Cruel Intentions is a 1999 American feature film starring Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon, and Selma Blair. The movie is a drama film based on the 18th century French novel Les Liaisons Dangereuses, but unlike other modern film versions of the novel set in the France of that time (such as Dangerous Liaisons and Valmont), Cruel Intentions is set among the wealthy teenagers of modern-day New York society. The plot is mainly driven by a bet held between the two main characters, and it heavily involves manipulation, seduction, and love in a rich and sophisticated socially elite youth atmosphere. The film started as an independent film with a much smaller budget, it was later picked up by Columbia Pictures. The film was released on March 5, 1999. It was later followed by two direct-to-video films: a prequel, Cruel Intentions 2, and a sequel, Cruel Intentions 3.

Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn Written by Scott Stoecker

Kathryn and Sebastian, two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. The stakes are high when the duo agrees upon a deliciously diabolical wager of sexual conquest without consequences. The pawns? The naive Celcile Caldwell and the virginal Annette Hargrove. Its summer break, and Kathryn has been dumped by her beau, Court Reynolds, for the innocent Cecile. Desperate to get even, Kathryn challenges Sebastian to ruin Celcile by deflowering her and turning her into a tramp-thus humiliating Court by delivering Cecile to him as damaged goods. Sebastian has pretty much 'had' all of the girls in New York City up to this point, and he's gotten a bit bored of it all. Though this is too easy a conquest for him, he obliges. He sets his sights on a greater challenge-the new headmaster's daughter, Annette, who recently wrote an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. Sebastian bets Kathryn that he can seduce the chaste and pristine 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 pleasure, something's 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. Written by ---

Bickering step-siblings together 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, Kathryn 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 (a very adamant virgin with plans to only "wait until marriage"), and if he is able to accomplish this seemingly impossible task, he can have his way with Kathryn - the one woman whom he KNOWS he can not have. If he is unable to seduce the ice queen, however, Katherine gets his classic car. Written by J.J. Neal

A pair of unscrupulous siblings star in a sexy tale of seduction, revenge and conquest. After cleverly seducing and ruining the reputation of an unsuspecting classmate, the sparks fly when Kathryn poses the ultimate challenge to her insatiable stepbrother Sebastian: deflower the Headmaster's beautiful, virgin daughter Annette. If he fails, Kathryn gets his 1956 jaguar convertible, but if he succeeds, Sebastain gets to possess and bed Kathryn. The stakes are high, but for Sebastian, the payoff is feverishly irresistible and before the summer's over, no one will escape their relentless game of cat and mouse . . . until one of them is bitten by the most unlikely sensation of all . . . love. Written by Robert Lynch