Before Gossip Girl, before NYC Prep, before Rich Girls and before Avery Singer gave her mom Ramona tough love fashion advice on The Real Housewives of New York, there was Cruel Intentions. The prep school version of the French classic Dangerous Liaisons starred a raven-haired Sarah Michelle Gellar as an Upper East Side queen bee named Kathryn who challenges her hook-up buddy/step-brother Sebastian (Ryan Phillippe) to sleep with the new school headmaster’s virginal daughter Annette (Reese Witherspoon).
It was a buzzy hit because it more than delivered on the promise of its title. Was the racy content inappropriate for teens? Wildly so. Was it also smart, sexy and maliciously entertaining? Big yes! And though 20 years have passed since its March 4, 1999 release, the slick flick remains a not-so-guilty pleasure. Grab a Long Island iced tea and read the reasons why.
1. Reese and Ryan
Yeah, fine, Witherspoon and Phillippe filed for divorced in 2006 and have since moved on. Good for them! Whatever! There’s still swoon-worthy gold in watching the two fair-haired actors — only in their early 20s at the time — fall in love with each other both on and offscreen. The breakthrough moment happens after Sebastian decides to accompany Annette to volunteer old age facility in a bid to win her over. It doesn’t go well. But during the drive back to New York City, the two start to connect. Their bond is sealed when Annette makes funny faces at him and his sullen veneer begins to crack. That wasn’t acting, friends.
2. The Kiss
“Haven’t you ever practiced on one of your girlfriends? It’s not gross. How else do you think girls learn?” And with that slithering encouragement, Kathryn takes off her chic sunhat, instructs her mousy new disciple Cecile (Selma Blair) to wet her lips, close her eyes,] and get ready to go to first base. At the time of Cruel Intentions’ release, the kiss between Gellar and Blair — which takes place on the Great Lawn in Central Park — was considered rather naughty, naughty. But in retrospect, the scene is just flat-out alluring. It’s also a highly charged example of Kathryn’s villainous machinations. Just consider how, post-kiss, she suddenly snaps her head back to her usual self while Cecile desperately waits for more. Exactly.
Fun fact: Witherspoon and Phillippe were supposed to do it to a Smashing Pumpkins song called “To Sheila,” but cranky lead singer Billy Corgan refused to give over the rights. Enter Adam Duritz of the Counting Crows, who saw a rough cut of the movie and offered to write and record the ballad “Colorblind.” Now it’s impossible to imagine hearing anything but those melancholic piano scales as Annette travels up the escalator at Penn Station and sees Sebastian patiently waiting at the top. The ultra-romantic and passionate bedroom scene ensues. And, ahem, their daughter Ava Phillippe ensued six months after Cruel Intentions’ release.
4. The Selma Blair Hair Flip
A mini-homage here to Blair, who’s been in the news lately because of her brave battle with Multiple Sclerosis. The actress may be older than Gellar and Witherspoon, but she convincingly played a doe-eyed freshman with legit comedy bravura. The eye-rolls, the pouts, the vigorous head-shakes. But most impressively, her Cecile goes from naïve follower to smirking, sneering grown up thanks to one fantastically timed hair flip. The magic happens right after she flings a copy of Sebastian’s tell-all journal to Kathryn in the middle of Sebastian’s funeral. Cecile turns on her heels, and Kathryn’s jig is up as a sorrowful do-gooder. All that’s left is for school officials to spill out the cocaine stashed in the cross on her necklace. Annette ends the film as a grieving girlfriend; Kathryn ends it as a victim of her own ego; Cecile ends it as a heroine.
5. That Last Scene
We end on a suddenly cool Annette Hargrove behind the wheel of Sebastian’s beloved Jaguar Roadster. She puts on his sunglasses (in slow-motion?!) and drives across the bridge as a satisfying smile creeps across her lips. I’d declare her behavior as triumphant, save for the fact that, you know, her love just died in the street while trying to save her from getting hit by a car. How perfect is that closing shot? Put it this way: Witherspoon motors from Manhattan to California in two seconds — I’ve lived in New York City since 1998 and have yet to see a single mountain — and the location inconsistency goof is no biggie! Besides, 20 years later, admit it: You’ve never heard “Bittersweet Symphony” the same way again.
Cruel Intentions is available to purchase on Amazon Prime, Vudu and YouTube. Plus, it’s returning to theaters for the anniversary. You can buy tickets here!
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