MOVIE · 1999

Cruel Intentions

DramaRomance98 min

At a Manhattan prep-school orbit of money and privilege, Sarah Michelle Gellar’s Kathryn proposes a summer wager to her stepbrother Sebastian (Ryan Phillippe): seduce Annette, the headmaster’s idealistic daughter, before summer ends, and claim the prize Kathryn has been holding over him. What starts as another round in their private game of manipulation soon pulls in classmates, rumors, and carefully managed reputations. Reese Witherspoon’s Annette stands apart from the crowd Sebastian usually targets, which complicates a contest built on status, sex, and control among affluent New York teens.