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.
Acting
Gellar's ice-queen delivery is permanently etched in pop culture.
Writing
Dialogue so vicious it circles back to poetry.
Costume
That cross necklace launched a thousand Catholic schoolgirl fantasies.
Director
Roger Kumble
Sarah Michelle Gellar
Kathryn Merteuil
Ryan Phillippe
Sébastian Valmont
Reese Witherspoon
Annette Hargrove
Selma Blair
Cecile Caldwell
Louise Fletcher
Helen Rosemond
Joshua Jackson
Blaine Tuttle
Eric Mabius
Greg McConnell
Sean Patrick Thomas
Ronald Clifford
Swoosie Kurtz
Dr. Greenbaum
Christine Baranski
Bunny Caldwell
Alaina Reed Hall
Nurse
Deborah Offner
Mrs. Michalak
Tara Reid
Marci Greenbaum
Herta Ware
Mrs. Sugarman
Hiep Thi Le
Mai-Lee
Trivia, insights & behind the scenes
This film essentially created the 'hot rich teens being evil' template that Elite and Gossip Girl still mine today.
The famous kiss was added after Gellar and Blair realized their characters' tension—originally it was just a hug. Director Roger Kumble shot it in one take.
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