Year			1999
Genre			Dark comedy
Length			1:37
Director			Roger Kumble
Writer			Roger Kumble
Company			Columbia Pictures
Starring			Sarah Michelle Gellar Ryan Phillippe Reese Witherspoon Selma Blair Louise Fletcher Joshua Jackson Show more... Sarah Michelle Gellar Ryan Phillippe Reese Witherspoon Selma Blair Louise Fletcher Joshua Jackson Eric Mabius Sean Patrick Thomas Swoosie Kurtz Christine Baranski Alaina Reed Hall Deborah Offner Tara Reid Herta Ware

Two bickering step-siblings quietly control much of the social lives of the students in an affluent NY prep school. Sebastian sees himself as a kind of Don Juan, who always gets his woman, while Katherine would rather enact revenge on ex-flames and corrupt incoming freshmen. One day, Katherine and Sebastian, driven by a mutual lust for each other and a love of messing with innocent young people's lives, hatch a nefarious plan, and place a kind of bet. Sebastian is to woo and bed the daughter of the new headmaster, and if he is able to accomplish this seemingly impossible task, he can have his way with Gellar - the one woman whom he KNOWS he can not have. If he is unable to seduce the ice queen, however, Katherine gets his classic Porsche.