I Rewatched Cruel Intentions and Sebastian is Kinda Awful… But Kathryn Kinda Isn’t

22 years ago, Cruel Intentions made its debut and polluted all that we knew about the teen drama genre. Filled with sex, an excellent soundtrack and a young, attractive cast, it was everything teens wanted from the 90’s.

Unfortunately, it’s premise has not stood the test of time. Sebastian is actually super creepy, Kathryn is nowhere near as awful as she is implied to be and Christine Baranski really should have had more screen time! Although, I’d be lying if I said that ending doesn’t still give me goosebumps.

Entangled in forbidden lust, ruthless step-siblings, Sebastian (Ryan Philleppe) and Kathryn (Sarah Michelle Gellar), play a wicked game of seduction with Sebastian’s latest sexual conquest. Not your typical teen love story, Cruel Intentions is a perverted exploitation of women and virginal purity… Yet, we are expected to sympathize with Sebastian, and demonize Kathryn.

Whilst Kathryn is set up as the antagonist, Sebastian is given a chance at redemption after falling in love with Annette (Reese Witherspoon) – the conquest in question. Is he worthy of this arc? Does he succeed in redeeming himself? The answer to both of which being an enormous no.

Sebastian is a major egoist with a severe lack of respect for his peers. He is cunning and merciless, thriving on the power of male privilege as he delights in his status as a womaniser. Of course, every teen love story of the 90’s has an obnoxious, self-absorbed jock-type who undergoes a life-changing transformation… However, Sebastian is utterly unlikeable from start to finish.

Not only does he take pride in his blatant assault on a juvenile Cecile (Selma Blair), his actions are more often than not guided by his incestuous lust for Kathryn. Red flags are present from the beginning, especially after he seduces his therapist’s daughter and uploads her nudes online because the former “was overcharging.”

Given that he’s supposed to be the hero of the film, Sebastian eventually sees the error in his ways, right? That’s why we should be rooting for him, isn’t it? Again, that would be a huge no. In fact, Sebastian obtains very little (if any) growth at all. Once he develops feelings for Annette, he rejects her advances, which is supposed to be his big ‘come to the light’ moment. Is it really necessary to praise him for making one decent decision in his life? Even after this, he still wagers with Kathryn and never once does he confess to Annette his reasons for pursuing her.

Keeping with high school movie tropes, Sebastian’s actions are (undeservingly) absolved by the end of the film. Over the 97 minute runtime, nothing that Sebastian does gives reason to believe that he is suddenly reformed. He is depicted as somewhat of a saint; ending Kathryn’s exploitative reign in the process.

On the other hand, there is Kathryn. She is by no means innocent – nor is she better than Sebastian – but it may be fair to say that she is wrongly vilified. Callous and with a compulsive need for control, Kathryn is deviously diabolical. A master of manipulation who hides behind her perfect catholic image, though ultimately, her bitterness stems from misogynistic hypocrisy.

The speech she gives on the double standards of sex is just as compelling and relevant today as it was back in 1999. Where Sebastian is celebrated for his womanising ways, Kathryn is condemned and outcast for exuding such confidence. You cannot help but empathise with her as she boldly calls out male liberty. From her monologue alone, Kathryn is a noteworthy influence for women.

“Do you think I relish the fact that I have to act like Mary Sunshine 24/7 so I can be considered a lady?” Kathryn undisputedly hits the nail on the head here. There is so much power in this statement, and Kathryn’s delivery makes her all the more enthralling when compared to her counterparts. Both Annette and Cecile are portrayed as naive and highly reserved – which is respectable of course – but Kathryn’s criticism of the male agenda gives her character more depth.

She is by far the most realistic – and relatable – character within the film because she does not want to conform to expectations. Even to this day, Kathryn gives a truthful and rejuvenated perspective on feminism. Completely vilifying Kathryn yet showing compassion for Sebastian sends a telling message on the cultural attitude towards women and sex. Yes, Kathryn is deceitful and harsh but remember how Sebastian was introduced to us? Perhaps if she channelled her energy towards the hypocrites, Kathryn could have had a much greater (and meaningful) redemption arc.

In retrospect, neither Sebastian nor Kathryn are ideal role models, but at least we have a deeper understanding of the latter. Sebastian is let off the hook way too easily and even has the last laugh; whereas Kathryn is punished for emulating the same energy as her stepbrother. Bitter, betrayed and wholly depressed, Kathryn deserves a little more affinity.

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