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  1. The naïve Cecile Caldwell (Selma Blair) and the virginal Annette Hargrove (Reese Witherspoon). Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire by making a diabolical wager of sexual conquest without consequences. The pawns?

  2. Sarah Michelle Gellar (I Know What You Did Last Summer, Scream 2, TV's Buffy The Vampire Slayer) and Ryan Phillippe (I Know What You Did Last Summer, 54) sizzle as a pair of unscrupulous siblings in a deliciously sexy tale of seduction, revenge and conquest. After cleverly seducing and ruining the reputation of an unsuspecting classmate (Selma Blair, Can't Hardly Wait, Zoe, Duncan, Jack & Jane ...

  3. Cruel Intentions: Directed by Roger Kumble. With Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair. Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.

  4. Mar 5, 1999 · 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. Slaking a thirst for dangerous games, Kathryn challenges her stepbrother ...

  5. Cruel Intentions. Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term. Rentals include 30 days to start watching this video and 48 hours to finish once started.

  6. Mar 5, 2024 · Cruel Intentions,” the 1999 teen drama which celebrates its 25th anniversary this week, tells the story of spiteful stepsiblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont ...