Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of the 18th-century French epistolary novel Les Liaisons dangereuses by Laclos and is set among wealthy teenagers living in modern New York City. The film started as an independent film with a small budget, and was later picked up by Columbia Pictures. It was released on March 5, 1999 and was followed by two direct-to-video films: a prequel, Cruel Intentions 2, and a sequel, Cruel Intentions 3. The wealthy and popular Kathryn Merteuil (Gellar) takes the sheltered and naïve Cecile Caldwell (Blair) under her wing, promising to turn Cecile into a model student. Kathryn's real intention, however, is to take revenge on her ex-lover, who dumped her. Kathryn asks her step-brother, Sebastian Valmont (Phillippe) to seduce Cecile; he refuses. He is planning to seduce dedicated virgin Annette Hargrove (Witherspoon). Doubting Sebastian's...