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The nice thing about adapting 18th Century novels to the screen is that you don’t have to pay for the underlying literary rights.

That could be why so many films have been based on Pierre Choderlos de Laclos’ 1782 classic “Les Liaisons Dangereuses” — including Roger Vadim’s 1959 French language LES LIAISONS DANGEREUSES, starring Jeanne Moreau, Gérard Philipe & Annette Stroyberg; Stephen Frears’ 1988 DANGEROUS LIASIONS, a best picture Oscar nominee, starring Glenn Close, John Malkovich & Michelle Pfeiffer; and Milos Forman’s 1989 VALMONT, starring Colin Firth, Annette Bening & Meg Tilly.

Another de Laclos adaptation that easily slips under the radar is writer-director Roger Kumble’s 1999 teen romantic drama CRUEL INTENTIONS, starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon & Selma Blair. This modern version of the book is set in the world of rich Manhattan prep school teens.

Made by producer Neil Moritz’s Original Film, CRUEL was acquired by Columbia Pictures, which opened it March 5, 1999. Produced on a low budget six week shoot for $10.5M, it did $76.3M worldwide, a good number at the time. Its success sparked a 2001 video prequel, a 2004 video sequel, a 2015 musical staged in L.A. & New York & a 2024 TV series.

Moritz had a big hit two years before CRUEL with the horror mystery I KNOW WHAT YOU DID LAST SUMMER, starring Gellar & Phillippe. Not surprisingly, they were his first casting choices for CRUEL. The film’s original title was “Cruel Inventions,” but when research screening audiences said that sounded like a sci-fi picture, “Inventions” quickly became “Intentions.”

Gellar plays Kathryn Merteuil, a popular upperclassman at an elite school  who’s promised to help a naive freshman, Cecile Caldwell (Selma Blair). Kumble had a tough time getting Christine Baranski to play Cecile’s mom. She finally agreed because her daughters loved Gellar’s BUFFY THE VAMPIRE SLAYER and were excited that their mom would now be working with its star.

Columbia wanted Katie Holmes to play the innocent Annette, who by Phillippe’s character, Sebastian Valmont, seduces. But Kumble felt she didn’t have enough character strength for the role and asked Phillippe  about getting his real life girlfriend, Witherspoon, to play Annette.

They got her to say yes, according to Kumble, by taking her to dinner — as he put it — “to get her drunk — and we ended up getting drunk. I literally got down on my knees and begged her, ‘Please, it’ll (take just) 15 days and you’ll be great!’”

Casting Witherspoon & Phillippe had Hollywood gossips claiming they really were having sex in one of the film’s steamiest scenes. Real looking or not, Kumble insisted the sex was simulated and that, in fact, they weren’t even fully naked in that scene that only showed them from the waist up.