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She's All That

If you don't remember She's All That, you literally must not have been alive in 1999. Popular dude Zack Siler (Freddie Prinze Jr.) bets his evil friend (Paul Walker) he can turn the school's most unpopular girl (Rachael Leigh Cook) into the prom queen. Casting highlights include Matthew Lillard, Jodi Lyn O'Keefe, Anna Paquin, and, best of all, Usher and Lil' Kim.

Source: Miramax

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