Cruel Intentions (1999) 20th Anniversary

Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. The stakes are highwhen the duo agrees upon a deliciously diabolical wager of sexual conquest without consequences. The pawns? The naïve Cecile Caldwell (Selma Blair) and the virginal Annette Hargrove (Reese Witherspoon).