When it come to late 90s teen drama, few films are as memorable as Cruel Intentions. A big budget film that started out as an indie feature, became a box office success, and featuring a cast who was largely never heard from again, the back story behind Cruel Intentions is interesting enough, but the story itself is on another wavelength of fuckery™ that had, at the time, never been seen by movie-going audiences before and was so thoroughly captivating that the movie is still and will forever be one of my Messy Faves™. Adapted from a late-18th century French novel about the most morally bankrupt and bored White people you could ever hope to read about, this romantic drama is the tale of the most morally bankrupt and bored White people you could ever hope to see onscreen.
The film revolves around the highly dysfunctional relationship of step-siblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe), exceedingly rich and grossly unsupervised teens who love to play games of manipulation with other people’s lives. Each time they manage to destroy another person, the pair up the ante, and Sebastian details their various escapades in his closely guarded journal. Their new adventures include Kathryn’s take-down of the naive young virgin, Cecile (Selma Blair), the girl her last boyfriend, Court Reynolds, dumped her for, and Sebastian’s seduction of Annette (Reese Witherspoon), a not-so-naive young virgin who prides herself on abstinence until marriage.
Using Cecile’s ignorance of her previous relationship with Court and posing as a friend, Kathryn conspires to sabotage Cecile’s relationship with Court, as well as her burgeoning romance with her music teacher, Ronald (Sean Patrick Thomas). At the same time, Kathryn has a bet going with her step-brother, one which promises that she will have sex with him after years of flirting and heavy petting, should he succeed in having sex with Annette, and that she will have his vintage Jaguar if he fails to. If it isn’t already painfully obvious, Kathryn is incredibly busy minding other people’s business. The twisted siblings grow apart as what begins as a cruel game becomes much more serious when Sebastian realizes that hes’s falling in love with Annette. Read: This dramatic ass movie gets even more dramatic.
Cruel Intentions is so messy in a plethora of ways. Thomas’ role as Ronald, the young Black buck passed between two racially-fetishizing Beckies™, used to ruffle the feathers of diet-racist™ White parents is the only thing more annoying than the poor use of Joshua Jackson (indisputably the best actor in the entire cast) as the woefully under-developed Blaine, the token gay friend whose weaponizes his sexuality and relationship with a closeted gay man to help alleviate cishet boredom. Of course, the heavily-hinted pseudo-incestuous relationship between Kathryn and Sebastian (one subconsciously enhanced by the fact that Gellar and Phillippe were cast as lovers just two years prior in I Know What You Did Last Summer), and Gellar and Blair’s on-screen kiss, clearly a move to pander to middle-aged men, were all just part of the the most delicious set of shenanigans.
Though most of the target characters in Cruel Intentions were largely unintelligent (*cough* Cecile *cough*) and easily manipulated, with most of their troubles being wholly avoidable by doing the sort of investigation and busybodying that Kathryn had turned into an art form, the undeniable chemistry between both Gellar and Phillippe, and Witherspoon and Phillippe was scorching hot and made up for a multitude of cinema sins. One can’t help but roll their eyes every time Selma Blair speaks or “acts”, or wonder whatever became of Ronald after he was unwittingly used to fight a White woman’s battles, but Cruel Intentions is so addictive, and one of the few movies I will watch whenever it’s on. Featuring a brilliant score, excellent soundtrack, and the best of washed-up 90s royalty, this is one of the most deeply memorable family dramas ever acted out.
I give this one 4 stars.