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15. Lauryn Hill, "Ex-Factor" (1998)
Preternaturally gifted as a rapper, producer, and singer, Lauryn Hill really could do it all. The Miseducation of Lauryn Hill touched on virtually every kind of pain there is, from racism to disenfranchisement to plain-and-simple heartbreak. The last reached its exquisite peak with "Ex-Factor," which Wyclef Jean has since revealed is about him. "Cry for me, cry for me, you said you'd die for me," an overdubbed choir of Hills sings accusingly at the song's climax — it's hard not to feel like you're in the crosshairs during that line. — A.H.
14. Smashing Pumpkins, "Perfect" (1998)
Our other Smashing Pumpkins nomination was more characteristic: "Soma," a dreamy, seven-minute psych-rock epic. "Perfect" falls at the opposite end of the spectrum. It's a low-key, gentle, honestly sweet farewell, wistfully anticipating a future where two lovers have become two strangers passing in the street. Always a weird experience. — P.S.
13. Fiona Apple, "Sleep to Dream" (1996)
Fiona Apple is the voice of smart women everywhere who are consistently underwhelmed by their men. "Sleep to Dream" is the best of her many, many breakup songs; they're all great, but this one is damn empowering. You can't hear it without feeling at least a little more badass, even if you aren't getting over someone. The reprise says it all: "So don't forget what I told you / Don't come around, I got my own hell to raise." Preach, Fiona, preach. — R.K.
12. Stone Temple Pilots, "Interstate Love Song" (1994)
That monster riff might not immediately scream "breakup" — to me, it screams "bitchin'" — but with lyrics like "You lied, goodbye" prefacing "Leavin' on a southern train," it's not hard to assume it's about some kind of breakup. Or heroin. Probably both, actually. Either way, it's a great song to play when triumphantly driving down the road, one arm high in the air. — A.H.
11. Ben Folds Five, "Song for the Dumped" (1997)
In one of the angriest breakup songs of the '90s, Ben Folds makes damn sure that his ex gives him back all the souvenirs she collected during their relationship. Whatever she did that warrants being called a "bitch" over and over must've been bad. Let's just hope he finally got his black t-shirt back. — J.G.