Cruel Intentions (1999)


Sarah Michelle Gellar   Kathryn Merteuil
Ryan Phillippe          Sebastian 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
Charlie O Connell       Court Reynolds

Directed by:            Roger Kumble
Produced by:            Michael Fottrell, William Tyrer, Bruce Mellon


A thoroughly modern update of Dangerous Liaisons and Valmont, here we have Kathryn (Sarah Michelle Gellar) 
making a bet with her step-brother, Sebastian (Ryan Phillippe) that he will not be able to break down the 
resolve of a virgin (Reese Witherspoon) who plans on remaining that way until marriage. If Sebastian wins, 
he gets to have the one girl he has never been able to have -- his step-sister. If his step-sister wins 
the bet, she gets the keys to his classic Jaguar.

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A tale of betrayal centering on two wealthy, manipulative teenage stepsiblings from Manhattan's uppercrust. 
It's summer break, and Kathryn has been dumped by her beau, Court Reynolds, for the innocent Cecile. 
Desperate to get even, Kathryn challenges Sebastian to ruin Cecile by deflowering her--thus humiliating 
Court by delivering Cecile to him as damaged goods. Sebastian has pretty much 'had' all of the girls in 
New York City up to this point, and he's gotten a bit bored of it all. Though this is too easy a conquest 
for him, he obliges. He sets his sights on a higher challenge--the headmaster's daughter, Annette, who 
recently wrote an article in 'Seventeen' Magazine about how she intends to stay pure until she marries 
her boyfriend. Sebastian bets Kathryn that he can seduce the chaste and pristine Annette. Kathryn believes 
it impossible, and agrees to the wager--and if Sebastian succeeds, Kathryn must give him a night of 
unbridled pleasure, something he's wanted since their parents got married.