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Top 10 Cruel Intentions Moments

VO: Rebecca Brayton WRITTEN BY: Savannah Sher
This classic teen movie is celebrating its 20th anniversary in 2019. For this list, we’re looking at the best scenes from this twisted romantic drama. Our list includes the bet, the blackmail, Kathryn's triumph, that kiss, swimming, and more! Join MsMojo as we count down our picks for the Top 10 Cruel Intentions Moments.

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Top 10 Cruel Intentions Moments

This classic teen movie is celebrating its 20th anniversary in 2019. Welcome to MsMojo, and today we're counting down our picks for the Top 10 Cruel Intentions Moments.

For this list, we’re looking at the best scenes from this twisted romantic drama.

#10: The Bet

Based on 18th century French novel “Les Liaisons Dangereuses”, “Cruel Intentions” follows the sexual manipulations of popular and well-to-do step-siblings Kathryn Merteuil and Sebastian Valmont. Kathryn seeks revenge on an ex, while Sebastian wants to sleep with the headmaster’s virgin daughter to boost his reputation. The two make a wager over whether or not he’ll succeed, with Sebastian’s car and Kathryn’s body as the stakes. Both seductive and twisted, the scene establishes right away that our protagonists are also our villains, while laying out their perverse dynamic together.

#9: The Blackmail

When Sebastian discovers that Annette has been warmed about his womanizing ways, he decides to get revenge on the suspected informant. The man in question is Greg McConnell, a closeted football stud and Annette’s ex-boyfriend. So Sebastian sets him up, taking photos of him in bed with Sebastian’s friend Blaine, who’s in on the scheme. Using the photos, Sebastian blackmails Greg into praising him to Annette. It’s exceptionally cruel, and shows the elaborate and callous means that Sebastian and his friend will go to in order to achieve his intentions.

#8: Kathryn's Triumph

Kathryn Merteuil is a complicated and nuanced character, whose ultimate goal remains ambiguous to the audience throughout the story. She manipulates everyone around her, including Sebastian, and in this scene she reveals to him the complex ways in which she’s managed to get exactly what she wants out of the situation. She tells Sebastian that he’s “just a toy”, and lambastes his character. But this also marks a turning point in the film - we see the tears in Sebastian’s eyes which show that he is far more human and vulnerable than Kathryn could ever be.

#7: Kathryn Gets What She Wants

Kathryn is a master manipulator, and her weapon of choice is pretty clear. In this scene, she checks in with Sebastian, asking him if he’s succeeded in his seduction of Annette, and requesting that he help with her own mission: ruining Cecile Caldwell. Throughout this entire conversation, Kathryn is attempting a seduction of her own, teasing her step brother while she lies on top of him. You can decide whether this scene is steamy or just plain sadistic. Sure, the two are STEP siblings, but either way it’s pretty disturbing!

#6: Kathryn's Speech

For much of the movie, Kathryn may seem like a straight up villain, but at certain moments we get insight into her psyche that makes us sympathize with her - at least a little. In this scene, she explains her motivations to Sebastian, and as messed up as she is, there’s actually a pretty strong undercurrent of feminism at the core of her monologue. She explains how she resents the fact that she has to act a certain way as a woman, always appearing to be pure and innocent rather than showing confidence or sexual pleasure. Hey, maybe this story was actually ahead of its time.

#5: That Kiss

It wouldn’t be a list about “Cruel Intentions” without mentioning this memorable moment. As part of her epic take-down, Kathryn helps to usher in a sexual awakening in Cecile. This involves teaching her how to kiss, because of course it does. It’s a pretty sensual scene, and one that confirms that you do not want to watch this with mom and dad. In scenes like this one, you get the impression that Kathryn may actually want to help Cecile, and has forgotten about her ulterior motives. Also Sarah Michelle Gellar’s outfit in this scene is pure over-the-top perfection.

#4: Swimming

In his attempt to seduce Annette, Sebastian blares loud music into her bedroom, which tricks her into coming to find him in the pool room. It’s clear from the start that she is not amused by his antics, but faster than you’d think, he convinces her to hang out with him. This marks the turning point in their relationship, when she begins to fall for him. Sebastian does such a good job here that we almost start to believe him. Oh and the phone call that Sebastian has with Kathryn while Annette is getting ready? It may be brief but it’s hilarious.

#3: Annette Tries to Make Sebastian Laugh

Once they actually start spending time together, Annette and Sebastian have some great moments with one another. One of them comes when they’re driving in the countryside and Annette accuses Sebastian of taking everything too seriously. She starts trying to make him laugh by pulling ridiculous faces at him while he drives, and at first, he’s clearly not amused. His resolve quickly crumbles however, and he can’t help but smile at her when she won’t stop. It’s a cute moment that’s actually relatable in a movie largely filled with overly dramatic ones.

#2: The Escalator Scene

In the climax of the film, Annette has been hurt by Sebastian and plans to leave town to stay with a friend. He can’t let her go at this point however and waits for her at the top of an escalator at the train station. Despite everything we know about Sebastian, this moment is incredibly romantic, because it shows that he’s managed to truly change. The choice to use the song “Colorblind” by Counting Crows in this scene couldn’t have been more perfect. You’d better bet that this moment fueled a whole lot of teenage fantasies. And afterwards, Sebastian finally gets what he sought.

Before we unveil our top pick, here are a few honorable mentions.

Practice Makes Perfect

Sebastian Breaks Up with Annette

Ronald Response After Cecile's Mother Kicks Him Out

Sebastian Dies

"I Don't Trust Myself With You"

#1: Kathryn Gets What She Deserves

After Sebastian’s sudden and tragic death, Kathryn is one of the people to speak at his funeral. During her speech however, the crowd becomes unsettled and people start to leave as she’s still speaking. She goes outside to realize that someone has printed out copies of Sebastian’s journal, and Cecile hands her one with an innocent smile on her face. Inside are details of all of Kathryn’s exploits, which will not only ruin her relationships and her reputation but also her academic career. All of this, set to the bars of “Bittersweet Symphony” make for a perfect moment. Seeing Annette drive off in Sebastian’s car is just the cherry on top.

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