Sebastian Valmont (Ryan Phillippe) is a handsome playboy sharing a life of privilege with his equally promiscuous step-sister Kathryn Merteuil (Sarah Michelle Gellar). The two are vain, arrogant, wealthy adolescents - often deliberately causing turmoil in the lives of others for their own amusement. They begin their most daring destructive game while their parents are in Bali, leaving them free rein to do as they please.
When the innocent daughter of the headmaster at their private school publishes an article on virginity, she unknowingly makes herself a target for Kathryn's scorn. Determined to sully the reputation of the chaste Annette Hargrove (Reese Witherspoon), Kathryn offers Sebastian a bet: bed the headmaster's virginal daughter and win Kathryn herself as a prize. If Sebastian loses, she gets his fully restored antique Jaguar.
Confident that the bet will serve as no big challenge, Sebastian seeks out interactions with Annette and finds that his reputation has preceeded him. She is cautious with him and remains devout in her belief that sex should wait until marriage. Sebastian grows more and more frustrated, finally resorting to letting down his defenses to earn her trust, but when he does so, he also leaves his heart unprotected. Without realizing it, he falls in love with Annette and when the opportunity arises for him to win the bet, he finds that he cannot betray her. Even after being ridiculed by Kathryn for his feelings for Annette, for once he is determined to follow his heart.
Ryan Phillippe is great as Sebastian Valmont - a devious philanderer with no concern for anything but his own satisfactions. His transistion after meeting Annette is a bit fast, but plausible. Sarah Michelle Gellar is really stunning in her role. She portrays the conniving, jealous Kathryn to a tee, and her sarcastic comments and witty jokes are perfectly timed. Selma Blair is also quite good as Cecile, the victim of one of Kathryn's slick destructive plans. Sean Patrick Thomas (Ronald) and Christine Baranski (Bunny), also share a very funny scene.
This movie moves well, is sexy and clever, and makes room for more than a few variations on the original story without becoming a totally different one. Perhaps one of the few disappoints in the film is just how long it took Reese Witherspoon to become a likable character. Initially she is rather bland. It isn't until much later we see good displays of emotion and a tender vunerability that fits her character perfectly. Although the sequels to this film (Cruel Intentions 2 and 3) left much to be desired, the original was all it was claimed to be: stylistic and hip.
Extra Extra! Tidbits About the Movie...
*In Reality - Reese Witherspoon and Ryan Phillippe were romantically involved during the filming of the movie and had their first child a year later.
*Best Line - Cecile says, "This sure doesn't taste like an iced tea." Sebastian responds, "It's from Long Island."
*Songworthy - "Bittersweet Symphony" - The Verve Pipe
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