48. Weezer, 'Pinkerton'
Rivers Cuomo poured all his self-loathing and loneliness into ten autobiographical songs on Weezer's second album, detailing his awkward love life with agonizing specificity, beginning with "Tired of Sex," where the rock & roll groupie grind has never sounded less appealing. Some real-life girls mentioned on Pinkerton are ones Cuomo had crushes on but didn't date: a lesbian, a girl in one of his classes who rebuffed his invitation to a Green Day concert and an eighteen-year-old in Japan who wrote him a fun letter and with whom he became obsessed, wondering if she thought about him when she masturbated. With all those true confessions, it's no wonder that Cuomo is somewhat embarrassed by Pinkerton now — and that the record became a cornerstone of the next decade's emo movement.