Roger Kumble's iconic film returns to the big screen for its 20th anniversary. CRUEL INTENTIONS centers on wealthy teens Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe). The duo agrees upon a deliciously diabolical wager of sexual conquest without consequences. The pawns? The naïve Cecile Caldwell (Selma Blair) and the virginal Annette Hargrove (Reese Witherspoon) ... Kathryn challenges Sebastian to ruin Cecile by deflowering her and turning her into a tramp. He obliges, but sets his sights on a greater challenge—the new headmaster’s daughter, Annette, who recently wrote an article in a magazine about how she intends to stay pure until she marries her boyfriend. Sebastian bets Kathryn that he can seduce the chaste Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled biblical pleasure, something he’s wanted since their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat.