Ryan Phillippe and Sarah Michelle Gellar in Cruel Intentions (1999)

Sarah Michelle Gellar in Cruel Intentions (1999)

Ryan Phillippe, Reese Witherspoon, and Sarah Michelle Gellar in Cruel Intentions (1999)

Ryan Phillippe and Reese Witherspoon at an event for Cruel Intentions (1999)

Ryan Phillippe, Reese Witherspoon, Sarah Michelle Gellar, and Selma Blair at an event for Cruel Intentions (1999)

Reese Witherspoon at an event for Cruel Intentions (1999)

Sarah Michelle Gellar at an event for Cruel Intentions (1999)

Ryan Phillippe stars as Sebastian Valmont

Reese Witherspoon stars as Amanda Hargrove

Sarah Michelle Gellar stars as Kathryn Merteuil

Ryan Phillippe, Reese Witherspoon, Sarah Michelle Gellar, and Selma Blair in Cruel Intentions (1999)

Director Roger Kumble with stars Sarah Michelle Gellar and Ryan Phillippe

Jessica Alba at an event for Cruel Intentions (1999)