Cruel Intentions

Cruel Intentions is a 1999 feature film starring Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon and Selma Blair. It was based on the 18th century French novel Les Liaisons Dangereuses, but unlike other modern film versions of the novel (such as Dangerous Liaisons and Valmont), Cruel Intentions was set among the wealthy teens of modern-day New York society (though the principal cast members were all in their twenties). The film was released on March 5, 1999.
The plot concerns a bet made between Kathryn Merteuil (played by Gellar) and her stepbrother Sebastian Valmont (played by Phillippe). Sebastian must seduce Annette Hargrove (played by Witherspoon), a virgin and the daughter of the head master of the private school that the three attend. If Sebastian wins, his wish is to sleep with Kathryn. If he fails to do so, Kathryn receives Sebastian's car, a 1956 Jaguar XK140.
At first, Annette is repulsed by Sebastian, claiming she has a boyfriend and that she has been well informed of his reputation. She refuses to tell him who has badmouthed him. After visiting his friend, Blaine (Joshua Jackson), an open homosexual, Sebastian discovers that Greg (Eric Mabius), a popular, all-star football player at their school, is from Kansas City, as is Annette. This leads Sebastian to believe that Annette's informer must be Greg. Sebastian also learns that Greg is a closeted homosexual secretly involved with Blaine. He decides to blackmail Greg. However, after walking in on Greg and Blaine in bed together, Sebastian discovers that Greg is not the culprit. However, in exchange for Sebastian's silence, Greg talks to Annette and lies that Sebastin's reputation is false, and that he is really a nice guy. Annette begins to reconsider.
In the mean time, Kathryn concerns herself with Cecile Caldwell (Selma Blair), a young, naive freshman who looks up to Kathryn. However, instead of acting as a role model, Kathryn plots her revenge on Cecile, as Kathryn's ex-boyfriend, Court Reynolds, left her in favor of Cecile. Cecile doesn't know that Kathryn previously dated Reynolds, however she seems to be more interested in her music instructor, Ronald, an older, middle-class, black man. Kathryn tells Cecile to sleep with as many guys as possible in order to satisfy Ronald. Kathryn instructs Sebastian to seduce and deflower Cecile, which he does after discovering that Annette's informant is Cecile's mother, Bunny. Kathryn double-crosses Cecile, and tells Bunny Caldwell about their relationship, which she abruptly confronts and fires Ronald over. Kathryn has a brief tryst with Ronald, before he ends it to be solely with Cecile secretly.
After working his way into the heart of Annette, Sebastian tells her that true love is right infront of her and that she is a hypocrite if she turns her back on it now. Annette then begins to undress, preparing to have sex with Sebastian. But, just as he's about to win his bet with Kathryn, Sebastian says that he can't and leaves. Sebastian then realizes that he himself has fallen in love with Annette and this is no longer a bet.
The following morning, Kathryn wakes Sebastian and informs him that Annette has left to stay with friends, obviously displaying that Annette has reconsidered. After finding out Annette's whereabouts from Greg, Sebastian tracks Annette down at a train station where they embrace. Sebastian and Annette then have sex in Sebastian's bed, winning him the bet.
Kathryn overhears Sebastian and Annette on the phone, with him telling her he loves her. Kathryn tells him that she knows that he is really in love with Annette. He says that it's just a bet and that he has feelings for Kathryn. To prove this, he goes to Annette and lies to her, telling her she was "just a conquest." Annette becomes upset, crying and slapping Sebastian, before throwing him out of the room and breaking down. Sebastian then goes to Kathryn, telling her that he left Annette for her. She in return tells him that he was just a toy and that she wants nothing to do with him. He storms out in sure of the woman he really loves, Annette.
When Sebastian goes to her, she refuses to see him, so he leaves her his journal, which details Kathryn's real personality, the bet, and Cecile. However, Kathryn calls Ronald and lies that Sebastian hit her and reveals that he also had sex with Cecile. He goes to look for him. As Sebastian is walking to meet Annette, he is met by Ronald and the two begin to fight in the street. Annette sees this and goes to help Sebastian, and is knocked into traffic. As she is about to be hit by a taxi, Sebastian knocks her out of the way and is fatally hit by the taxi. His last words to her are "I love you."
The next scene is Sebastian's funeral. Kathryn is shown getting ready for her speech, while snorting cocaine in the bathroom. Annette enters (the first time the two are shown face to face) and offers her sympathy, which Kathryn shrugs off. As Kathryn is delivering her speech, while lying about her high morals, she notices several people walking outside. When she goes outside to see what's going on, she's handed a copy of the journal by Cecile, appropriately titled "Cruel Intentions." The headmaster approaches her and pulls apart her crucifix, revealing the cocaine. The last scene shows Annette driving away in Sebastian's jaguar with the original journal in the passenger seat.
Cast
Ryan Phillippe - Sebastian Valmont
Sarah Michelle Gellar - Kathryn Merteuil
Reese Witherspoon - Annette Hargrove
Selma Blair - Cecile Caldwell
Sean Patrick Thomas - Ronald Clifford
Louise Fletcher - Helen Rosemond
Joshua Jackson - Blaine Tuttle
Christine Baranski - Bunny Caldwell
Eric Mabius - Greg McConnell
Swoosie Kurtz - Dr. Regina Greenbaum
Tara Reid - Marcie Greenbaum