Cruel Intentions

Cruel Intentions starred Sarah Michelle Gellar, Ryan Phillipe, Reese Witherspoon, Selma Blair, and Joshua Jackson in this tale of teenage depravity, and they eat up every second of screen time they have.

Much like the ‘80s, a slew of ‘90s teen idols played against one another in multiple productions. Reese Witherspoon and Selma Blair were both in Legally Blonde, Sarah Michelle Gellar and Ryan Phillipe were both in I Know What You Did Last Summer, and Sarah Michelle Geller, Selma Blair, and Joshua Jackson were all in Scream 2. Granted, the latter two in Scream 2 were bit parts, and Selma Blair was uncredited. It still counts. Even Tara Reid and Joshua Jackson, having recently filmed Urban Legends, were brought back together here. This kind of camaraderie allowed for greater chemistry to brew between the actors, stemming from their real-life friendships and rapport. Even when Ryan Phillipe and Sarah Michelle Gellar are sniping with one another in character, the tension is palpable. Is it any wonder that their characters were in a relationship in I Know What You Did Last Summer?

Like many teen films from the ‘90s, it all starts with a desire for revenge and a callous bet, and it ends in redemption and well-deserved karma. Kathryn Merteuil (Sarah Michelle Gellar) is upset that her ex-boyfriend Court Reynolds (Charlie O’Connell), has dumped her for another woman, Cecile Caldwell (Selma Blair), an incoming freshman at the private school they all attend. Her stepbrother, Sebastian Valmont (Ryan Phillipe), is central to her schemes to get back at him, but his refusal brings out his own schemes to seduce Annette Hargrove (Reese Witherspoon), the daughter of their new Headmaster, who was recently featured in an article regarding her decision to practice chastity until marriage. Sensing a deal can be struck, Kathryn promises to have sex with Sebastian if he succeeds but gets his car if he fails. By then, it’s clear that Kathryn has her eyes set on destroying Cecile by herself.

Each character has their share of secrets, whether it be Kathryn’s cocaine use or Cecile’s relationship with her music teacher Ronald (Sean Patrick Thomas). Cecile’s mother, Mrs. Caldwell (Christine Baranski), is horrified when Kathryn exposes this secret to her – and while he is black, I think it would be a bit more of an issue that he’s forty years old. Cecile, mind you, was a freshman in high school – fourteen, at best. It’s clear that Kathryn doesn’t expose this secret for Cecile’s benefit, as she and Sebastian immediately use it to manipulate her throughout the latter half of the film. Then again, there are very few pieces of television and film that outright condemn student-teacher relationships unless it’s critical to the plot line that somebody is punished.

None of the characters are who they are initially presented as, reminding the viewer that people truly are complex beings. Sebastian’s habit of writing in his journal hints at what he could be doing with his life. Kathryn hides behind her religion, and a façade of purity, yet her cocaine is literally hidden within the cross that she always wears. One has to wonder if Annette is far vainer and prouder than she lets on regarding the piece she writes for Seventeen magazine. Regardless, it was truly rewarding to see her own sexuality and not let it be used to shame her. She is also the one who ultimately brings Kathryn down, utilizing the last gift Sebastian ever gave her to do it, no less.

Cruel Intentions was like most films of the decade, full of attractive young actors who were renowned for their television roles or, in the case of some of them, their robust film careers. It was also full of casual homophobia, which was the norm in film and television until relatively recently. One notable plotline is Sebastian’s manipulation of Greg (Eric Mabius), who is Annette’s friend, and undoubtedly the one who alerted her to Sebastian’s womanizing ways.

Greg is in the closet and has a secret relationship with Blaine (Joshua Jackson), which Sebastian captures photographic evidence of and threatens to expose if Greg doesn’t assist in Sebastian’s attempts to seduce Annette. With little recourse, of course, Greg helps with a handful of casual slurs to boot. However, why this tends to work in this context is that Sebastian, Blaine, and Kathryn, for that matter, are terrible people who are only out of themselves. What’s a little homophobia when you’re a few steps down from being a sociopath? The late ‘90s were a difficult period, as LGBTQIA+-related issues and topics were still taboo. By the mid-2000s and early 2010s, these scenes were all but gone unless used by an overtly villainous character. Time will tell how well it will be remembered.

These storylines were commonplace, but they have had their time in the sunlight and have been put to bed. Now, a movie or television show is more likely to pause itself to address these kinds of comments head-on without the ambiguity of who is right or wrong. In the context of the film, Sebastian’s close friendship with Blaine goes a long way to show that he isn’t homophobic, and it was as meaningless as your everyday teenager throwing around ‘gay’ until it became apparent how harmful that could be. Mind you, Kathryn never did that – and she was the clear villain. Her foibles were far worse, in my opinion. Valencia Perez might like to speak with Kathryn regarding how Women Gotta Stick Together.

As a film, Cruel Intentions was not trying to break down barriers or redefine the genre. It provided a dark and gritty contrast to films like Clueless, and She’s All That, the former about a group of wealthy teens in a slice of life and the latter featuring a notorious bet that shakes up things in the third act. Films aimed at teens in the ‘90s covered darker storylines and themes, building off of the momentum started by their ‘80s counterparts.