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.