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Loser (2000)
From Amazon:
Writer-director Amy Heckerling has a way with teen comedies, from Fast Times at Ridgemont High to Clueless and now Loser. She manages to take the clichés of life in school and spin them into cinematic gold. Part of her secret is that she genuinely seems to respect all of her characters, even the unsavory ones. In Loser, Paul Tannek (Jason Biggs from American Pie) is a farm-town boy who's gotten himself a scholarship to a fancy Manhattan college. He's worried that he's not going to fit in with the sophisticated city crowd. Well, he's right to worry. He doesn't fit in, which his three dorm-mates are...
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