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20. Bell Biv DeVoe, "Poison" (1990)
Some say this old-school classic plays to a new era of AIDS consciousness — meaning that, like poison, that girl is literally deadly. I tend to think it's just about a toxic kinda woman, but what really matters is that this song stands the test of time. The scratched record and beat are as catchy now as they were then. And most importantly, this track teaches us an important life lesson: never trust a big butt and smile. — R.K.
19. Alice in Chains, "Heaven Beside You" (1995)
Sung by Jerry Cantrell instead of Layne Staley, "Heaven Beside You" concerns the breakup of Cantrell's seven-year relationship, and it sandwiches perfectly between AIC's two primary moods: bleak and really fucking bleak. Largely acoustic, it's slightly less stomping than the rest of Alice in Chains' catalog. But the band's signature elements (CSNY-on-downers harmonies and epic guitar solos) are fully intact, making this the kind of breakup song acceptable to self-loathing metal dudes the world over. — A.H.
18. Mariah Carey, "Heartbreaker" (1999)
Not all breakup songs have to feature sadness and acoustic guitars. Sometimes, getting over a breakup can be as simple as listening to Jay-Z's incessant commands to "Bounce to this" and letting yourself get lost in Mariah Carey's sex-kitten delivery. — A.H.
17. Boyz II Men, "End of the Road" (1992)
Anyone else remember swaying slowly to this at middle-school dances? Even then, I knew this was a classic. It's a quintessential goodbye song — but can't we have just one more dance? — R.K.
16. Green Day, "When I Come Around" (1994)
Green Day's success probably had as much to do with their rhythm section as with anything else (hooks, cuteness). It's not that they're doing anything tricky, but they've got some snap, and that means Green Day just feels good to listen to. In this case, the lyrics to "When I Come Around" don't really say much about the relationship we're strutting out of, but the music sure makes us feel like strutting. — P.S.