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Cruel Intentions (1999) Poster

Trivia

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The scene in which Annette slaps Sebastian was unscripted. Reese Witherspoon and Ryan Phillippe were so into their scene that she slapped him unexpectedly, and Phillippe's reaction is genuine. He was so into the scene that right after the director said cut, he went behind the set and threw up. The director left the scene in the final cut.
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Columbia Pictures wanted Katie Holmes to play Annette, but Roger Kumble didn't think she had enough strength of character for the role. Ryan 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.
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The movie was originally called Cruel Inventions, but test audiences thought that made it sound like a science fiction film, so the name changed before it was released.
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The final straw in snagging Christine Baranski, who only had to work three days, was that her daughters were big Buffy the Vampire Slayer (1996) fans and were giddy that she could work with Sarah Michelle Gellar.
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Ryan Phillippe recalled that after filming a fight scene with Reese Witherspoon where the two of them viciously insult each other, he felt so emotionally drained that he went outside and threw up after it was over.
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Selma Blair who plays the role of the young freshman Cecile is older than both Sarah Michelle Gellar and Ryan Phillippe by 5 and 3 years respectively.
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For legal reasons, Roger 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 remember Selma [Blair] 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."
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Despite previous reports, Reese Witherspoon was not pregnant during filming. The movie filmed from 9 June 1998 - 15 July 1998, and Witherspoon had her daughter Ava on 9 September 1999. A full year after filming the movie. She was, however, pregnant, when they did the press tours for the film.
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According to Costume Designer Denise Wingate, Reese Witherspoon was deliberately clothed in light colours in order to contrast with the dark colours of Ryan Phillippe.
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Neal H. Moritz, who had worked on I Know What You Did Last Summer (1997) help cast the film. His first choices were Ryan Phillippe and Sarah Michelle Gellar who also starred in Summer.
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The film was shot in a six week period.
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During the movie Ryan Phillippe and Reese Witherspoon were dating. The couple got married three months after the movie's release and had children together, but ended up divorcing in 2008.
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The kissing scene between Sarah Michelle Gellar and Selma Blair, ranked the film at #32 on Entertainment Weekly's "The 50 Sexiest Movies Ever" (issue #1023, November 28, 2008).
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An avid collector of antique books, Sarah Michelle Gellar herself owns an early edition of 'Les Liaisons Dangereuses'.
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According to Denise Wingate, Selma Blair's red hoody was supposed to invoke Little Red Riding Hood.
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Roger Kumble was inspired by Welcome to the Dollhouse (1995). He felt he had never seen anything like it-"so dark," "fucked up high school." It quickly led him to the thought of doing an update of Dangerous Liaisons, but set in high school.
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Roger Kumble initially wrote the script in 12 days.
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Neal H. Moritz contractually agreed to the film being rated R, and nothing less. Sony (the studio) agreed.
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During their kissing scene, Sarah Michelle Gellar and Selma Blair were not meant to produce the spittle, but after someone on set noticed, they had to do the scene again. Cinematographer Theo van de Sande proclaimed it was "beautiful."
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The Valmont townhouse interiors were built and shot on sound stages in Los Angeles while the exterior scenes were filmed in New York City.
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When Sebastian is handing Kathryn the Seventeen magazine to read, on the cover is Jennifer Love Hewitt, who previously starred with Sarah Michelle Gellar and Ryan Phillippe from I Know What You Did Last Summer (1997).
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Swoosie Kurtz also appeared in Dangerous Liaisons (1988) which, like this film, is based on the Choderlos de Laclos novel "Les liaisons dangereuses".
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When Kathryn exits the church at the end of the film a plaque to the left of the doorway says "Rosemond Chapel." Rosemond is the last name of Valmont's aunt in both Cruel Intentions and Dangerous Liaisons (1988).
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The sex scene was eventually scored to "Colourblind" by Counting Crows. Roger Kumble wanted the Smashing Pumpkins' song "To Sheila" for it, but singer/guitarist Billy Corgan turned them down.
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Although Sarah Michelle Gellar plays the older version of Kathryn while Amy Adams plays the younger version in the prequel Cruel Intentions 2 (2000), in real life Sarah Michelle Gellar is younger than Amy Adams by 3 years.
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Fred Norris, head writer and cast member of The Howard Stern Show (1987), has a small part, credited as the Meter Maid - Ryan Phillippe is a huge Howard Stern fan.
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Production designer Jon Gary Steele, had it so that all of the locations they were permitted to paint were painted in dark colours. "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."
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Reese Witherspoon (Annette) and Selma Blair (Cecile) both went on to star in 2001's Legally Blonde
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Porn star Alisha Klass appeared as a cheerleader, but her brief scene was cut. You can see a glimpse of her in the lower right hand part of the screen when Sebastian is talking to Annette on the phone.
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John Ottman's score was originally used during the trailer, however his score was rejected shortly before the film was released and was replaced by Ed Shearmur.
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Tara Reid and Joshua Jackson appeared together in Urban Legend (1998) the previous year.
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Cruel Intentions (1999) heavily influenced the 2002 story-line in the long-running British soap opera Coronation Street (1960) which Tracy Barlow (Kate Ford) makes a bet with Bev Unwin (Susie Blake) to sleep with Roy Cropper (David Neilson).
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The German dubbed version of the film is called "Eiskalte Engel" - ice cold angels.
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Spoilers 

The trivia items below may give away important plot points.

One version of Roger Kumble's screenplay had an ending where Annette, instead of publishing the journal and crushing Kathryn, keeps it to herself and announces her cruel intentions to play games on Kathryn under the threat of revealing the contents.
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Toward the end of the film when Kathryn tells Ronald that Sebastian had hit her, the actual scene of Sebastian striking her was filmed, but it was deleted because the dialogue from Sebastian during this part didn't fit his character, and the writers decided to let the audience decide for themselves whether he actually did hit Katherine or she made it up.
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After her public humiliation, Kathryn Merteuil's cross gets pulled open and her cocaine falls out, referencing the scene in Dangerous Liaisons (1988) in which the similarly disgraced Marquise de Merteuil (Glenn Close) sweeps a cloud of white powder off her dressing table.
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The scene which takes place after Cecile's 'first time'... she's eating cherries. In American culture losing your virginity is often referred to having "your cherry popped."
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