CRUEL INTENTIONS (1999)
ROGER KUMBLE
Plot
A preppie version of "Dangerous Liaisons", with the decadence, deception and double-dealings taking place in upmarket Manhattan. High school's breaking up for summer and revoltingly rich romeo Sebastian Valmont (Ryan Phillippe) is challenged by spiteful step-sister Kathryn (Sarah Michelle Gellar), who's been dumped by her society boyfriend, to seduce the ridiculously naive Cecile, who's replaced her. Sebastian, however, is far more interested in copping off with the new headmaster's daughter, Annette (Reese Witherspoon), who's taken a public vow of celibacy, and so the pair strike a bet. If Sebastian fails in his bid to deflower both his victims, Kathryn gets his prized vintage Jag. If he succeeds, he gets Kathryn's body for one night of illicit lust. A lightweight but lavish-looking update, with plenty of eye candy.