Roger Kumble’s Cruel Intentions is a deliciously dark tale that isn’t afraid to go to extremes to tell its wild story. Based on Les Liaisons dangereuses by Pierre Choderlos de Laclos, and inspired by the 1995 movie Welcome to the Dollhouse, Cruel Intentions was originally intended to be an R-rated indie flick with a small budget. When Columbia Pictures picked it up, Producer Neal H. Muritz agreed to work with them as long as the movie would be nothing less than rated R–an interesting choice for a movie with that level of teen appeal, though understandable considering its content.
Cruel Intentions follows stepsiblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe) as they terrorize the Upper East Side with their antics. Sebastian is a known womanizing bad boy with a tendency to humiliate his conquests, while Kathryn hides her sociopathy (and cocaine habit) behind a spotless reputation as the student body president of Manchester Academy and mentor to new students. When Annette Hargrove (Reese Witherspoon) moves to town and reveals (via Seventeen Magazine, I might add) that she plans on staying a virgin until she’s married, Sebastian and Kathryn hatch a bet: if Sebastian can get Annette into bed, Kathryn will have sex with him. If he fails, Kathryn gets his 1956 Jaguar Roadster. Of course, Sebastian gets in over his head and proceeds to–and I mean this in the most dramatic way possible–lose his heart and his life in the process.
Cruel Intentions’s stellar cast helped save what could’ve been too polarizing a film. Witherspoon portrays Annette as someone deeply principled and steadfastly comfortable with herself without being holier-than-thou–despite what Sebastian may say. Consistently clad in cool, light colors, she’s genuine and nice without being a pushover–basically, the exact opposite of Kathryn. When Annette exposes Kathryn as the manipulative villain she is at the end of the movie (set to the sound of The Verve’s “Bittersweet Symphony”), she proves that she can beat Kathryn at her own game, though she won’t use her abilities for evil. On the other hand, Phillippe rides the wave of his unstable character arc. He ranges from insouciant and cavalier to devastated and ashamed, working his bone structure and boy band-esque pout to the best of his ability.
Witherspoon and Phillippe, engaged at the time, do a great job of showing the tumultuous, twisted love story that is Annette and Sebastian. The two had obvious chemistry, with Annette’s charms breaking down Sebastian’s walls. They eventually admit their feelings for one another, leading to a tender love scene set to the sounds of “Colorblind” by the Counting Crows. Their breakup scene is emotionally acted, with both of them in tears as Sebastian lies to Annette about his feelings and she slaps him–a scene so well done that Ryan Phillippe reportedly went outside and threw up after they filmed it.
While Witherspoon and Phillippe’s performances provide the backbone to Cruel Intentions, the movie would have been nothing without Sarah Michelle Gellar’s exquisite portrayal of Kathryn. With vicious instincts, a sharp tongue, and absolutely zero compassion for the people around her, Kathryn makes Queen bees like Gossip Girl’s Blair Waldorf and Mean Girls’s Regina George appear angelic. While Kathryn’s behavior is marked by selfish desires and malicious intent, you can’t deny that she makes one of the most important–and feminist–points in the whole movie. Addressing Sebastian, she snaps:
“It’s okay for guys like you and Court to fuck 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 fucking Brady of the Upper East Side, and sometimes I want to kill myself. So there’s your psychoanalysis, Dr. Freud. Now tell me, are you in… or are you out?”
Like everything Kathryn does, this quote is, as we say “A Lot,” but she makes a valid point about double standards and slut shaming. Kathryn’s prioritization of herself could be impressive if not for the whole sociopath thing. Kathryn only ever shows emotion and vulnerability when it’s affecting what she wants; there’s never any remorse for what she’s done, even after her actions indirectly lead to Sebastian’s untimely death. While the critical reviews were mixed, most praised Gellar, Phillippe, and Witherspoon for their performances, not to mention the appearances of Selma Blair as the naive, snotty Cecile and the indomitable Christine Baranski as her wealthy, domineering mother. Some outlets perfectly captured the successes of Cruel Intentions like The Chicago Sun-Times, which called the movie “smart and merciless in the tradition of the original story.” The movie won two MTV Movie Awards, including Best Kiss for Sarah Michelle Gellar and Selma Blair’s iconic scene. It inspired two more direct-to-home video movies–a prequel starring Amy Adams and a sequel–as well as a 2017 Off Broadway musical and a squashed reboot series on NBC. Cruel Intentions might be absolutely absurd in its twisted sex games and have some fairly noticeable plot holes (how does Annette end up with Sebastian’s car at the end of the movie? Inquiring minds STILL want to know!) but you can’t deny that the excellent performances and wickedly scandalous script with the perfect amount of profanity makes it compulsively watchable.