Columbia Pictures
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Cruel Intentions was a seductive teen drama that sexualized an entire generation with its strong sexual references, steamy make-out sessions, and sexual blackmail. The 1999 film told the story of rich Upper East Side siblings Sebastian and Kathryn (Ryan Phillippe and Sarah Michelle Gellar) who make a bet to seduce the campus prude (played by Reese Witherspoon). In the process, things get very hot and heavy. Here's what the film had to teach us.