To celebrate its 20th anniversary, Cruel Intentions, written and directed by Roger Kumble, returned to theaters for a limited run. The film’s re-release ends this week, but it could always make another comeback into the pop culture zeitgeist.

various stills and BTS from the 199 movie Cruel Intentions
Credit: Courtesy of Roger Kumble and Sony

After all, other Intentions have been made before. Hollywood revisited Manchester Prep with a prequel series-turned-TV movie (2001’s Cruel Intentions 2, starring Amy Adams — yes, that Amy Adams — as Kathryn instead of Sarah Michelle Gellar), then a sequel that followed Kathryn’s cousin (2004’s Cruel Intentions 3), and finally an unaired NBC pilot set 17 years after the original that followed Sebastian (Ryan Phillippe) and Annette’s (Reese Witherspoon) son. More recently, a jukebox musical — Cruel Intentions: The ’90s Musical — brought the story to life on stage; the production, jam-packed with the decade’s earworms, is now on a national tour.

Credit: Everett

In other words, Cruel Intentions could continue to inspire new treatments. “I’m sure there could be some new iteration of it with new people,” Witherspoon tells EW in the film’s exclusive oral history. “It’s a piece of classic literature about how people manipulate each other. It’s just about somebody who’s imaginative, like Roger, coming up with a new idea around it.”

Sean Patrick Thomas, who played Ronald, agrees. “It’s harder to shock people now than it would have been back then, so I think Roger would have to do it again,” he explains. “What made [Cruel] work was Roger Kumble’s vision.”

And Kumble has had ideas, to be sure. He’s tried twice to expand the world of Cruel Intentions: first, by writing and directing the series that had to be re-cut and turned into Cruel Intentions 2, then by writing and directing the unaired NBC pilot, which modernized the story and drew Gellar back to reprise her role. “One of these days, I think we should just put that pilot out,” Kumble says. “I’m so proud of it.”

But, he admits, coming up with something new after those previous attempts would require more than just the right idea; it’d also require the right timing. Biting, high-society teen dramas have scored with audiences since the days of Cruel — Kumble cites Gossip Girl and Pretty Little Liars as worthy successors — but “it’s mutated,” he says. “There are moments [when audiences welcome a comeback]… but after 30 years in this business, I tend to try not to wallow.”

Much of the cast feels the same way. Witherspoon says she would have to revisit Annette and “see if she’s still a character I relate to” before considering playing the role again, while Phillippe explains he’d rather dive into a project similar in tone than to take on Sebastian once more. “I would like to do something like [Cruel], certainly, but when you talk about the actual role, it would be hard to manufacture something that would feel right,” he says. “You’d really be asking the audience to ignore the original.”

Even Gellar, who reprised Kathryn in the NBC pilot, echoes that assessment. “[The pilot] was more about timing,” she concedes. “[Cruel] was just such a perfect combination of so many things. You can’t recreate it.” Adds Selma Blair, who played Cecile: “It would be almost sad to revisit it. I’m just happy I have my beloved friend [Sarah], and a great movie I can watch on a Sunday night.”

That said, one cast member does find the idea of returning to his role intriguing. “It would be interesting to see who that man is 20 years later,” says Joshua Jackson, who played Sebastian’s best friend, Blaine. Jackson guesses Blaine would likely have settled down with a partner and started a family, but because of Blaine’s upbringing, they’d have “a little Stepford dynamic outside the city.” Sounds appropriately bittersweet.

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