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5. Weezer, "Butterfly" (1996)
Closing out a near-perfect album of guilt and angst, "Butterfly" is a devastating story about the guilt of being unable to commit. Totally exposed, Rivers Cuomo confesses to having hurt someone who didn't deserve it. He tries to figure out why he did it, but in the end, all he has are two plaintive words: "I'm sorry." — P.S.
4. Notorious B.I.G., "Friend of Mine" (1994)
This is an ode to those relationships in which both parties screw everything up royally. Biggie gives us the backstory of himself and his lady, which is rife with lies, infidelity, and smack-talkin'. Sometimes the only direction you can point your finger is at yourself. — J.G.
3. Liz Phair, "Fuck and Run" (1993)
The musical, lyrical, and spiritual opposite of "November Rain," "Fuck and Run" is wistful and blunt. A not-very-passionate relationship is dropping off, and it sounds like it's only the most recent of many. This is the lament of someone who wants something more, but is too paralyzed to reach for it. — P.S.
2. Elliott Smith, "Oh Well, Okay" (1998)
In a discography full of gorgeous, devastating breakup songs, it's hard to pick just one. (Also nominated: "Say Yes," "Waltz #2," "Miss Misery," "Between the Bars," "The Biggest Lie," "Condor Ave.," etc.) But "Oh Well, Okay" might be the best of the bunch, a sigh of resignation wedded to one of the most beautiful melodies poor Elliott Smith ever wrote. — P.S.
1. Sinead O'Connor, "Nothing Compares 2 U" (1990)
In my opinion, this is one of the few covers that blows the original out of the water. (My apologies to all the Prince fans out there.) With devastating honesty, Sinead O'Connor mourns a straying lover, while celebrating the freedom of being alone again. Life's great buffet is hers for the taking, but it's all lost its taste. — J.G.
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