It’s summer break, and Kathryn has been dumped by her beau, Court Reynolds, for the innocent Cecile. Desperate to get even, Kathryn challenges Sebastian to ruin Cecile by deflowering her and turning her into a tramp—thus humiliating Court by delivering Cecile to him as damaged goods. Sebastian has pretty much ‘had’ all of the girls in New York City up to this point, and he’s gotten a bit bored of it all. Though this is too easy a conquest for him, he obliges.

He sets his sights on a greater challenge—the new headmaster’s daughter, Annette, who recently wrote an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. Sebastian bets Kathryn that he can seduce the chaste and pristine Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled biblical pleasure, something he’s wanted since their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat.

Cruel Intentions is directed by Roger Kumble from a screenplay by Kumble, produced by Neal H. Moritz, executive produced by Michael Fottrell and co-produced by Heather Zeegen. Co-executive producers are William Tyrer, Bruce Mellon and Chris J. Ball. The cast is led by Sarah Michelle Gellar (Buffy the Vampire Slayer) as Kathryn Merteuil; Ryan Phillippe (54) as Sebastian Valmont; Reese Witherspoon (Pleasantville) as Annette Hargrove; Selma Blair (Zoe, Duncan, Jack & Jane) as Cecile Caldwell and Sean Patrick Thomas (Can’t Hardly Wait) as Ronald Clifford, with appearances by Louise Fletcher (One Flew Over the Cuckoo’s Nest) as Aunt Helen; Swoosie Kurtz (Dangerous Liaisons) as Dr. Greenbaum; Christine Baranski (Bulworth) as Mrs. Caldwell; Eric Mabius (Welcome to the Dollhouse) as Greg McConnell and Joshua Jackson (Dawson’s Creek) as Blaine Tuttle.

Rounding out the production team are director of photography Theo Van De Sande, A.S.C., production designer Jon Gary Steele, costume designer Denise Wingate and editor Jeff Freeman, A.C.E.

Director Roger Kumble had always been a fan of the original novel and had closely observed its previous incarnations on stage and screen. "I’ve always thought this novel was timeless and could be remade for a younger audience," he says. "Kids are vicious in high school, and when I re-read the novel about two and a half years ago, I realized how much high school kids act like the characters in the novel. So a different slant in making this movie would be to set it in the world of high school."

Although Kumble had written for the screen, he had not directed a feature film—and if he wrote this film, he very much wanted to direct. His successful theatrical productions—

Pay or Play starring Jonathan Silverman and Dana Ashbrook and d-girl starring David Schwimmer—had prepared him for directing his first feature film, but Kumble knew that it would be a fight to get a major studio to allow him to direct. "I planned on writing a really vicious, low-budget update of Dangerous Liaisons, and then going out and raising a million dollars and directing it," he says. "I had no idea it would turn out the way it did."

Co-producer Heather Zeegen had worked with Kumble in the past and admired his writing. She knew he was working on a modern-day adaptation with younger characters and thought it would be something Original Film might want to produce, having had success with

I Know What You Did Last Summer. "We were able to capture that youth market so well with Summer," she says. "I knew Neal would really spark to it."

At the time, Moritz was spearheading the comeback of youth films. His I Know What You Did Last Summer met with huge boxoffice success and he was in pre-production for the sequel. The third, Urban Legend, was ready to go and his much anticipated The Rat Pack had just wrapped. As soon as he read the script and saw how strong the material was, he immediately knew who he wanted for the two leads. "I had worked with Ryan Phillippe and Sarah Michelle Gellar on Summer and I knew they’d be perfect for the roles of Sebastian and Kathryn," says Moritz.

"It’s a rare situation in Hollywood, where you have ability to basically pick who you want for your roles. There are a slate of youth films being made right now, and it’s a very competitive market for this talent," he continues. "And when you’re lucky enough to have a piece of material like this, which all the young actors loved, you’re sitting in a position where you really get to find the best people. Ryan and Sarah are two of the most incredibly talented young actors in the business and I was dying to have them in the movie, even though every studio wanted them for their other movies."

Both Phillippe and Gellar recognized the script as something special—a real standout among the rest of the scripts sent to them. "When I read it I was immediately frightened and challenged and intensely interested all at once," says Phillippe, who knew immediately that if there was an opportunity to play Sebastian Valmont, he had to seize it. "Valmont has been played by some great actors, so I knew that it was a tall order," he continues. "But the script was so smart, funny, sharp and angry that I found it fascinating. There was no question that if I had the chance, I would be part of it."

For Phillippe, the chance to work on a film that was so character intensive was what attracted him. "This script is all about dialogue," he says. "There is no one chasing you with a hook, no explosions and no car chases. It’s all about relationships and their complexities and how you work within those confines, how they feed off of each other and push each other... it’s theatrical in that sense and more like a play. That, for me, is what is most appealing about acting in general."

The re-creation of the classic Valmont into a modern-day character presented Phillippe with many challenges. "To make it what it classically has been, I had to separate the layers of the character and each storyline and make the individual unique in his levels," says Phillippe. "Sebastian Valmont is a different person with each character with whom he comes into contact throughout the film. The Sebastian who spars with Kathryn is quite different from Sebastian the seducer when he deals with Cecile, and Sebastian the lover as he woos Annette. In each and every scene and with each and every actor and actress that I play opposite in the film, the character changes. So I had to develop those personalities for Sebastian. There is a fair amount of psychosis involved. Sebastian is so incredibly mean and so incredibly arrogant... yet he’s not. It’s put on. It’s make believe. But the audience has to weave their way through their experiences with him to find out what is real and what’s not."

It’s Sebastian’s surprising feelings for the new girl in town which sets him off kilter. Annette Hargrove is unlike any girl he’s met before. "She’s as smart as she is beautiful," he explains. "She’s funny, and she doesn’t take his antagonisms and that sort of thing. She gives it right back to him as much as he doesn’t want it. As much as he tries to resist it, he can’t help but be enchanted by her and want her, and he ends up falling in love with her and there is nothing he can do about it. He didn’t expect it and wasn’t looking for it. He didn’t want it, but it happens and he can’t lie to himself. And he bites it until he can’t any longer."

For Phillippe, the chance to work with Neal H. Moritz again, with whom he had worked on I Know What You Did Last Summer, brought a certain level of comfort. And it was the casting of Summer alumna Sarah Michelle Gellar in the role of Kathryn Merteuil to complement his Valmont that made the experience even more inviting.

"Ryan is the reason I’ve been able to do what I think has been my best work so far," says Gellar of her co-star. "He’s been able to get it out of me. He’s the most amazing young actor." The chance to portray the famously wicked character was a refreshing idea for Gellar. "It’s so different than what I normally do with Buffy,’" she says. "It was such a stretch, and as an actor, of course that’s what you want. It was the best written script, perhaps the best dialogue, for somebody of my age that I’ve seen in such a long time. It was the first script I read to consider on my break from ‘Buffy,’ and I wanted to commit right away. Everyone kept saying ‘no, Sarah, read other options’ and I said ‘I will tell you right now, there is nothing that I will read that I want to do more than this project.’ And I was right."

The chance to portray a witty, evil and, most importantly, intelligent character was what attracted Gellar to the role. "It’s wonderful to see characters who are aimed at people our age and who give the audience credit for being intelligent," she says. "These characters don’t talk down to young audiences, and that was important to me."

In the re-creation of Kathryn, Gellar made a few interesting choices. "I’ve tried, with my interpretations, not to mimic Glenn Close’s Marquise de Merteuil," she says. "That would be so easy since she did such a wonderful job. But the Marquise de Merteuil had a colder veneer. She hid her emotions. People weren’t as ‘out there’ as they are now. We can say more things than we were able to during the 18th century, and we can show more emotion. That was a great thing to be able to do—show emotion and not hide behind wigs, corsets and huge costumes. We were able to use our bodies, which makes a very big difference when telling a story like this. Kathryn needed to be able to use her body because her sexuality is all she thinks she has."

With the two leads in place, Reese Witherspoon was brought on to play the chaste Annette Hargrove, the updated version of Mme. De Tourvel and object of Valmont’s desires. The script appealed to her sense of humor and presented several challenges for the actress. "One of the hardest things for me about Annette was to find a modern way to make a teenager a virgin," says Witherspoon. "Not to say that all teenagers are sex-starved people, but it was actually difficult to find a reason that wasn’t self-righteous or obnoxious." In working with director Roger Kumble, the two came up with something that they felt cut close to the heart. "Annette is not interested in having sex for anything but love, and she’s waiting for love," says Witherspoon. "I think that’s what is appealing to Sebastian as well."

The final peg of the foursome, Cecile, was the only role left to be filled. "Cecile is somewhat of the comic relief in this piece," explains Kumble. "She’s a brat who is turned into a slut by Kathryn and Sebastian, and now she’s such a brat about wanting sex all the time, it annoys them. I needed an actress who could be both innocent and sexy in the same moment." Newcomer Selma Blair was cast in the role. "It’s fun as a director to find someone who no one has seen before," adds Kumble. "Reese, Ryan and Sarah are already established actors and you have that joy as a director to find someone no one knows and hopefully turn them into somebody that everyone’s interested in. I think I found that with Selma." Producer Moritz agrees. "Watching Selma perform, watching her dailies, and watching the cut together scenes amazed me. She has that characteristic that when you watch her on screen, you want to watch her. To me, that’s what makes the difference between actors and stars—that when you see them on screen, you can’t take your eyes off of them. Selma has that quality."

"It was the first story that I had read that was so amazingly evil," says Blair. "Then I met Roger and I fell in love with his style of directing in the auditions, and I just knew I wanted to do this."

With the cast in order, executive producer Michael Fottrell and producer Neal H. Moritz put together a production team for the new director. "We knew Roger was prepared to direct since he had worked in theater," says Fottrell. "But we also knew that he needed a strong support team to get him through the picture." With the help and experience of a great cinematographer (Theo Van De Sande) and editor (Jeff Freeman) along with Fottrell and

Moritz, Kumble had the support he needed. "The three or four of us would talk him through things and get him over the little hurdles that he was tentative about on occasion," says Fottrell. "For example, using a crane or a camera move, or technical things relating to covering a scene in a certain manner. But as far as getting the performances out of the actors, he’s stellar."

"This is my seventh movie in a row with a first-time director," says Moritz. "I couldn’t be working with a more qualified, intelligent, enthusiastic director than Roger Kumble. He knows exactly what he wants."

"I wasn’t going to take a crash course in filmmaking for three weeks before I shot this," adds Kumble. "My producers just knew I needed a strong team. It’s like when you’re President of the United States. If you’ve got a great cabinet, you’ll have a good administration. If you get a lousy one, you’re in deep trouble."

With the cast in place, the filmmakers set out for the six-week shoot in Los Angeles and New York.

Even though Cruel Intentions is a modern-day piece, production designer Jon Gary Steele created an overall look for the film which paid homage to the original novel.

The interior sets of the Valmont townhouse, for example, which were built and shot in L.A., were given a French twist. "Most of the story takes place in modern-day New York, but when you walked into the Valmont townhouse, I wanted you to feel like you were walking into a Parisian ballroom," says Steele.

In order to create the dichotomy, Steele gave the walls, paintings and art a period feel and gave the furniture a more contemporary feel. "The furniture in the living room was very Louis XIV," he said. "We stripped the wood and reupholstered it in a much more modern fabric so the room didn’t feel totally period. Then we added bronze chairs and a bronze table. I didn’t want it to feel like only one piece of the film was period and everything else was modern-contemporary. I wanted the audience to feel like it was a period piece, but once they examined the room and noticed the detail, they would realize the contemporary additions.

"Because these people have blue-blood money and are very much world travelers, I put in a little bit of everything," he adds. "There are a lot of French buildings in New York. It’s not uncommon to find people like this now living in places like this."

When Steele and his crew set out to find what would become the exterior of the Valmont townhouse, they found a huge French chateau on 79th Street and 5th Avenue, which is now the Ukranian Institute of America. The chateau was built in 1898 and designed in limestone in the French Gothic style. Steele was surprised to find that the interior of the chateau was similar to the Valmont interior set he created in Los Angeles, right down to the similar moldings and comparable room dimensions.

His next step was to plan the bedrooms for Sebastian and Kathryn, which were more modern in design. "I designed Kathryn’s room with a very French flair, complete with a built-in French bed. I felt like she was this cold ‘ice princess,’ and so we painted the room in very cold colors of silver and blue and used crystals so everything feels cold around her. I always saw her as a very cold, calculating character, and I wanted to take that and make it hip and young."

For Sebastian’s room, Steele kept the colors in dark and rust tones, complementing Sebastian’s dark personality. "We shaded the colors on his walls from the bottom up, from the darkest to the lightest tones. It’s a very theatrical thing to do. I thought this whole family was very theater-like, and that’s why I made Kathryn’s bed the way it is and why Sebastian’s room is like the theater. I felt like they were actors acting out a play in their own lives."

Steele deliberately used dark colors throughout the entire film. "I see the movie as very much a tragedy. Since we were using a young cast, I didn’t want it to feel like a young, bright teen film, because it’s not. It’s very tragic; everyone basically loses. It’s all about manipulation and trying to get what they want out of life by using and abusing other people, and I found it very dark. So all of the colors that we could control and most of the locations that we could paint were painted darker colors."

In the Caldwell apartment, Steele’s use of art created a visual joke when played against a very serious scene. "I wanted to show the opposite of the Valmont home," he says. "They both have tons of money, but the Valmonts are blue-blood and the Caldwells are a bit nouveau riche. In one very poignant scene, Mrs. Caldwell is outraged because her daughter is having an affair with a black man and Mrs. Caldwell is very racist. Well, all around them in the background, African-American art is everywhere—on the walls, on the tables, statues etc."

Finally, Steele needed to find an estate to provide exteriors for Aunt Helen’s house. The estate was to be "very Americana." He found what he was looking for at Old Westbury Gardens in Long Island, N.Y. The stately three-story mansion with its elegant Charles II style and outstanding gardens on 150 acres is a magnificent example of the finest in period landscape design and architecture in America. The house and grounds were the country home to the family of financier and sportsman John Shaffer Phipps and his wife, Margarita Grace, and were designed for the Phippses in 1904 by English architect George A. Crawley. The manor house is composed of cherry-red brick from Virginia laid in a double-diamond pattern and cream-colored limestone from Indiana and features a glazed terra cotta cornice and a roof of thin stone slabs imported from Rutlandshire.