Cruel Intentions is the type of teen movie you probably watched and thought to yourself, "Should I, a teen, be watching this movie?" The iconic 1999 movie follows an apathetic prep school student Sebastian Valmont (Ryan Phillippe) and a bet wagered over new student Annette Hargrove (Reese Witherspoon). To no one's surprise, the bet doesn't go according to plan. Oh, there's also some very questionable step-sibling interactions that would make Clueless's Cher and Josh shudder.