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5. Wilco, "I Am Trying to Break Your Heart" (2002)
Jeff Tweedy often seems to be trying to obscure his emotional songwriting with avant-garde touches like weird ambient sounds, deliberately "wrong-sounding" notes, and obtuse lyrics. But none of those elements can stop "I Am Trying to Break Your Heart" from succeeding in its titular aims. — A.H.
4. 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.
3. Justin Timberlake, "Cry Me A River" (2002)
Who ever would've thought that the dopey fresh-faced bleach-blonde kid from 'NSYNC would grow up to have this much soul? If JT wants me to cry, damn it, I'm cryin'. — J.G.
2. Amy Winehouse, "Tears Dry On Their Own"
The juxtaposition of the music from Marvin Gaye and Tammi Terrell's classic "Ain't No Mountain High Enough" and Winehouse's self-penned lyrics and melody is the first thing you're likely to notice about this song. But last year's Lioness: Hidden Treasures revealed the original version of "Tears," and shockingly, it didn't matter that much — Winehouse's desperate, lonely vocal was just as evocative and touching as ever, proving that no matter how many people accused her of slavish pastiche, Winehouse's voice was always her own. — A.H.
1. Outkast, "Ms. Jackson"
This is probably the only breakup song ever addressed to the singer's mother-in-law, but the gambit pays off. By directing his imploring lines to Erykah Badu's mom instead of Badu herself, Andre 3000 makes an implicit statement about how the idealism of young love ("that crib with the Goodyear swing") gives way to the complexities of adulthood: private schools, day care, lawyers. Mothers-in-law. It's rueful, but it's loving too. — P.S.
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