14 Facts About 'Cruel Intentions'

In Cruel Intentions, high school students and step-siblings Sebastian (Ryan Phillippe) and Kathryn (Sarah Michelle Gellar) wager on Sebastian's ability to seduce Annette (Reese Witherspoon), the headmaster's daughter who penned an article for Seventeen magazine titled "Why I Plan to Wait," about why she was choosing to save herself for marriage.

The 1999 film has maintained its popularity over the years. Despite a produced prequel series being re-edited into a direct-to-video sequel in 2000, NBC is currently working on a Cruel Intentions TV series, with Gellar reprising her role as Kathryn. Here are some facts about the movie to read before we toast to my triumph.

1. THE WRITER/DIRECTOR WAS INSPIRED BY WELCOME TO THE DOLLHOUSE.

Writer/director Roger Kumble saw Welcome to the Dollhouse (1995) and felt he had never seen anything like it—"so dark," "fu**ed up high school." It quickly led him to the thought of doing an update of Dangerous Liaisons, but set in high school. The day his 1997 play d girl, starring David Schwimmer, closed, Kumble went to Mexico and wrote Cruel Intentions in 12 days.

2. IT'S THE FOURTH SCREEN ADAPTATION OF LES LIAISONS DANGEREUSES.

The Pierre Choderlos de Laclos novel was first published in 1782. In 1959, Roger Vadim adapted the film for the screen using its original title. In 1988, Stephen Frears made Dangerous Liaisons with John Malkovich, Glenn Close, Michelle Pfeiffer, and Uma Thurman, which won three of its seven Oscar nominations. The following year, Miloš Forman made Valmont with Colin Firth and Annette Bening.

3. THE DIRECTOR BEGGED REESE WITHERSPOON TO PLAY ANNETTE.

Columbia Pictures wanted Katie Holmes to play Annette; Kumble didn't think she had enough strength of character for the role. Phillippe was already signed on as Sebastian when Kumble asked about his girlfriend, Reese Witherspoon. "So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk," Kumble revealed in 2014. "And I literally got down on my knees and begged her: 'Please, it'll be 15 days, you'll be great.'" Witherspoon agreed.

4. SELMA BLAIR WENT INTO HER AUDITION IN CHARACTER.

For legal reasons, Kumble had to ask all of the actors auditioning for Cecile how old they were, because of a graphic sex scene between the character and Sebastian in the movie. "So we were bringing in all these people," he recalled to Cosmopolitan, "and they were all good, but I remember Selma came in and I said, 'How old are you?' And she goes 'How old are you?' And she was so obnoxious and I couldn't get it out of my head." At 26 years old, Blair was the oldest high schooler in the movie.

5. THE ORIGINAL TITLE WAS CRUEL INVENTIONS.

In February, Gellar posted a photo dating back to the 1998 Cruel Intentions's "kick off dinner." In the caption, she wrote that the original title of the movie was actually Cruel Inventions.

6. THE PRODUCTION DESIGNER USED MOSTLY DARK COLORS ON PURPOSE.

Jon Gary Steele had it so that all of the locations they were permitted to paint were painted in dark colors. "I see the movie as very much a tragedy," Steele said in the film's production notes. "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."

7. WITHERSPOON WAS PURPOSELY CLOTHED IN LIGHT COLORS.

"I remember we wanted her in all white in contrast to Ryan’s all black, and when he gets hit by a car and sees her it’s almost as if she is an angel," said costume designer Denise Wingate.

8. WHEN WITHERSPOON SLAPPED PHILLIPPE, IT WASN'T SCRIPTED.

"At one point I was improvising off-camera for Reese," Phillippe told The Morning Call in 1999. "I guess I said some pretty mean things, so she came over and slapped me. Roger loved it so much he incorporated it into the scene. So basically I got slapped around for a couple of hours." Witherspoon and Phillippe got married three months after the release of Cruel Intentions and had two children together.

9. WITHERSPOON MADE PHILLIPPE VOMIT.

"Reese and I had a fight scene where we had to say horrible things to each other for four straight hours. After it was all over, I went outside and literally threw up," Phillippe admitted. "It was so emotionally punishing for me."

10. A PORN STAR CAUSED PROBLEMS ON SET.

Wanting to avoid an awkward situation with an actress having second thoughts about appearing nude in front of the camera, Kumble hired Alisha Klass, whom he considered "the biggest star in adult films in the late '90s," to play a naked cheerleader in the background of a scene where Sebastian is on the phone with Annette. But Klass' lack of attire created an awkward situation anyway. "The women on set have a problem," Wingate informed Kumble. "Your actor's at catering and she's wearing just a fishnet whatever, body skirt, and is basically flashing all of us." Klass' scene was eventually cut.

“I remember at the last minute deciding to put Selma in a red hooded sweatshirt so when she is leaving to go see Sebastian she looked like a contemporary Little Red Riding Hood going to see the Big Bad Wolf," Wingate told Dazed.

12. THE VISIBLE SALIVA IN THE KATHRYN/CECILE KISS WAS A "HAPPY ACCIDENT."

Gellar and Blair were not meant to produce the iconic spittle, but after someone on set they had to do the scene again, cinematographer Theo van de Sande proclaimed it was "beautiful."

13. THE SMASHING PUMPKINS SAID NO TO THE MOVIE.

The sex scene was eventually scored to "Colorblind" by The Counting Crows. Kumble wanted The Smashing Pumpkins song "To Sheila" for it, but singer/guitarist Billy Corgan turned them down.

14. THERE WAS A SEQUEL FEATURING AMY ADAMS.

The straight-to-video Cruel Intentions 2 was a reworking of Manchester Prep, a prequel series meant for Fox that never made it to TV despite three episodes being produced. Amy Adams portrayed a younger Kathryn. Cruel Intentions 3 (2004) took place in college with new characters, including Kathryn's cousin Cassidy.