Cruel Intentions

Ryan Phillippe plays Sebastian Valmont, a wealthy and manipulative student who makes a wager to seduce a new girl at school.

Sarah Michelle Gellar portrays Kathryn Merteuil, Sebastian's cunning and ambitious step-sister who orchestrates their schemes.

Reese Witherspoon plays Annette Hargrove, the innocent new student who becomes the target of Sebastian's seduction.

Selma Blair depicts Cecile Caldwell, a naive and sheltered girl who gets caught up in Sebastian and Kathryn's plans.

Louise Fletcher plays Helen Rosemond, the strict and controlling head of the school who is also Sebastian's guardian.

Joshua Jackson portrays Blaine Tuttle, a friend of Sebastian's who is oblivious to the manipulations around him.

Eric Mabius plays Greg McConnell, a student who is romantically involved with Annette.

Sean Patrick Thomas depicts Ronald Clifford, a passionate and principled character who becomes entangled in the conflicts between the main characters.

Alaina Reed Hall plays the Nurse, a minor character in the film with little background information available.

Hiep Thi Le portrays Mai-Lee, another minor character with limited information on her role.

Deborah Offner plays Mrs. Michalak, a character who appears in a school setting.

Tara Reid portrays Marci Greenbaum, a character who contributes to the social dynamics of the film.