Cruel Intentions (1999) 15th Anniversary Video Tribute

After cleverly seducing and and ruining the reputation of an unsuspecting classmate, Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) devise their greatest challenge yet. Sebastian must seduce and deflower the headmaster’s beautiful and innocent daughter Annette (Reese Witherspoon). If he looses, he must hand over his most prized possession…if he succeeds, Kathryn will finally give in to his advances and give him what he’s lusted after since their parents got married. But the stakes are higher than any of them realise and this game of cat and mouse is about to take an unexpected turn.