20 Years Later, The Cast Of “Cruel Intentions” Dish On How They Knew It Was Going To Be A Classic

Twenty years after the 1999 film Cruel Intentions hit theaters, one of its stars, Sarah Michelle Gellar, told Entertainment Weekly her representatives “thought it was a terrible idea” for her to get involved with the dark, sexualized dramedy given that she was so well-known for her role on Buffy the Vampire Slayer.

“They were like, ‘You’re Buffy! People have this great idea of you — why shatter it?’ I was like, ‘That’s the point!'”

Cruel Intentions, directed by Roger Kumble, is about a group of rich teenagers who attend a prep school in New York City. The teens, led by Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair, get into their fair share of trouble involving sex, drugs, and other dark shenanigans that were groundbreaking in the genre. But for the cast, and clearly audiences, it found a place in cinematic history.

There was something about this script that just felt like something that could last,” Phillippe, who played Sebastian, said. “The first time I finished reading it, I was like, ‘There’s no way they can make this.'”

Joshua Jackson, who played Blaine, said roles for teenagers at the time “were written very two-dimensionally: You were the jock or the nerd or the hot one.” That is, until Cruel Intentions.

“I was a precocious 19- or 20-year-old who expected roles to be intelligent and stupid and bad and funny and over-the-top,” he added. “[This] elevated the material.”

The first scene Jackson shot for the movie involved him giving a blow job, but he said he wanted to make sure he brought authenticity to the role because of what it meant for LGBT representation onscreen.

You didn’t see a lot of gay characters, period, but [especially] gay characters that weren’t caricatures,” Jackson said. “So I wanted to make sure that, even with dialogue that was beautifully over-the-top, he still felt like a real person.”

As for how the iconic cast came together, a smaller pool of Hollywood talent at the time made for easier connections.

“If I tried to make a list of teenage actors now, it’d be 30 pages long. There are so many shows — the kids on Netflix, the kids on The CW — it’s just a bigger universe,” co–casting director Anne McCarthy said.

Her counterpart, Mary Vernieu, told EW that in all the big teen movies at the time — like I Know What You Did Last Summer, Can’t Hardly Wait, etc. — “it was all the same group of kids coming up.”

In fact, they had originally wanted the late Brittany Murphy to play Cecile, the character Blair ended up getting cast in.

“She was coming off of Clueless, but she ultimately ended up not being available, so then we went in looking for someone, and we found Selma, who was a discovery for us,” Vernieu said. “She really brought something so special to Cecile.”

Witherspoon, who played Annette, was dating Phillippe at the time and said that she was coerced into accepting the role after being taken out to dinner by her then-boyfriend and the filmmakers. Everyone remembers her being reluctant to take on the part, but she worked with filmmakers to adjust Annette’s character.

“I remember finding Annette too demure and too much of a woman influenced by a guy’s manipulations,” Witherspoon said of her character. “I was starting what I guess became my bigger mission in life — of questioning why women were written certain ways on film.”