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5. Cruel Intentions

Sexuality was deeply explored in the 1999 teenage drama, Cruel Intentions, and it all started with a little wager between Sebastian (Ryan Phillippe) and Kathryn (Sarah Michelle Gellar; pictured). If Sebastian failed to sleep with Annette (Reese Witherspoon), he’d have to hand Kathryn the keys to his Jaguar. However, if he was able to get her into bed, he would get the opportunity to sleep with Kathryn, too. This spicy and sexy movie included all of the themes of a blockbuster smash, from blackmail to tangled webs, lies, deception, and sexual manipulation.

cruel intentions
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