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Just Jared's Favorite 90s Teen Movies!

Cruel Intentions

Year: 1999

Cast: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair, Joshua Jackson, Eric Mabius, Sean Patrick Thomas, Swoosie Kurtz, Christine Baranski

Synopsis: Kathryn makes a diabolical bet that her step-brother, Sebastian, won’t be able to bed Annette (a virgin, who wants to wait until love). If he loses, Kathryn gets his Jaguar, if he wins, he gets Kathryn.

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