"Cruel Intentions" is about a foster brother and sister who hold prominent positions at an elite New York City private school. Both of them enjoy manipulating others and playing cruel games. The siblings are Sebastian (Ryan Phillipe) and Katherine (Sarah Michelle Gellar). Katherine makes a bet that Sebastian cannot seduce a new student named Annette (Reese Witherspoon). If Katherine wins the bet, she gets Sebastian's car. If Sebastian wins, he gets Katherine.
Sebastian attempts to win over Annette, but his initial attempts are rebuffed. He eventually realizes that he has fallen for Annette and is genuinely in love with her. This enrages Katherine, who is jealous of the attention Sebastian is lavishing on Annette. Meanwhile, matters are further complicated by Katherine's plan to destroy a naive young woman named Cecile (Selma Blair), who has recently enrolled in Katherine's school. Cecile is dating Katherine's ex-boyfriend. Meanwhile, Cecile falls for her music teacher, Ronald.
The characters, especially Katherine, weave a web of deceit as they try to manipulate and triumph over one another. Sebastian must reconcile his feelings for Annette and his emotions toward Katherine. Sebastian's life is thrown into turmoil after he confesses the bet to Annette. They become estranged, but later take steps toward reconciliation. However, a tragic event changes everyone's lives. By the end of the film, some characters have grown more cynical, while others have been publicly exposed for who they really are.
The movie is an adaption of the French 1782 novel "Dangerous Liasons", which was later made into an American film of the same name in 1988. "Cruel Intentions" changes the setting and involves younger characters. All three versions involve a male and female pair of people who cruelly and coldly manipulate others to serve their own ends. However, in all versions, the male manipulator falls in love with the woman he is supposed to seduce.
"Cruel Intentions" has a soundtrack filled with music that was new and popular when it was released. The soundtrack was released as a CD. Artists featured in the film include Placebo, Fatboy Slim, Counting Crows, and The Verve.
The film was popular with young adult audiences and won several awards, including two MTV Movie awards (Best Female Performance for Sarah Michelle Gellar, Best Kiss), one Teen Choice award (Best Drama Film), and one Blockbuster Entertainment award (Favorite Supporting Actress for Reese Witherspoon). It was followed by two further installments.