Long Island iced tea, please! Two decades after its premiere in 1999, Cruel Intentions still has fans talking about its scandalous story line — and dreamy lead Sebastian Valmont.
In the 90s cult classic, which is a teen version of the French film Dangerous Liaisons, Sebastian’s (Ryan Phillippe) sultry stepsister Kathryn Merteuil (Sarah Michelle Gellar) challenges him to “deflower” the new school headmaster’s daughter Annette Hargrove (Reese Witherspoon).
What Sebastian doesn’t expect is to fall in love with Annette and find himself broken after she learns the truth about the bet. In the end, Annette comes out on top besting Kathryn at her own game before riding off into the sunset. Sadly, Sebastian isn’t by her side — he sacrifices himself to save Annette — but she feels his presence while driving his beloved convertible as The Verve’s “Bittersweet Symphony” plays in the background.
“It makes me smile almost every time. No matter where I am,” Phillippe exclusively told Us Weekly in September 2021 of the iconic final scene playlist. “And there’s been a couple of times in my life where I’ve been, like, at a gas station or whatever. And I’ll suddenly hear the song from across the way. And then there’ll be a group of people waving to me. Like, they put the song on a purpose because they saw me there.”
The Big Sky actor, who got engaged to Witherspoon while filming the drama, added: “But to have to be associated with a song, there could be way worse songs to be associated with. You know, it’s a really great song still. And so when I hear those strings start up, it does, it still makes me happy. So it makes me smile.” (Phillippe and Witherspoon tied the knot in 1999 but called it quits seven years later.)
In addition to Sebastian and Annette’s twisted love story, Cruel Intentions highlighted the secret lives of a group of Upper East prep school students, including their sex lives, mischievous activities and raunchy extracurricular jaunts.
One of the most iconic scenes came when Kathryn teaches Cecile Caldwell (Selma Blair) how to kiss while using her as a ploy in her game. Plus, Cecile needs pointers to win over her music teacher (Sean Patrick Thomas).
“Selma’s a great kisser,” Gellar exclusively told Us in February 2021. “I mean, I’ll tell you, it’s just soft [lips]. She smells great.”
The Buffy the Vampire Slayer star confessed: “Kissing a girl on camera is way better because when you kiss a guy, all your makeup rubs off and then in between you have to get these touch-ups. But [when] it’s a girl it’s, like, you’re good to go.”
Looking back, the I Know What You Did Last Summer actress told Us she knew the film would be “iconic” but she didn’t know how successful it would become.
“Obviously, we knew people would be excited by it, but I read that script and I was so desperate to be a part of it,” Gellar added. “And I’ve loved it forever. I’ve seen every iteration, every Broadway version.”
Scroll down to see what the cast of Cruel Intentions has been up to since 1999:
