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29. Justin Timberlake, "Cry Me A River" (2002)
Who ever would've thought that the dopey, fresh-faced bleach-blonde from 'NSYNC would grow up to have this much soul? If JT wants me to cry, damn it, I'm cryin'. — J.G.
28. The Magnetic Fields, "All My Little Words" (1999)
Writing a song is always an act of hope — you'll get your feelings across to someone in a way that matters. You'll create or reaffirm a connection. But after a breakup, all hope is lost, and not even a craftsman as crafty as Stephin Merritt can write anything to fix it. Meaning itself is annihilated, leaving just a pile of forlorn verbiage. I wish I could write songs this good, but then, what difference would it make? — P.S.
27. The Replacements, "Answering Machine" (1984)
The Replacements were notorious for sandwiching heartbreakers like this between ludicrous pisstakes. On Let It Be (even that title!), "Answering Machine" follows closely on the heels of something called "Gary's Got A Boner." No matter; the band's flippant side actually throws the vulnerability of songs like "Answering Machine" into sharper relief. Over an intricate guitar figure, Paul Westerberg yearns to reconnect to a distant girlfriend, but it's clear she's slipping away. — P.S.
26. The Beach Boys, "Caroline, No"
This musically baroque 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.
25. Billy Bragg, "Must I Paint You a Picture" (1988)
"A New England" is a great song, but "Must I Paint You a Picture" is one of the most moving, accurately sketched portraits of a relationship killed by overthinking: "The temptation to take the precious things we have apart to see how they work must be resisted, for they never fit together again." Ouch. — A.H.
24. Paul Simon, "Hearts and Bones" (1983)
Conventional wisdom probably gives the nod to "Graceland" (a great one, no doubt), but we've got to go with "Hearts and Bones," an ambivalent masterpiece about Simon's troubled marriage to Carrie Fisher. These two very different people "return to their natural coasts," but a complex, difficult connection remains: "You take two bodies and you twirl them into one — their hearts and their bones — and they won't come undone." Both tender and sharp, "Hearts and Bones" might be the greatest lyric Simon's ever written. — P.S.
23. Macy Gray, "I Try" (2000)
Though she was unable to capitalize on it, Macy Gray will always be remembered for this perfect pop gem. Her odd vocal affectations (exactly what accent is that, again?) bump up against her band's joyously swinging performance, and by the end of the song, you're less aware of her voice's gravelly timbre than with its exuberance — she's made heartbreak sound like a party. — A.H.
22. 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.
21. The Strokes, "Someday" (2001)
Equal parts regret and boozy barstool philosophy, "Someday" is a broadly focused portrait of a breakup. Though the line "alone we stand, together we fall apart" hints at a relationship dissolved for its own good, the song is as much about letting go of youth as it is about letting go of someone, and Julian Casablancas' disaffected croon obscures some of his most painfully sincere lyrics. — A.H.
20. Rolling Stones, "Angie" (1973)
While most breakup songs come from a place of anger or devastation, in "Angie," Jagger/Richards insist on ending the relationship on a joyful note: "Ain't it good to be alive?" As Mick croons the story of his relationship's painful past, it only serves to emphasize how much better things are going to be now that the relationship is over. It's a breakup song for grownups. — Natasha Ochshorn