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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.