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Countdown of my top 50 favorite movies continues (#47)
#47
CRUEL INTENTIONS

A movie all about love, lust, and betrayal. Before there was Gossip Girl, Cruel Intentions was the first popular mainstream film to focus on the lives of spoiled brats from Manhattan’s upper east side. The story focuses on our main character, Sebastian. Sebastian is essentially, a male whore. He spends his time bedding a string of women; using them for sex and nothing more. He is rich, powerful, and more than anything…bored. So this is how he chooses to occupy his time.
His step sister Kathryn is equally trampy. She uses her alluring presence and dominating sexuality to get what she wants. She also happens to be a coke addict.
As the movie begins, we see what kind of twisted relationship these two siblings have. One that is also riddled with bizarre sexual chemistry. Kathryn reads an article about the headmaster’s daughter, Annette, and her goal to remain a virgin until she falls in love and gets married. Intrigued by this, Kathryn makes a bet with Sebastian that he can’t deflower Annette before the new school year begins. If he can’t, Kathryn wins and she gets Sebastian’s classic, vintage Jaguar car. If he is successful and wins, he gets something that he’s always wanted…Kathryn…in every explicit sexual position imaginable.
Sebastian accepts the challenge. He is tired of bedding the same old bimbos around New York anyhow, and jumps at the opportunity to deflower a virgin. However, to his surprise, the feat is much harder than he thought it’d be. Annette is adamant on sticking to her morals. What’s more, the more time Sebastian spends with Annette, the more he begins to genuinely like her. She makes him laugh and he feels comfortable and at ease around her. To his surprise he ends up falling in love with her…something neither of them were prepared for. What now? Does he continue with the bet or does he call the whole thing off?
In the midst of this bet, Sebastian has agreed to submit to another request by Kathryn. He’s agreed to sleep with Cecile: a girl who stole Kathryn’s boyfriend, Court, away from her. The plan is to turn Cecil into a sleazy tramp to get even with Court for choosing her over Kathryn. This subplot offers some pretty hilarious moments and it also blends in nicely with the main plot.
Overall, this is a great movie all about power and seduction. And it all builds up to a startling climax.