The 25 Best Break-Up Songs
15. Paul Simon, “Graceland”
Is this really a break-up song? Probably not, but there’s that one verse that, man, just blows me apart: “She said losing love is like a window in your heart. Everyone can see you’re blown apart.”
Frank Sinatra sings It’s Alright With Me from Caio Fontoura on Vimeo.
14. Frank Sinatra, “It’s Alright With Me”
Sinatra never sounded as sad as he did singing this Cole Porter song—his voice is so soft, like they did the take at 4am after he’d been crying all night.
13. Annette Hanshaw, “Lover Come Back to Me”
This has one of my favorite break-up lines: “Every road I walk along I’ve walked along with you/No wonder I am lonely.” It seems particularly apropos for urban romances: the walks home from the bar and the subway station and the grocery store and oh god
12. Al Green, “I’m So Tired of Being Alone”
This is just one of those refrains you just learn to absorb into your heart so that you carry it around with you always, like Franny Glass and her Jesus Prayer.
11. Supremes, “Baby Love”
Pretty much every Supremes song is a great break-up song, but this one edges out the rest (even if it’s just a knock-off of the group’s “Where Did Our Love Go?”): Diana Ross rarely sounds so sad and sexy as she does here, and though the lyrics are so simple they’re kinda stupid (“Been missin’ ya/Miss kissin’ ya”), they’re also somehow devastating at the same time.