Things You Might Not Know About Cruel Intentions

Cruel Intentions was a romantic teen drama that was released in 1999 and starred Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. Although the film received mixed reviews from critics, it was a commercial success, earning $75.9 million on a $10.5 million budget. To this day, the movie is beloved by fans, which is why we dug up these 12 fascinating facts that you might not know about the popular ‘90s flick:

12. Cruel Inventions

The original title of the film was Cruel Inventions. Sarah Michelle Gellar revealed this on Instagram in 2016. “#throwbackthursday ok one last one because I was feeling nostalgic – and yes #CruelInventions was the original tittle. This pic was 1998 at our kick off dinner #cruelintentions #Crueltv #kathrynmerteuil,” she wrote. The title was reportedly changed because “Cruel Inventions” didn’t test well with audiences and people thought it sounded more like a science fiction film instead of a drama.

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11. Annette’s Slap

The scene where Annette (Witherspoon) slaps Sebastian (Phillippe) wasn’t scripted. “At one point I was improvising off-camera for Reese. I guess I said some pretty mean things, so she came over and slapped me. (Director) Roger (Kumble) loved it so much he incorporated it into the scene. So basically I got slapped around for a couple of hours,” Phillippe told The Morning Call.

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10. The Studio Wanted Katie Holmes to Play Annette

The studio initially wanted Katie Holmes for the Annette part, but director Roger Kumble thought the role “needed someone with a little more strength of character.” Phillippe was already signed on to the part of Sebastian, so Kumble became interested in hiring his girlfriend at the time, Witherspoon. “So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk,” Kumble said. “And I literally got down on my knees and begged her: ‘Please, it’ll be 15 days, you’ll be great.’ And Reese was like, ‘I’ll do it. But we need to work on the character.’ I’m like, ‘Anything, anything, anything.’” Together they strengthened Annette’s character, so that she wasn’t such a “doormat.”

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9. Inspired by a Book

Cruel Intentions was inspired by the movie Welcome to the Dollhouse. The director Roger Kumble had recently seen it and felt as though he hadn’t seen such a dark high school flick. “I’d just seen Todd Solondz’s Welcome to the Dollhouse, and I was like, Wow … f–ked up high school. Never seen this. It was so dark. And it was one of those moments when you’re just walking across the street, and the idea popped into my head to do Dangerous Liaisons set in high school. And I mulled it over for a year,” Krumble said. “Then I put a play up in 1997 called d girl and I got David Schwimmer to be in it, at the height of Friends. And that was a game-changer for me. It was a pretty dark play. It was about a screenwriter who’s just looking to seduce this innocent d-girl [short for development girl, a person in film production who scouts potential movie ideas]. I put that up and it was a hit out in LA. So I had some heat, and I didn’t want to lose it. Literally, the day the play went down I went to Mexico and I wrote Cruel Intentions in 12 days.”

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8. Phillippe Became Physically Ill after a Fight Scene

After filming one of his fight scenes with Witherspoon, which was particularly vicious, Phillippe actually became physically ill! “Reese and I had a fight scene where we had to say horrible things to each other for four straight hours,” he told The Morning Call. “After it was all over, I went outside and literally threw up. It was so emotionally punishing for me.”

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7. Selma Blair’s Audition

When auditioning actresses for the part of Cecile, which went to Selma Blair, director Roger Kumble was required (for legal reasons) to ask how old they were. One thing that made Blair stand out was the attitude she gave Kumble for asking her that question. “So we were bringing in all these people and they were all good, but I remember Selma came in and I said, ‘How old are you?’ And she goes [in Cecile’s bratty voice] ‘How old are you?’ And she was so obnoxious and I couldn’t get it out of my head. She came into the audition as the character and didn’t show me that there was Selma; I said, ‘This is the person,’” he told Cosmopolitan.

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6. Also Inspired by a Book  

Another inspiration for Cruel Intentions was the 18th novel Les Liaisons dangereuses by Choderlos de Laclos, which was about the Marquise de Merteuil and the Vicomte de Valmont, two ex-lovers who use seduction as a weapon to socially control and exploit others. Director Roger Kumble wanted to adapt it for the modern day with wealthy teenagers in a fancy Manhattan private school setting.

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5. Casting Sebastian and Kathryn

Director Roger Kumble cast Phillippe and Gellar after talking to Neal Moritz, who produced the ‘90s horror flick I Know What You Did Last Summer. “It was really a series of fortunate breaks. I got it into the hands of Moritz, and he had just made I Know What You Did Last Summer, [which starred Phillippe and Gellar]. He showed me it early on and said, ‘Here are two actors,’” Kumble told The Telegraph. “I knew Sarah from [Buffy], but I didn’t know Ryan’s work. I was also looking at Jonathan Rhys Meyers at the time, because a lot of young Hollywood back then wanted to do it. But I kind of responded to both of them. Sarah was dying to break out from Buffy, and Ryan just had that kind of Valmont air about him.”

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4. Annette Was Dressed in Light Colors on Purpose

The costume designer Denise Wingate chose light colors for Annette’s wardrobe on purpose because she wanted to contrast the character with Sebastian who was dressed in dark colors throughout the film. “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.”

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3. Portraying Kathryn as Unsympathetic

It was Gellar’s decision to dye her hair to play Kathryn. She didn’t want to look anything like Buffy, and she also rejected efforts by the director to make her character more sympathetic. “We had long talks about her history,” Gellar told Premiere Magazine in 1999. “Roger used to always say, ‘Don’t you think that she was abused?’ And I’d say, ‘No, I think she had a perfect upbringing. I think her mother adored her and her father sent her amazing gifts. She just wanted more.”

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2. Cecile’s Red Sweater

Denise Wingate, the costume designer on the film’s set, decided to put Cecile (Blair) in a red sweatshirt for a scene with Sebastian to give her a Little Red Riding Hood look. “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. A lot of subliminal things go into my selection of costumes that usually nobody notices,” she said.

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1. Cruel Intentions 2 Starred Amy Adams

After the success of Cruel Intentions, Fox Television approached Roger Kumble about developing a prequel series to the movie that came to be called “Manchester Prep,” which starred none other than Oscar-nominated actress Amy Adams. Unfortunately, the material was way too sexually charged for television and the show was abandoned, so Kumble recut the three episodes that were filmed and turned into a 90-minute straight-to-video release called Cruel Intentions 2.