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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).

Van Wilder is a guy who has been at his college for seven years. He spends most of his time throwing parties and “fund raisers”. When his father decides that it’s time for tough love, he doesn’t pay his tuition. So Van becomes a professional party thrower. At the same time, Gwen who writes for the college paper, is tasked with doing a story on him, but Van is too busy partying to do that. So she writes it using info from people who talk about him and writes an unflattering piece, which doesn’t make him happy. He then dares her to see if she can get the true story but is more interested in trying to score with her, which is not easy because she has a boyfriend, who is a snob, and who is not too happy with the amount time she is spending with him. So he tries to get rid of him.