The 25 Greatest Breakup Songs of the 1960s

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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 Hooksexup 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.


17. ? and the Mysterians, "96 Tears"

The organ riff in "96 Tears" is the perfect sonic representation of hormonal heartbreak. It's nagging, it's fiendishly single-minded, you can't ever get it out of your head, and after a while, you start to revel in it. It's a weirdly vengeful song, too, and the lyrics seem largely improvised, all of which speak to its status as an eternal teenage anthem. — A.H.


16. The Beatles, "You've Got To Hide Your Love Away"

John Lennon's breakup songs (like his songs in general) lean towards the existential. Where McCartney's breakup songs tended to focus on the collapse of the relationship itself, Lennon's have a haunted loneliness, as if the whole world has turned on him ("Everywhere, people stare… I can see them laugh at me"). In the Lennon ouevre, the departure of a woman has him questioning the very meaning of his life. See also "I'm a Loser." For me, his greatest is a toss-up between this Dylanesque lament and the eerie, Oedipal "Yes It Is," but it's hard to argue with "You've Got To Hide Your Love Away." — P.S.


15. Nancy Sinatra, "These Boots Are Made For Walkin'"

Encouraged by Lee Hazlewood to sing the song as if she were a sixteen-year-old girl brushing off the advances of a forty-year-old man, Sinatra delivers an empowering "step off" message with a fresh, snappy attitude. — Jeremy Glass


14. The Supremes, "Where Did Our Love Go?"

From the first claps, there's no mistaking this Motown classic. The most sway-able of our picks, "Where Did Our Love Go" was The Supremes' first #1 hit, and deservedly so. The lyrics may be begging and needy, but Diana Ross is such a diva that she can even makes groveling sound badass. This is a great breakup song for the crucial stage of recovery when you're finally ready to sing to your mirror again. — Rachel Krantz


13. The Beach Boys, "Caroline, No"

This musically intricate piece laments a girl who's gone or changed in many ways, an idea not that different from dozens of other songs The Beach Boys had recorded by 1966. But the wandering melody, harpsichord vamp, and rattling sound effects are way, way creepier than "Help Me, Rhonda" ever dreamed of. In its sense of devastating loss, "Caroline, No" almost sounds like it's sung from beyond the grave. — P.S.


12. Roy Orbison, "In Dreams"

Roy Orbison's best songs are operatic, in the best sense of that word. Not just because of his preternaturally athletic voice, but because of their narrative momentum. "In Dreams" is a perfect example: in contrast to the rigid structure of most pop music, the song moves forward, unfolding new sections rather than returning to old ones. When Orbison hits that spine-tingling high note at 2:28, it's like every third-reel climax rolled into one beautiful moment. — A.H.


11. Sam Cooke "Bring It On Home To Me"

Lou Rawls' uncredited backing vocals on this song lend it a commiserating, drinking-buddies-on-a-breakup-bender feel. Cooke and Rawls' voices dip, swell, and surge together, and for all the sadness here, there's a comforting blanket of friendship over the whole song. It's one man with his arm around his friend at the back of the bar, letting him know that he's better off, even if they both know he doesn't really mean it. — A.H.


10. 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.


9. The Rolling Stones, "Ruby Tuesday"

Keith Richards wrote the song about a cherished groupie who got caught up in drinking, drugs, and Jimi Hendrix. For every man whose heart's been broken by a free-spirited artist type, Mick Jagger sings the words we thought but were afraid to say. — J.G.


8. Edith Piaf, "Non, Je Ne Regrette Rien"

"Non, Je Ne Regrette Rien" makes me feel like I should be forlornly walking through a labyrinth of cobbled streets, but be viewing myself from a shaky-cam tracking shot instead of looking out of my eyes. It's in French, but you can still tell that it's about love lost without understanding a word. — Sean Morrow


7. Marvin Gaye, "I Heard It Through the Grapevine"

It was Motown producer Norman Whitfield's idea to have Marvin Gaye sing this song in a register close to the top of his range, so the desperation in his voice is equal parts physical and emotional. But the rest of the song's genius is in the arrangement: sinister electric piano, and pounding tribal drums, a perfect sonic approximation of infidelity-related paranoia. — A.H.


6. Jackson 5, "I Want You Back"

Written about a relationship that ended prematurely, and a lover hastily backpedaling to save it, "I Want You Back" evokes all the mistakes of young lovers in the heat of passion. Regardless of the upbeat tone (and the fact that it was sung by an unusually soulful eleven-year old), this song is a glum reminder that once a relationship is over, something will be lost forever and ever. — J.G.


5. Etta James, "I'd Rather Go Blind"

Over a hypnotic, two-chord vamp, Etta James bares her soul to the point of bloodletting. Her performance starts off relatively low-key and mournful, but by 1:30 ("I was just, I was just, I was just sitting here thinking of your kiss, and your warm embrace"), she's fully in the over-the-top truth of the song: sometimes, it'd be easier to never see again than see someone you love walk away. — A.H.


4. Nina Simone, "Ne Me Quitte Pas"

"Ne Me Quitte Pas" may not be Nina Simone's most well-known performance, but it's definitely one of her best. You don't need to speak French to hear that this song is about begging someone not to leave. A work of exhausted beauty, it's best listened to on repeat accompanied by a bottle of red and a good cry. — R.K.


3. The Beatles, "For No One"

Among Paul McCartney breakup songs, conventional wisdom would give the edge to "Yesterday." But while "Yesterday" is certainly beautiful, with its sweeping strings and simple lyrics, it's more adolescent in its mood than the brutally adult "For No One." Here, McCartney strips out all sentiment in favor of a crisp, hard-headed look at the end of a relationship. It's devastating (and very English). "Yesterday" feels speculative, and McCartney wrote it when he and Jane Asher were still happily together; "For No One," written while they were breaking up, could only have been written by someone who'd been there. — P.S.


2. Smokey Robinson & The Miracles, "The Tracks of My Tears"

Smokey Robinson's gossamer vocals are downright angelic on this song: his voice is so pure, and his pain so impossibly transparent, it's like looking through a beautiful window into a house destroyed by fire. The song's dynamic shifts have a lot to do with its success as well: as the restrained verse accelerates into that skyrocketing chorus, the strings swell, the drums crash, and Smokey's voice wavers above it all, sounding, well, like an angel. — A.H.


1. Bob Dylan, "Don't Think Twice, It's All Right"

Dylan wrote this classic after his girlfriend, Suze Rotolo (who appears on the cover of The Freewheelin' Bob Dylan), told him she was extending her trip to Italy… indefinitely. In a perfect expression of rejection and bitterness, Dylan fills this song with slow burns like "I once loved a woman, a child I'm told/ I give her my heart but she wanted my soul," and of course, that final punch to the stomach, "You could have done better but I don't mind/ You just kinda wasted my precious time/ But don't think twice, it's all right." There's really no better song to listen to when you're hurt but don't want to hurt your pride. — R.K.


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