Ryan Phillippe and Selma Blair in Cruel Intentions (1999)

Ryan Phillippe in Cruel Intentions (1999)

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

Sarah Michelle Gellar and Selma Blair in Cruel Intentions (1999)

Joshua Jackson and Eric Mabius in Cruel Intentions (1999)

Ryan Phillippe and Reese Witherspoon in Cruel Intentions (1999)

Reese Witherspoon in Cruel Intentions (1999)

Sarah Michelle Gellar in Cruel Intentions (1999)

Ryan Phillippe and Ginger Williams in Cruel Intentions (1999)

Ryan Phillippe, Reese Witherspoon, and Sarah Michelle Gellar in 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)