Roger Kumble’s Cruel Intentions flipped the script. There were no lovable nerds here. The protagonists were wealthy, beautiful, and sociopathic. Sebastian Valmont (Ryan Phillippe) and Kathryn Merteuil (Sarah Michelle Gellar) were the villains of every other teen movie, elevated to starring roles. They treated sex as a weapon, reputation as currency, and innocence as something to be devoured.

as Sebastian Valmont: The suave womanizer who eventually seeks redemption through love. Reese Witherspoon

: Known for its provocative themes and bisexual representation through Kathryn's character, it sparked conversations on power dynamics and teen sexuality that still resonate on platforms like Reddit today. Verified Facts & Trivia Release Date March 5, 1999 Director Roger Kumble Starring