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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.
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.
After his precocious behavior has gotten him bounced out of one more in a string of exclusive private schools, 16-year old Sebastian Valmont has arrived in New York City to live with his father and stepmother. The cunning and handsome Sebastian may have met his match, however in his equally manipulative and beautiful stepsister Kathryn Merteuil.
Meet Cassie, Jason and Patrick, three amoral college students who, through a series of sexual wagers, take malicious pleasure in ruining the lives of their fellow classmates.