Cruel Intentions

1999 · Directed by Roger Kumble

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Cast: Reese Witherspoon, Ryan Phillippe, Tara Reid, Selma Blair, Christine Baranski, Sarah Michelle Gellar, Louise Fletcher, Joshua Jackson, Eric Mabius, Sean Patrick Thomas

Rating: 6.782/10 from 2,730 votes