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Not Another Teen Movie (#1)(#2)(#3)(#4)(#5)(#6)(#7)(#8)

IMDb: At John Hughes High School, the students are the same as just about every other teenager in a teen movie. The popular jock, Jake (Chris Evans), takes a bet from Austin, the cocky blonde guy (Eric Christian Olsen), that he can transform Janey, the pretty ugly girl (Chyler Leigh), into the prom queen before the prom. But two people are trying to stop Jake from succeeding: his evil sister, Catherine, the cruelest girl in school (Mia Kirshner), and Priscilla, the bitchy cheerleader (Jaime Pressly). And all of their friends are the same as any other teen movie: Areola, the naked foreign exchange student (Cerina Vincent), Les, the beautiful weirdo (Riley Smith), Malik, the token black guy (Deon Richmond), the desperate virgins (Cody McMains, Samm Levine, and Sam Huntington), Amanda Becker, the perfect girl (Lacey Chabert), Ricky, Janey's obsessed best friend (Eric Jungmann), and Sadie, the VERY old undercover reporter (Beverly Polcyn).