it myself and put it right in her hand/ And if it comes back the very next day then I'll understand the writing on it") makes the last chorus that much sadder: if this last-ditch effort fails, there really will be "no such person." Not for him, anyway. — A.H.


19. Ray Charles, "Bye Bye Love"

Never has heartache felt so damn buoyant. "Bye Bye Love" bounces along joyously as Charles recites lyrics that wouldn't have sounded out of place in a Dashboard Confessional song forty years later ("Bye bye love, bye bye sweet caress / hello emptiness, I feel like I could die"). He makes heartache seem somehow freeing — just try putting this song on and staying in a bad mood. — A.H.


18. Otis Redding, "I've Been Loving You Too Long (To Stop Now)"

This is one of the best songs ever about the slow heat-death of a relationship. The worst breakup is the one you see coming from a mile away but remain powerless to stop, and Redding nails that ache — the way his voice sweeps up to the high note on "You are tired" is a thing of painful beauty. — A.H.


Commentarium (42 Comments)

Mar 26 12 - 1:49am

So glad to see my favorite breakup song top this list.
For the Stones, I prefer Angie. Yes, I know Mick Jagger's whistpering in the middle is kind of silly, but as a breakup song, it's just fantastic nonetheless.

Mar 26 12 - 8:32am

Angie was released in '73, so perhaps you'll see it next time :D

Mar 26 12 - 9:14pm

Had that thought after I posted. Thanks for the reminder. The late 60s and the early 70s run together in my head. I expect it should make the 70s list. :)

Mar 26 12 - 2:57am

I can't believe Michael Jackson's older brothers let him join their group. He was so much the obvious star.

Mar 26 12 - 5:00am

no Shangri-Las...

Mar 26 12 - 11:19am

'In Dreams' should be disqualified based solely on the Blue Velvet connection. I don't think of a break-up, I think of an overly made-up Cylon serenading Dennis Hopper.

Mar 26 12 - 1:08pm
Alex Heigl

That did come up. But do you disavow "Time is On My Side" for being in a disappointing mid-90s Denzel vehicle? (That would be "Fallen" for those of you keeping track at home.)

Mar 26 12 - 11:25am
Steve Burns

No argument with #1.

Mar 26 12 - 12:10pm

The whole time I was reading this list I'm thinking, "Where the hell is Dylan?" Well okay then, he's number one. But there are so many other songs - especially on "Blood on the Tracks". "Idiot Wind" anyone? Hello? "Tangled Up in Blue"?

But he's been writing killer breakup songs for over 50 years. "It Ain't Me, Babe", "Just Like a Woman", "Visions of Johanna".

I'm just sayin'...

Mar 26 12 - 1:07pm
Alex Heigl

Blood on the Tracks is '70s and will almost certainly be making an appearance next week. As for Leonard, "So Long Marianne" was in the running -- that song was literally #26. Damn our brevity!

Mar 26 12 - 4:29pm
Sean Morrow


Mar 26 12 - 12:43pm

One more note. Nothing from the dean of romantic despair - Leonard Cohen? "So Long, Marianne" is a worthy choice. And, you know, a gazillion more.

Mar 26 12 - 1:28pm
Kate G

I disagree with the reading of Je ne regrette rien. It's not forlorn, it's more empowered. She's lighting a fire with her memories, she doesn't give a damn about the past. And the last line says, "My life, my joy, today, it starts with you." At least to me, it sounds more like a declaration of new love and completely abandoning any past relationships or hardships in order to put herself totally into this new life.

On a different note, I love that song, and whenever I have to do chores I blast Edith Piaf to make them more tolerable.

Mar 27 12 - 2:11pm

Yes. Just because the song is in French doesn't mean you get to just go with your gut feel as to what you *think* the song is about.
She is clearly saying that she doesn't regret anything that has brought her to this point because she is starting a new love. Not a breakup song at all.

Mar 27 12 - 11:33pm

Arguably, it's still a breakup song. It's just a breakup song about not regretting a breakup. Not all breakups are ones you feel bad about, and I'm glad to see that sentiment reflected on this list.

Mar 26 12 - 1:53pm

No "It Ain't Me Babe"?

You say you're looking for someone
Never weak, but always strong
To protect you and defend you
Whether you are right or wrong
Someone to open each and every door
But it ain't me babe
No, no, no, it ain't me babe
It ain't me you're looking for, babe

Mar 26 12 - 11:46pm

Great list! I absolutely love "In Dreams" and do not dispute its inclusion on the list. However "It's Over" takes it as the depths of despair during a breakup for me in terms of Orbison songs. I know there are many to choose from and I'm sure the debate lead deep into the night at the Nerve offices.

Mar 27 12 - 1:18am
oren hatch

driveway to driveway by superchunk.

"my hand on your heart has been replaced, and i thought it was you that i had chased..."


Mar 27 12 - 10:29am
Alex Heigl

From 1992? Check back and see if it makes it onto the '90s list. But that was an angsty decade -- stiff competition.

Mar 27 12 - 3:49am

What about "Break it to Me Gently" recorded by Brenda Lee? Made it to #4 on the charts in 1962. Awesome song!

Mar 27 12 - 6:30am

What? How could you leave out "You're gonna miss me" by 13th Floor Elevators!

Mar 27 12 - 10:39am

I refuse to accept the legitimacy of any "Greatest Breakup Songs of the 1960s" that doesn't include the Stone Poneys "Different Drum".

Mar 27 12 - 11:10am
Alex Heigl

Linda Ronstadt is forever banned from Nerve.

She knows what she did.

Mar 27 12 - 10:45am

Thanks for including a couple of country songs. Those often get overlooked in lists like this. Personally, I'd have included "She Even Woke Me Up (To Say Goodbye)" as well.

Mar 27 12 - 11:12am

I would have gone for the Everly Brothers version over Ray Charles for "Bye Bye Love" --not that it's anything less than genius from Ray, but the Everlys had the hit.

Mar 27 12 - 11:28am
Alex Heigl

I actually really wanted "Drown in My Own Tears," but it's from the wrong decade. I just love the juxtaposition of Charles' "Bye Bye Love" -- those borderline suicidal lyrics and that infectious performance.

Mar 27 12 - 2:29pm

Hey, if you're already thinking about the 1970s, you sure better include Roxy Music. Right now I'd lean toward "Just Like You" off the "Siren" album but "A Song For Europe" is also a possibility and heck, there are about 15 others.

Mar 27 12 - 4:28pm

What about The Moody Blues' "Go Now"?? And Roy Orbison's "Crying"???
Geez..not missing a few good 1960s breakup songs...

Mar 30 12 - 5:42pm

I was thinking along the same lines, Jess, but Bessie Banks' original recording of "Go Now." It wrings the neck of the Moody Blues' version like you wouldn't believe.

Mar 27 12 - 9:24pm
old dude

I'd include "You're Gonna Miss Me (When I'm Gone)" by 13th Floor Elevators and "Remember" (aka "Walking in the Sand") by the Shangri Las.

Mar 27 12 - 10:35pm
Uncle Phil

Just for that comment regarding Linda Ronstadt, I will be playing her "Greatest Hits" much longer now than I expected! Both volumes!

Mar 28 12 - 4:01pm

first off... that's not dylan singing on your clip... it's some douchebag. Secondly to not have 'It Makes No Difference' on your list immediately invalidates it

Mar 28 12 - 5:38pm
Alex Heigl

Well, we fixed the Dylan song. But I'd like to point out that "It Makes No Difference" is from 1975. So, um, pot. Kettle. Black. And such.

Mar 30 12 - 4:55pm

What about that ultimate Dylan kiss off song "Like a Rolling Stone"?

Mar 30 12 - 8:03pm

Couple of months too old to be on this list I think, but I needed to get this off my chest. Jacques Brel's original rendition of 'Ne Me Quitte Pas' is the most beautiful, gut-wrenching piece of music ever created. Nina Simone is okay though.

Mar 31 12 - 1:24pm

For future list consideration: "Two Outta Three Ain't Bad" by Meat Loaf and "Things Change" by Dwight Yoakam. "Things Change" is just so matter-of-fact it's incredibly sad.

"She said, 'I still love you so.' I said, 'I don't care to know.'
She said, 'you once cried my name.' I said, 'well baby, things change.'"

Apr 02 12 - 2:06pm

"i want to be free" by the monkees. my 5th grade boyfriend sent it to me on the radio. what a way to get dumped!! i'll never forget.

Apr 03 12 - 12:32am

Bobby Vinton's "After Loving You". Although I did the breaking up, I cried my eyes out listening to that song!

Apr 03 12 - 1:16pm

You missed Harry Nilsson's "Without Her" as performed by BS&T on their first album. I see you did get Harry's "Without You" in the 70s list, in a justifiably high ranked position too, so well done on that one. One gets the impression Harry had a lot of bad luck with the ladies.

Apr 19 12 - 2:37pm

"Without her " is perfect for crying in your beer music, but when you finally get pissed you need Harry's "You're breakin my heart" as in;
"You're breakin my heart, you're tearin it apart, so fuck you."
Finish beer, order more, feel better.

Apr 19 12 - 2:42pm

Have you kids ever heard "You've got your troubles, I've got mine" by the Fortunes? Great stuff if you like vindictive.

Jun 09 12 - 1:25pm

You can put this in any decade you want. 60s, 2000s or any remake in between.
"What becomes of the broken hearted"
The original is great
the Joan Osborne version from the Funk Brothers Motown documentary is fantastic.
Makes me cry.
In fact, this may not belong in the break up song category.
It is in a class including only itself