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In the game of seduction, there is only one rule: Never fall in love.
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.

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

Cruel Intentions is a 1999 American teen romantic drama film written and directed by Roger Kumble and starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of the novel Les Liaisons dangereuses, written by Pierre Choderlos de Laclos in 1782, but set among wealthy teenagers attending high school in New York City instead of 18th-century France. The film started as a smaller budget independent film, but was picked up by Columbia Pictures and released on March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Philippe, and Witherspoon were praised. Cruel Intentions was a box office success, earning $76 million and spawning two further films, both direct-to-video.
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