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Cruel Intentions (1999), by the nature of its name, is a film that explores revenge, deceit, control, and the importance of appearances. The film follows step-siblings Kathryn Merteuil and Sebastian Valmont, who unforgivingly share a desire for power over their classmates. This desire usually manifests between them through sexual manipulation and malicious social moves. The characters Annet Hargrove and Cecil Caldwell round out the main ensemble. Annette provides the ultra-pure caricature of a desirable young woman ‘should be.’ Meanwhile, Cecil may be nieve and easily corrupted, but she also shares the innocent or ‘good girl trope.
With that said, the film is portrayed through a blatantly misogynistic lens. Regardless of the cast being primarily female, most of the storylines revolve around Sebastian; In fact, there are only two exchanges between women in the entire film that are not regarding a male character (( GWSS 3307 Feminist Film Studies. “Cruel Misogyny: What Really Was The Intention Of Cruel Intentions?,” 17 February 2016. )). Moreover, while almost every character displays unfavorable attributes, one of the most consistent themes in Cruel Intentions is internalized misogyny. A theme that, if avoided, would’ve changed the film’s trajectory entirely.
Cruel Intentions‘ (1999) Opening Sequence: The Therapist’s Daughter
The opening scene of Cruel Intentions is a great place to start to paint a better picture of Sebastian Valmont. The film opens with Sebastian lying on a familiar interpretation of the therapist’s couch. The camera nudges the audience that this particular therapist probably isn’t the best person and probably doesn’t care much about her patients. However, these events that would follow in this scene were surely unwarranted.
Sebastian’s therapist gets a call from her daughter sobbing, and she explains that someone had leaked nude photos of her onto the internet. Soon after, the audience learns that it was, in fact, Sebastian that performed this devious act, and he goes on to inform Kathryn that it was due to her overcharging. At any rate, Sebastian’s cruel intentions permanently affected an innocent girl’s life, and it would not be the first time or the last.
The Indirect Revenge On Court Renolds
Quickly Cruel Intentions sets up Kathryn’s backstory and connects it to fellow main character Cecil. In short, Kathryn was dating Court Renolds, played by Charlie O’Connell, until he dumped her over Fourth of July weekend for Cecil. To be clear, Cecil didn’t do anything wrong in this scenario, and the two of them dating did not overlap. Though, Kathryn felt that she gave Court everything and she would need to enact revenge. Unfortunately for Cecil, Kathryn has a ‘little miss sunshine’ image to keep up. While she is a mirror image of Sebastian, with arguably more depth and blatantly less character arch (thank you, male writers…), they seemingly lead very different lives. The reason, described best by Kathryn herself,
It’s okay for guys like [Sebastian] and Court to f*** everyone but when I do it, I get dumped for innocent little twits like Cecile. God forbid I exude confidence and enjoy sex. Do you think I relish the fact that I have to act like Mary Sunshine 24/7 so I can be considered a lady? I’m the Marcia f***ing Brady of the Upper East Side, and sometimes I want to kill myself. So there’s your psychoanalysis, Dr. Freud.
Kumble, Roger, dir. Cruel Intentions. Columbia Pictures, 1999.
Moreover, Kathryn has to hide certain parts of her life that her male counterparts get praised for because she is a woman. Thus, the ‘good girl’ facade and her decision to indirectly attack Court persist. She explains that she can’t have anything traced back to her and sets her sights on corrupting Cecil. Hoping to break Court’s heart was the motive, but seriously damaging Cecil was the game.
Cecil Caldwell
The summer before Cecil’s first semester at the new prep school, her mother recruits Kathryn to mentor her. In Mrs. Caldwell’s own words, the reason for this luckless pairing was due to “Kathryn [being] one of the most popular girls at school…”(( Kumble, Roger, dir. Cruel Intentions. Columbia Pictures, 1999. )). Consequently, she instructs her daughter to listen to and trust Kathryn, the girl who is actively trying to ruin her life. In reality, no one tried to stop Kathryn or even made it hard for her to pull off. Her mother constantly displayed an interest in Cecil’s and her own image, but not once did she display care for her feelings or actual well-being. Similarly, Sebastian knew what Kathryn was plotting and helped her execute almost everything.
While he does question her on whether she thinks ruining an innocent girl is taking it too far, the conversation doesn’t go far, and it’s because he didn’t need much convincing. It almost seems out of character for him to ask, knowing what the audience knows at this point. To pull this ‘revenge’ off, Kathryn first needs to gain Cecil’s trust. Obviously, Mrs. Caldwell offered a nice head start, but the viewer sees Kathryn and Cecil together a fair amount. Constantly hanging out with her, subtly pushing Cecil to tell her incredibly intimate things about herself, she is left here in a trap. The film implies that Kathryn nudges Sebastian to, in frank terms, sexually assault her. After this happens, Cecil confides in Kathryn, the girl she’s been told to trust, only to be gaslit and pushed back into the arms of her abuser.
While Cecil is ‘hanging out’ with Sebastian to, in Kathryn’s words, “practice for who she truly loves,” Kathryn is demolishing her chances with her actual love interest. She not only gets her mother to separate the two, but she also goes on to sleep with him. Cecil is without a doubt the purest and well-intended character, but due to the misogyny, internalized or not, she goes through the wringer. Due to her mother’s internalized misogyny, Cecil is left with no one to protect her. She is seen as a status symbol more than a human being. Kathryn is also angry with Court’s character, yet she takes it out on Cecil. A good portion of this could be attributable to her need to keep up a certain image. On the other hand, the extent that she takes it to exudes anger towards Cecil. Last but not least, Sebastian blatantly views and treats Cecil as an object rather than an actual human being.
The Bet Contrived Of ‘Cruel Intentions’
Early in the film, step-siblings Kathryn, played by Sarah Michelle Gellar, and Sebastian, played by Ryan Philippe, place a wager. For some reference, the ruthless pair matriculate at a prestigious Manhattan prep school, and this coming semester, they will have a new headmaster. As the story goes, Sebastian is growing bored with the sexual partners available to him within the student body; probably because he rejects any attempt at human connection and barely knows half of their names. Be that as it may, when he stumbles across Annette Hargrove’s manifesto in Seventeen Magazine, he sets his sights on a new challenge. Not only is Annette, played by Reese Witherspoon, the new headmaster’s daughter, but she is also a proud virgin waiting for ‘the one’ according to her article.
Finding his way into bed with Annette would not only serve as an interesting challenge to subdue his boredom, but it would also have him leaving school “a legend”(( Kumble, Roger, dir. Cruel Intentions. Columbia Pictures, 1999. )). In Cruel Intentions, the men who exploit and manipulate women for sex are seen as admirable by fellow male classmates and are somehow still seen as desirable by their female classmates. But, of course, there is more to it; the wager is placed due to Katherine’s genuine assumption that Sebastian won’t be able to pull it off. If Katherine wins, she gets his 1956 Jaguar Roadster. Knowing that he values his car greatly, she offers up her own body to Sebastian, the one ‘thing’ he wants yet can’t have. If you haven’t caught on by now, they’re a pretty screwed-up duo. Regardless, with Katherine on the table, Sebastian accepts. Though it’s safe to say he had no idea what he was getting himself into.
Annette Hargrove
Annette unknowingly enters the cruel sibling’s arena as a pawn as Sebastian eagerly begins in his attempts to get her into bed. At this point, he is portrayed with no remorse insight, similarly to how we are introduced to him. Though, with no surprise to the audience, she resists Sebastian, considering Annette’s view on sex. Of course, the bet is still on, so he persists and, in the meantime, gets to know her. Something easy to assume he has never done before.
Shortly, they fall in love even though Sebastian manipulates Annette most of the time. Sebastian might’ve also confused love for positive human connection with a female, but who’s to tell. At this point in the film, they seem really in love or infatuated, but it feels natural in some significant manner. Following this realization, arguably still through manipulation, they decide to sleep together. This is one of many sex scenes in the movie, but it’s the only one that portrays any level of intimacy. They are in love, despite the odds, but remember that bet? Kathryn is portrayed as many things in Cruel Intentions, but one of them is not a loser. Despite his love for her, she can get into Sebastian’s head and make him leave Annette.
This results in him giving her his journal, his prized possession, detailing the bet and presumably everything else of importance that occurred in his life. Unfortunately, the next day Sebastian dies, due to a freak accident in which he happens to get into a fight on the street with a man that Kathryn sent after him, not to kill him! When Annette sees the fight and tries to break it up, she is pushed in front of a car. Consequently, Sebastian loses his life trying to save Annette’s and at his memorial, Annette teams up with Cecil to disperse copies of the journal. They intend to ruin Kathryn, which in Cecil’s case is incredibly understandable, but while Kathryn was involved in the bet and the breakup, she never aimed to hurt or root against Annette. Therefore, the decision to release the journal, which truthfully was entirely up to Annette, doesn’t make much sense. Furthermore, she tore another woman down when she found out about the entire mess but still claims loyalty to Sebastian. Irrefutably, Sebastian had far worse intentions for Annette, but Kathryn remains the sole villain.
Kathryn Merteuil
It’s essential to note Kathryn’s thought process, in full, regarding the bet in Cruel Intentions to understand her character a little better. As previously stated, Kathryn never intended to hurt Annette, not that she cared if Annette got caught in the crossfires. In reality, she wanted to hurt Sebastian. The misogynistic lens illustrated by the film would have you believe that Kathryn is a shrew and she enjoys others’ pain. That is simple enough to see in the way that Kathryn is so similar to Sebastian, who self-admittedly enjoys causing others pain. Though, where Kathryn differs is in the fact that when she does perform acts with cruel intentions, at least in the film, she has a motive. Usually, a rationale stems from her being hurt.
It would not be unbelievable to conclude that Kathryn, a smart girl, could see how Sebastian simply valued her for her looks. But, also knowing that Sebastian wanted her more than anything, she made the bet. With the odds in her favor, she would anticipate taking a prized possession from Sebastian. A man who she didn’t respect because he had no respect for her. However, the plot thickens when he is, in fact, successful. Remember, Kathryn is not going to take the loss. A reoccurring theme for Kathryn’s character is that she is “always dumped for the innocent twits”(( Kumble, Roger, dir. Cruel Intentions. Columbia Pictures, 1999. )). It is clear down to the costume design that portrays its ‘good’ or innocent characters in primarily light and pastel colors. The film dresses the less formidable counterparts in dark clothes and more scandalous attire. Of course, Kathryn portrays the latter, while Annette is seen in pastels. So, when Sebastian succeeds with Annette and falls in love with her as well, it hits multiple layers.
Kathryn doesn’t respect Sebastian, and if she was hoping to see him squirm, he found love instead. At the same time, she knew once he had moved on from wanting her, she could no longer hold anything over him. Not to mention it was a blow to her confidence and she was yet again dropped for the innocent option. This time, the only person she believed would never pick the naive option. So she aims to break up Annette and Sebastian with the sole purpose of hurting him. Not only that but triumphing over him, hoping that she would feel the pain he caused her. Sebastian’s death was nothing but a freak accident, and while Kathryn intended to cause him pain, the release of the journal still seems unwarranted, at least by the hands of Annette.
Cruel Intentions‘ Bittersweet Symphony
Roger Kumble, the director of Cruel Intentions, fought hard to have the song “Bittersweet Symphony” by The Verve appear in the final scene. This was because he felt it captured the mood perfectly, and it’s safe to say many fans agree. It does feel like a bittersweet ending. One could feel happy for Cecil because she has a part in taking Kathryn down. Though after that, it’s mostly bitter. Annette drives off into the sunset, and it feels like the viewer should be happy for her too, but she was relentlessly lied to and manipulated.
The audience watches the crumble of Kathryn’s reign but despite her terrible actions, it doesn’t feel great. Maybe this is because Annette is responsible, which still doesn’t make much sense. Though it would be safe to say the most bitter realization that comes from the film rounding out is that three female leads just danced around each other, plotting against each other in the interest of blatantly terrible men. Each of these young women could have avoided the conflict entirely if they had just taken a look around and realized who angered them. Therefore, to these ladies’ detriments, Cruel Intentions is riddled with misogyny, internalized or not. Thus, the film probably wouldn’t exist without this lens because it acts as an integral crutch.
