This story takes place in a posh Manhattan high rise. Featured are two step-siblings, Catherine and Sebastian (Sarah Michelle Gellar and Ryan Phillipe) who have a penchant for the finer things in life, but also in torturing each other with sexual banter. The fun begins when the headmaster's daughter Annette (Reese Witherspoon) enters the picture. Sebastian and his cunning sister enter a wager to see if he can woo the pristine, Annette. Things go awry once Sebastian unexpectedly falls for the new girl in town. Surrounded by an ensemble cast of Hollywood A-Listers, Cruel Intentions is the dramedy of 1999.