Cruel Intentions (1999)

"Cruel Intentions" is a 1999 American teen drama film directed by Roger Kumble. It follows the manipulative and deceptive schemes of wealthy step-siblings played by Sarah Michelle Gellar and Ryan Phillippe, who make a wager involving seducing an innocent girl portrayed by Reese Witherspoon. The film explores themes of betrayal, lust, and power dynamics among privileged teenagers in New York City.