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5. Chet Baker, "But Not for Me"
Chet Baker Sings is an essential break-up album; it's so spot-on that it's the only record I've ever had to get up and shut off once because it hurt too much to listen to. There are several break-up classics on here—"I Get Along Without You Very Well," "Just Friends"—but this one is my favorite for its bopping rhythm, easy melody, and resignation.
4. The Beatles, "Anna"
"All of my life I've been searching for a girl to love me like I love you/But every girl I've ever had breaks my heart and leaves me sad/What am I, what am I supposed to do?" The narrator of this song is admirably generous in his willingness to let Anna go, which is why the self-pitying bridge kills it. Lennon's half-screamed delivery doesn't hurt it, either.
3. Hank Williams, "Why Don't You Love Me"
What I love most about Hank Williams is the economy of his songwriting, on a par with the best of the Tin Pan Alley songsmiths (see: "I Wonder Who's Kissing Her Now"). With this song, he boils down the sad confusion at the heart of all break-ups into one simple sentence: Why don't you love me like you used to do?
2. Ben E. King, "Don't Play that Song"
I went through a break-up once where for months I listened to this song multiple times a day. Its appeal is manifold: there's the deeply wounded feeling in King's voice, particularly during the verse that goes "You told me you loved me/You told me you cared..." And there's the way it recognizes that, as comforting as break-up songs can be when you're down, love songs can fuck you up. But my favorite part is the chorus and its repeated insistence that she lied about loving him. Because doesn't "I love you" feel like something you shouldn't be able ever to take back? (Also, Ben E. King has another pretty amazing break-up song: "River of Tears.")
1. Daniel Johnston, "True Love Will Find You in the End"
This is not technically a break-up song, but going through a break-up is hard, and I thought it was important to end this list on an optimistic note. (You might also try listening to "Something's Coming" from West Side Story.) Being single and not wanting to be requires a tremendous act of faith—faith that, as you've met someone before, you'll meet someone again, no matter how impossible it might seem right now. No other song deals with that as well as this song. Well, except maybe "You Can't Hurry Love"? That's your alternate Number One.
Listen to almost all 25 on Spotify. (I had to replace the Beatles with Arthur Alexander, and the Dillard & Clark song is not available in this country.)
Follow Henry Stewart on Twitter @henrycstewart