Cruel Intentions (1999)

Description

Kathryn Merteuil (Sarah Michelle Gellar - Scooby Doo, The Grudge) and Sebastian Valmont (Ryan Phillippe - Gosford Park) are two gorgeous, filthy rich, manipulative stepsiblings from Manhattan's upper east side. Bored of the girls he has so easily seduced in the past, Sebastian has set his sights on the ultimate challenge - the beautiful, virginal, headmasters' daughter Annette Hargrove (Reese Witherspoon - Legally Blonde, Vanity Fair). Kathryn sees the perfect opportunity for a wager. If Sebastian fails to lure Annette into his bed, he will have to surrender his priceless vintage Jaguar; if he succeeds, he will win the most tempting prize of all - Kathryn. Sparks fly in this wickedly sexy tale of seduction as Kathryn and Sebastian play a dangerous game of sex and betrayal...