25. The Shangri-Las, "He Cried"
I'm pretty sure this is the only song on the list told from the point of view of the dumper, and she's pretty coldly descriptive. But, man, read between the lines and think about that poor guy. "I knew that our romance was over and done/But for him it had just begun." Shit, bro.
24. Girls, "Laura"
Christopher Owens's recently released solo album is an instant-classic break-up album, but I wanted to sit with it before I put it on a list like this. So I'll settle instead for this song by his former band, which is touchingly conciliatory in tone. You might not be there yet, but god willing you'll get there, eh? But seriously, Lysandre is where it's at...
23. The Everly Brothers, "Crying in the Rain"
The Everlys recorded quite a few great break-up songs, particularly once they went to Warner ("Walk Right Back" is exceptional), but this one, about keeping your pride, is the best of the lot.
22. Harry James, "You Made Me Love You"
There's something cathartic in accusation, in shifting the blame, which this standard brilliantly captures: "You made me love you! I didn't want to do it!" WHY DID YOU DO THAT IF YOU WERE JUST GOING TO LEAVE ME?
21. Bob Dylan, "One of Us Must Know"
I was going to put "I Threw It All Away" from Nashville Skyline on here, but a friend suggested this song instead, and I said, "oh yeah, holy shit, I was going through a tough breakup once and this song came on and I had an honest-to-god fucking epiphany thanks to it," and he said the same thing had happened to him! So, I mean, this is obviously an important, powerful song.
20. Smokey Robinson, "The Tracks of My Tears"
Like "Crying in the Rain," this is another song about maintaining your pride by not crying in front of the person who dumped you. Though I would recommend you be honest about your feelings with the people you care about, even if they've hurt you.
19. The Beach Boys, "The Old Master Painter"
Sometimes something so simple can be so effective. Here, it's changing the lyrics of "You Are My Sunshine" to the past tense, combining with Brian Wilson's new music to make something hauntingly sad.
18. Magnetic Fields, "Meaningless"
This delivers the perfect dose of cynicism and despair in Stephin Merritt's typically droll and witty lyrics. "Meaningless, like when two fireflies fluoresce, just like everything I guess, less less yes, it was totally meaningless." Amen.
17. Alabama Shakes, "Heartbreaker"
What I like so much about this song, besides Brittany Howard's howlingly wounded delivery, is the implication of the lyrics. "How was I supposed to know you was a heartbreaker?," she sings, as though being a heartbreaker is who this guy is, and breaking a heart not just something he once did.
16. Fiona Apple, "Oh Well"
I imagined some of you giving me shit for putting Fiona Apple on here, but you know what? Fuck it—she's awesome! Her draggy, jerky piano part here creates the perfect landscape here for "oh, Fiona" lyrics like "A voice once stentorian is now again meek and muffled!"
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."
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.
10. The Clash, "Train in Vain"
Mick Jones captures the desperation of the brokenhearted here: "I need new clothes, I need somewhere to say/But without all of these things I can do/But without your love, I won't make it through." There's also an accusatory chorus, which always feels good.
9. Bob Marley, "She's Gone"
This deep-album cut's simple lyrics are given power by Marley's performance, especially the build ups of the title phrase from mutter to shout, to the point that I walk around my apartment hollering "oh mockingbird have you ever heard words that I never heard?" with great feeling even though I don't know what he's talking about.
8. Dillard and Clark, "Why Not Your Baby?"
The best break-up songs communicate plainly and effectively something simple and universal. "Why don't you call me your baby anymore?" is one such example, from the chorus of this catchy, lovely song.
7. Elliott Smith, "Everything Reminds Me of Her"
I rediscovered Figure 8 not too long ago, and recognized its value not only as Smith's best album but as a great break-up album. "I Better Be Quiet Now" might be my favorite track on the record ("I got a long way to go/Getting further away"—oof), but the title of this song so neatly expresses such a fundamental and devastating part of the break-up experience that I couldn't not put it on here.
6. Harry Nilsson, "I Wonder Who's Kissing Her Now"
If you don't know A Little Touch of Schmilsson in the Night, Nilsson's Gordon Jenkins-arranged standards album, you're missing out on one of the best records ever cut. You're also missing out on a great break-up record, featuring songs like "What'll I Do?" and "Nevertheless." (The special edition also features "I'm Always Chasing Rainbows," which is killer.) But no song is more moving than this 1909 standard, so simple, sad and direct: "I wonder who's buying the wine/For lips that I used to call mine."
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