A teen no more
Titillating classic Cruel Intentions launched many careers 20 years ago
In the summer of 2008, ahead of its season 2 première, The CW launched a controversial ad campaign for its defining series, Gossip Girl. It cleverly embraced its scathing reviews, with posters and commercials featuring its pretty young cast scantily clad, in mid-throes of passion, with choice criticisms splashed alongside them, including: “Every parent’s nightmare” (Boston Herald); “A nasty piece of work” (New York Post); “Mind-blowingly inappropriate” (Parents Television Council).
Those same critiques could be applied to the 1999 classic Cruel Intentions, now celebrating its 20th anniversary, a contemporary take on the 1782 novel Les Liaisons dangereuses that, at the time, was considered as saucy as saucy could be.
In an effort to keep up with the times, Cruel Intentions pushed things just a little further. Step-siblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) make a bet: If he can deflower the new headmaster’s daughter Annette (Reese Witherspoon), Kathryn will finally give in to their urges and sleep with him. If he loses, she wins an arguably better prize: his Jaguar. Thrown into the mix is Selma Blair as Cecile, now dating Kathryn’s ex. In other words, the film is rife with manipulation, vengeance, corruption (of the moral and sexual kind), and a touch of sort-of incest.
But like Gossip Girl, which aired on a relatively tame teen network, there isn’t much nudity to be seen in Cruel Intentions. The scintillation comes from the debauched narrative and dialogue (filthy, but smart and acerbic), where hands travel just off screen, made all the more delicious thanks to its photogenic ’90s stars’ titillating turns.
Philippe and Gellar operate at their peak, perhaps best playing evil, while Witherspoon’s impressive career playing plucky was only just getting started.
But it didn’t receive its milestone status entirely due to its naughty nature. It was at the epicentre of seminal millennial culture, not only with its cast, but its behind-the-scenes drama (Witherspoon and Philippe were a major tabloid couple at the time), imagery (one of the most iconic kisses in film history, between Gellar and Blair), style (Philippe’s black turtleneck and glasses, Witherspoon’s blue bathing suit) and, of course, its soundtrack.
The film opens with Placebo, has Sebastian and Annette succumbing to their tension to the tune of Counting Crows, and ends with The Verve’s Bittersweet Symphony. Blur, The Cardigans, Aimee Mann and Fatboy Slim are scattered in between.
It somehow expertly juggled Shakespearean drama with modern teen angst in the way of fellow young adult classics 10 Things I Hate About You, O and She’s the Man.
But, as any film that has been able to breathe for two decades or more, Cruel Intentions is not without its issues under the glaring spotlight of 2019.
A key subplot follows high schooler Greg, who Sebastian blackmails into manipulating Annette. In exchange, he says, he’ll keep Greg’s secret — that he’s gay, a word itself that is used numerous times throughout the film as an insult. Then, there’s that whole other subplot with Cecile’s piano teacher (Sean Patrick Thomas), whose race is his defining trait, and is used against him when he’s ousted from her life, and is later used as a pawn. To put it simply, the film’s commentary on class is as blatant as its countless metaphors.
But where Cruel Intentions succeeds and really shouldn’t is in its commentary on sex. As relevant now today as ever when it comes to double standards, its most iconic line, scathingly delivered by Gellar in a moment that defined the decade, is when she gives Sebastian a talking to: “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 f--king Brady of the Upper East Side, and sometimes I want to kill myself.”
Call it ahead of its time. Without it, there would be no Gossip Girl, The O.C., Riverdale or even Real Housewives. The ante would never have been upped because it never would have existed.