Cruel Intentions [796] Released: 1999-03-05 Revenue: $76,347,426 Budget: $10,500,000 Profit: $65,847,426 Runtime: 98 mins Popularity: 7.0479 Vote Average: 6.807 Vote Count: 3,362 Overview: 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 [19] Ryan PhillippeSébastian Valmo Sarah Michelle GellarKathryn Merteuil Reese WitherspoonAnnette Hargrove Selma BlairCecile Caldwell Louise FletcherHelen Rosemond Joshua JacksonBlaine Tuttle Eric MabiusGreg McConnell Sean Patrick ThomasRonald Clifford Alaina Reed HallNurse Hiep Thi LeMai-Lee Deborah OffnerMrs. Michalak Tara ReidMarci Greenbaum Drew SnyderHeadmaster Hargr Herta WareMrs. Sugarman Swoosie KurtzDr. Greenbaum Christine BaranskiBunny Caldwell Charlie O'ConnellCourt Reynolds Fred NorrisMeter Maid Ginger WilliamsClorissa Hompage: https://www.CruelIntentions.com Trailers Official Trailer