'Cruel Intentions' Did Not Age Well

Ryan Phillippe and Reese Witherspoon.
Ryan Phillippe and Reese Witherspoon. / Kevin Winter/Getty Images

My wife and I decided to have a throwback movie night this week and fired up a cult classic we both loved as pubescent teens, Cruel Intentions. For those who haven't seen the 1999 self-described "teen romantic drama," it follows a group of rich, unsupervised New York City minors whose lives intertwine in a series of coming-of-age moments, the biggest of which is a playboy trying to deflower the daughter of the new headmaster of their prep school.

Sounds fun, right? Horrifying is more appropriate.

Among the main social issues in this movie, homophobia, racism, incest, and sexual coercion of a minor are all prevalent and, in many cases, glorified.

Let's start with the "hero" of this movie, Sebastian (played by Ryan Phillippe). The movie starts with him meeting with his psychologist and, eventually, his psychologist finding out Sebastian slept with her daughter and posted naked photos of her on the internet. Today, we call that revenge porn and it's a serious crime. Back then, he gets a date with another girl as the mother/psychologist yells at him from behind a window.

Sebastian goes on to target a virgin he read about in a magazine as his next sexual conquest, Annette (played by Reese Witherspoon). Upon hearing this, Sebastian's drug-addicted, alcoholic stepsister Kathryn (played by Sarah Michelle Gellar) challenges him to a bet that Sebastian can't get Annette to sleep with him. If Sebastian fails, Kathryn gets his car. If Sebastian wins, he gets to have sex with Kathryn. At first Sebastian isn't interested in the stakes, as simply having sex with his step-sister isn't a payoff equal to the loss of his car. Then she says he "can put it anywhere" and the bet is on.

At the same time, Kathryn is mad at her ex-boyfriend and puts Sebastian up to the task of sleeping with his new girlfriend, Cecille (played by Selma Blair) as revenge. Cecille is just entering high school, estimated age 13 or 14. The step-siblings concoct a plan where Sebastian will seduce this incoming freshman in order to humiliate Kathryn's ex-boyfriend.

Sebastian is up to the task. He gets Cecille drunk. She doesn't know she's drinking alcohol. Then he tells Cecille he wants to give her a kiss. She agrees and puckers up. Then he says, "No, I don't want to kiss you on your lips, I want to kiss you 'down there.'" Cecille is rightfully horrified at the thought. Sebastian says he'll call her mom and tell her to come get her. The girl is scared because she's grounded, which Sebastian knows, and says no. Sebastian says about the kiss, "a promise is a promise" and then the inebriated Cecille agrees to oral sex even though she's not at the age of consent. The two later have sexual intercourse after Kathryn tells Cecille to use Sebastian as practice so she can please her music teacher.

Speaking of which, the music teacher, Ronald (played by Sean Patrick Thomas) is an aspiring cellist bound for Juilliard. Him and Cecille have a secret romance going via love letters (again, inappropriate). When Cecille's mother finds out about these love letters after Kathryn rats the two out, she's appalled because he's "so...black." She fires Ronald immediately and says he should have been more grateful because she "got him off the streets." He tells her he lives on 57th and Park. He quickly realizes she's a racist and leaves the apartment yelling, "The black man is gone!"

Meanwhile, Sebastian is on a rampage to steal Annette's virginity. He realizes a football player named Greg from his high school is from Kansas City, just like Annette, and tries to find an in. While talking with his homosexual friend Blaine (played by a yellow-haired Joshua Jackson) he finds out "the Gregster" has had sexual encounters with Blaine, but doesn't want anyone to know. Homophobic rhetoric runs rampant during their conversation and eventually the two agree to blackmail Greg by taking photos of him and Blaine having sex. The plan works, and Greg now works for Sebastian, spreading lies about him being a good person to Annette.

Annette and Sebastian spend time together and eventually do have sex after Sebastian tells her he loves her. He's being honest, surprisingly, but is soon tricked by Kathryn into breaking up with Annette, which he does by telling her the feelings he had are gone. Upon returning to Kathryn to "put it anywhere" he wants, she then tells him she was just toying with him to see if Sebastian would break up with the girl of his dreams. Seemingly, she has won.

Then, Sebastian decides he needs to make amends. He has kept a journal of all his sexual conquests, which he gives to Annette. She reads it and feels bad about what's happened, for whatever reason. She tracks him down but, unfortunately, he's locked in a fight with Ronald because Kathryn, who had sex with Ronald, lied to him and said Sebastian hit her. She also disclosed Sebastian had sex with Cecille, who Ronald is now having sex with (again, she is 13 or 14 years-old). In the fight, Annette gets thrown into the road and Sebastian dives and pushes her out of the way of a taxi. Sebastian is hit by the taxi and dies.

At a memorial on the first day of school, Kathryn is giving a speech about her stepbrother, but notices students walking out. She throws a hissy fit and follows them outside. Cecille then hands her a copy of Sebastian's printed out diary, which the entire school is reading and exposes her for what she is. Everyone hates her, she's caught by the headmaster with cocaine, and Sebastian is the hero.

It's a wild turn of events for a young man who has posted nude photos of an ex on the internet, did everything he could to steal a girl's virginity that he targeted and, most notably, coerced a minor into an inebriated sexual encounter, but that's how the movie went. It was a surprise to me and my wife as we watched it, having not realized at the time how offensive this movie was, and an eyeopener in terms of how much things have changed in the last 20 years.

Most of the jokes would have been laughed at in the late 90s. Today, you would be thrown out of Hollywood for making them. The sexual encounters were clearly deemed appropriate by the studio back then. Today, you would be thrown in jail for engaging in virtually all of these acts.

Sometimes movies withstand the test of time. Citizen Kane comes to mind. Cruel Intentions does not. It is one of the worst movies I've rewatched and I'm thankful I'll never have to again. One has to wonder how the stars of the movie feel about making it now.