Cruel Intentions

• Sarah Michelle Gellar as Kathryn Merteuil
• Ryan Phillippe as Sebastian Valmont
• Reese Witherspoon as Anette Hargrove

Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn.
Year: 1999