Sarah Michelle Gellar as Kathryn Mertevil

Kathryn is the manipulative teenage stepsister of Sebastian Valmont and is from Manhattan's uppercrust. When she is dumped by her beau, Court Reynolds, for the innocent Cecile, she challenges Sebastian to ruin Cecile by deflowering her and turning her into a tramp-thus humiliating Court by delivering Cecile to him as damaged goods.

Ryan Phillippe as Sebastian Valmont

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. When challenged by his stepsister Kathryn to deflower the naive Cecile, he obliges, though this is too easy a conquest for him. He sets his sights on a greater challenge-the new headmaster's daughter, Annette. Sebastian bets Kathryn that he can seduce the chaste and pristine Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager.

Reese Witherspoon as Annette Hargrove

Annette unwittingly becomes a pawn in Sebastian and Kathryn's deliciously diabolical wager of sexual conquest when she writes an article in 'Seventeen Magazine' about how she intends to stay pure until she marries her boyfriend. However, Sebastian gets more than he bargained for as he attempts to woo Annette into his bed.

Selma Blair as Cecile

Having snagged Kathryn's boyfriend Court Reynolds, Cecile becomes a pawn in a wicked game of seduction and betrayal. She is seduced by Sebastian and then becomes an annoyance to them as her sexual appetite grows and grows. (She's really naive).