Reese Witherspoon, Sarah Michelle Gellar and Ryan Phillipe star in this modernised adaptation of the classic French novel Les Liaisons Dangereuses starring good-looking young Hollywood types.
Phillipe plays handsome upper-crust New York teenager Sebastian Valmont, who has a mild obsession with his sultry step-sister Kathryn Merteuil (Gellar), principally because she is one of the few girls who doesn't fall at his feet.
When All American over achiever Annette Hargrove (Witherspoon) starts at their posh school, Kathryn takes an instant disliking to her and makes a bet with Sebastian. He must woo and bed and dump Annette - if he can, he gets Kathryn, if he can't, Kathryn gets his Jaguar.
But wouldn't you know it, despite his shallowness, Sebastian finds himself falling for Annette. At the same time more schemes come to life involving other characters such naive Cecile Caldwell (Selma Blair - Hellboy); gullible Ronald Clifford (Sean Patrick Thomas - Barbershop) and devious Blaine Tuttle (Joshua Jackson - Dawson's Creek).
Cruel Intentions is a deliciously enjoyable drama that manages to be sexy, funny, thrilling and romantic at the same time. Phillipe and Witherspoon have tangible chemistry which clearly spilled over into real life as the pair a currently married with children. And in a particularly sultry performance, Gellar establishes herself here as being capable of standing toe to toe with cinema's greatest femme fatales.
Cruel Intentions can even claim a degree of literary pedigree - Choderlos de Laclos' 18th century novel on which it is loosely based, has been adapted numerous times throughout the history of film. English playwright Christopher Hampton turned it into a play, upon which the most famous adaptation, the 1988 film starring John Malkovich, Glenn Glose and Michelle Pfeiffer, was based.
A television series based on Cruel Intentions named Manchester Prep was developed and even had several episodes shot, but then it was shelved at the last minute. The footage however, was sauced up and recut into a straight to video sequel entitled Cruel Intentions 2: Manchester Prep. That was enough of a success to generate a third film.