20 Crazy Details Behind The Making Of Cruel Intentions

Cruel Intentions DVD Cover

Love, betrayal, power, privilege, and envy are just some of the many themes found throughout the 1999 hit movie Cruel Intentions. Serving as another film adaptation of the French novel Dangerous Liaisons, the movie’s setting reflected a more modern take on the tale.

Set in the rich prep school in New York City, the lead roles for the film were converted to a step-sibling team. The Marquise de Merteuil became Kathryn Merteuil, and the Viscomte de Valmont transformed into her stepbrother, Sebastian Valmont. Their manipulation and deception control the actions of the film as they plan to execute on their devious plans. In the middle of their scheming are the love lives of both Annette Hargrove and Cecile Caldwell.

With their wager in place, the two villains set a course to win the grand prizes at stake: Sebastian’s car and Kathryn’s “forbidden love."  The film pushed the envelope with numerous scenes of lost innocence, carnal manipulations, substance abuse ,and other deviant behaviors that no high schooler should be partaking in. Audiences fell for the wild behaviors of the main leads and the eventual revenge of the innocent bystanders. The film went on to become a fan favorite of 1999, picking up a few fan-based movie awards along the way.

Even today, the mere mention of Cruel Intentions brings with it memories of its outrageous moments (including one unforgettable kiss). In this article, we will uncover the truth behind the many outrageous scenes and how the various spinoffs it has inspired.

Here are 20 Crazy Details Behind The Making Of Cruel Intentions.

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David Schwimmer as Ross Geller in Friends
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20 David Schwimmer Helped the movie get made

David Schwimmer as Ross Geller in Friends

Cruel Intentions director Roger Kumble got his start working as a playwright and director in the early 1990s. Still looking to get his foot in the door of Hollywood, he finally gained some attention thanks to his project the Friends star.

In an interview with Cosmopolitan, he revealed, “…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.” Thanks to not only the good reviews of the play but the lead’s star power as well, Kumble got enough recognition to try for a big screen movie finally.

After the conclusion of the play’s run, he traveled down to Mexico to concentrate on the Cruel Intentions script, completing it in only twelve days.

19 The Original Title of the Film was Cruel Inventions

Cruel Intentions Original title

Despite the modern setting, the general plot of remained true to the source material of Dangerous Liaisons. The plot included various levels of deception, trickery, manipulation, and cunning schemes all originating from a bet between the two step-siblings.

Considering their selfishness toward others’ feelings, the title of the film perfectly captured the theme of the movie. However, thanks to Cruel Intentions lead actress Sarah Michelle Gellar, we learned the original title of the film was much less intimidating.

In an Instagram post on February 25, 2016, Gellar reminisced about the movie with a picture of the cast from 1998. In the caption, she shared, “yes #CruelInventions was the original tittle (sic)”.

18 The "I Know What You Did Last Summer" reunion

I Know What You Did Last Summer Poster

After completing the script for the film, Kumble began his search for the cast. Lacking a studio to back the film, he began the process of producing the film independently. Though he originally thought of actor Jonathan Rhys Meyers for the film, a fellow director led him to cast Ryan Phillippe and Sarah Michelle Gellar as the leads instead. Why? Because of the successful horror movie, I Know What You Did Last Summer.

Kumble explained, “I met Neal Moritz who's now like, Neal Moritz [producer of Fast & Furious, 21 Jump Street, I Am Legend, and more] through this person who was working for him at the time. She brought him the script and he was like, 'I just made this movie, I Know What You Did Last Summer, and there are these two actors in it; you really should meet them.'” It turned out to be the perfect casting.

17 The Movie Led To A Prequel and a Sequel

Between the edgy material, diverse cast, and unforgettable soundtrack, Cruel Intentions went on to be one of the most talked-about movies of 1999. Thanks to its popularity, several spin-off movies have been made as a continuation of the story.

The first movie, Cruel Intentions 2, served as a prequel to the series, and starred Amy Adams as Kathryn Merteuil.

Although the story was originally conceived as a TV show called Manchester Prep back in 1999, the show got canceled before it even aired. The adapted TV movie focused on Sebastian and Kathryn meeting for the first time.

Cruel Intentions 3 held no connections to the prior films other than the main character being Kathryn’s cousin.

Both films were direct-to-video released and never fared as well as the original.

16 Sarah Michelle Gellar Dyed Her Hair to Shed Her Buffy Image

Sarah Michelle Gellar’s popularity skyrocketed when she took on the lead role in Buffy the Vampire Slayer. For seven seasons, audiences were enthralled with the character, helping to make the show a cult favorite.

Benefitting from the show’s immense popularity, Gellar continued to expand her acting career on the big screen. However, she found it difficult to separate her role as Buffy and her potential movie roles. After accepting the role in Cruel Intentions, Gellar decided to dye her hair to help shed her Buffy image.

She also wanted to make the character as vicious as possible. 

In an interview with Premiere Magazine, she shared her thoughts on the character Kathryn: “…I think she had a perfect upbringing. I think her mother adored her and her father sent her amazing gifts. She just wanted more.”

15 Annette slapping Sebastian wasn't planned

Annette Sebastian Break Up in Cruel Intentions

The relationship between Sebastian and Annette may have started off shaky, but the trust between the two gradually grew. As Annette began to trust him more, she eventually succumbs to her feelings for him and gave herself to him. Along the way, however, he ended up falling in love with her and eventually lost interest in his prize for achieving his goal (aka Kathryn).

His stepsister made him feel guilty, and he decided to break off their relationship. During the heated argument, a broken-hearted Annette lashed out against Sebastian and promptly slapped him across the face.

In reality, the slap was not planned.

Phillippe shared that Witherspoon initially slapped him while he was improvising mean things to say to her character.

The moment was then added into the final scene.

14 Ryan Got Sick Filming The Breakup Scene

Fight Scene Creul Intentions

As Reese Witherspoon and Ryan Phillippe were dating for some time before filming began, the stars could play up their natural chemistry and accurately portray two people falling in love. Although their closeness helped with building the relationship, it also came with its drawbacks too. As they onscreen couple’s relationship began to deteriorate, audiences watched as the two got into a very heated argument.

Along with the impromptu slap that we mentioned earlier, another unplanned reaction occurred when the argument got too emotional.

Kumble shared: “I think Ryan talks about it often — he threw up on set. And it was one of those things where I just let the cameras roll.”

13 Katie Holmes almost played Annette

Katie Holmes in Dawson's Creek

In the search for the sweet and innocent Annette, producers looked for a young but popular actress that could capture the role perfectly. Casting turned their attention on Katie Holmes, having just started her time as Joey on Dawson’s Creek.

The popularity of Dawson's Creek made her a hot commodity and possibly the best candidate for the film.

However, Kumble expressed his doubts about Holmes portraying the role feeling that they “needed someone with a little more strength of character." While the studio wanted Holmes, Kumble considered actress Vinessa Shaw (Hocus Pocus) for the lead role. Both sides came to a stalemate since neither would budge on their choice and neither actress got the role. However, Phillippe led them to the perfect actress for Annette.

12 Reese Witherspoon almost said no to the part

Annette Cruel Intentions

While stuck arguing with the studio for the best actress to play Annette, Kumble arrived on the idea of using Phillippe’s girlfriend Reese Witherspoon. Having already starred in popular films such as Pleasantville and Fear, her rising stardom would be the perfect fit for the movie. However, Witherspoon required some convincing to take on the role.

In an interview with ABC News, Kumble revealed how the power of alcohol helped to sway the young actress. He stated, “So, basically, we took Reese out to dinner... and we ended up getting [inebriated]… And I literally got down on my knees and begged her: 'Please, it'll be 15 days, you'll be great.'” Their plan worked and Witherspoon agreed to the role.

11 The "Happy Accident" During The Kissing Scene

Cruel Intentions Park Scene

Cruel Intentions did not hold back on the intimate scenes between the characters. In on particular scene, Kathryn then helped Cecile learn about kissing in a very hands-on way. The kiss itself became one of the most talked about moments in the movie and even won the MTV Award for Best Kiss.

The scene was shot a couple of times, but the first take remained in the movie.

Why? Because of a “happy accident” that occurred when the two actresses parted after the kiss (yes, we mean the spittle moment). At first, someone pointed out the “accident” and asked for a retake. However, the moment was deemed “beautiful” so it remained in the film.

10 Reese Witherspoon Thought Annette was a "doormat"

Cruel Intentions Annette and Sebastian Car Scene_

The character of Annette became the primary focus of Sebastian in the film Cruel Intentions. Sebastian initially only saw her as a conquest and set his goal to possess her.

When Witherspoon agreed to discuss the movie, she had some hesitance given the type of role she would be playing. Although Annette’s character seemed like the typical “good girl” persona, she envisioned more potential for the role. In fact, she expressed her concerns to Kumble, stating she wanted the character to have a bit more spice to her personality.

In the end, Kumble and Witherspoon fleshed out that character more to ensure she wasn’t simply “a doormat.”

9 Selma Blair's Very Method Audition

Selma Blair Cruel Intentions

With the cast of Cruel Intentions nearly complete, casting had some particular rules for the role of Cecile. Considering the character’s young age and very adult actions later in the film, cast directors had to be careful about who they chose.

Any potential actresses had to be 18 and older. As such, they began each audition by asking the age of the actress in question. This simple question helped actress Selma Blair secure the role.

She took the opportunity to respond in the way the bratty Cecile would.

Kumble shared with Cosmopolitan: “It was the smartest audition I've ever seen in my career… 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.”

8 The hidden meaning of Annette's wardrobe

Cruel Intentions truly pitted good against evil throughout the film. As the villains of the movie, Sebastian and Kathryn preyed on the kinder and more naïve students at their school. Although they had no idea of their manipulative ways, their innocent victims trusted them and many of them succumbed to their dark behaviors.

To further illustrate the two sides in this story, the costume designers incorporated contrasting outfits in light and dark colors. For example, the dynamic between the morals of Sebastian and Annette clearly displayed in the colors they wore. Designers dressed Witherspoon in lighter colors to reflect her sweeter nature. Phillippe, on the other hand, often wore darker, expensive outfits to reflect his personality.

The subtle color differences added another layer to the film’s overall symbolism.

7 The Final Scene's Song Cost A Fortune

Cruel Intentions Ending

One of the most recognized songs incorporated into the movie was The Verve’s "Bittersweet Symphony". The song became an integral part of the final scenes of the movie as the audience watched Annette getting her revenge on Kathryn.

The song perfectly accompanied Annette as she drove away in Sebastian’s car with his journal next to her.

Kumble shared how the song almost didn’t make it into the movie in an interview with ABC News. He said, “That was another example of me writing a scene perfectly to music without getting the rights. That was a nightmare… So we're like, 'Oh, let's get the rights from The Verve.’ But then you find out The Verve doesn't own the rights, The Rolling Stones own the rights.”

Unable to find another piece that worked perfectly for the scene, the studio ended up paying the hefty fees for the rights to the song.

6 The oldest star played the youngest actress

Selma Blair Sarah Michelle Gellar Cruel Intentions

Early in casting, the director and the casting team made sure they did not cast any underage actresses for the role of Cecile. Given the very adult situations she would be placed in, it would have been inappropriate and uncomfortable to expect an underaged actress to do. Interestingly enough, the selected actress, Selma Blair, ended up being one of the oldest cast members in the main cast.

At the time of filming, she was 27 years old and yet, expected to play the role of a 15-year-old girl.

Sean Patrick Thomas, who played her love interest, was almost 30 during the production of the movie. As for the other main cast? Phillippe was 25, Witherspoon was 23 and the youngest of the group, Gellar, was only 22 years old.

5 Sarah Michelle Gellar starred in a failed reboot pilot

The majority of the spinoffs from Cruel Intentions seemed to lack one key factor: the missing original cast. With the failure of the original TV show in 1999, NBC decided to try its hand on bringing the movie to the small screen.

In 2015, the network announced a new TV series that would pick up where the original film left off.

The new lead character would be the child of Sebastian and Annette. In addition, Gellar would reprise her role as Kathryn for the series. The series looked to be heading to air soon and even included promotional shots from around the set. However, the series ran into issues as cast members began to leave the planned series. By 2016, the series was canceled and never aired.

4 Gellar Returned for the Cruel Intentions Musical

Since the Cruel Intentions TV pilots couldn’t seem to get things right, the rights to the film and its characters moved to the bright lights of Broadway. AM New York reported a "three-performance ‘pop-up’ premiere" and "an extended Off-Broadway run. Its score is made up of songs from the film’s soundtrack and other ’90s pop hits.”

Gellar even returned for the musical production but in a very unique way. Playing Kathryn once again, she provided the pre-recorded warning that played before the play began.

In as icy of a voice as possible, she warned the audience to turn off their cell phones and not to take pictures. If you didn’t listen, she would “cyber-shame you into oblivion.”

The musical extended its run due to popularity, coming to an end in April of this year.

3 Little Red Riding Hoodie

Selma Blair in Cruel Intentions

Although her brattiness remained throughout the movie, Cecile still started off as a rather innocent girl. The step-siblings gradually found a way to manipulate her thanks to her secret feeling for her music teacher, Ronald Clifford. As Sebastian continued to trick Cecile into being with him, the costume designers slipped in a subtle clue to symbolize Cecile’s loss of innocence.

Costume director Denise Wingate explained: “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.”

The truth about the costume choice makes the scene a lot more interesting, doesn’t it?

2 The Smashing Pumpkins Refused Music Rights

The Smashing Pumpkins

One of Kumble's writing techniques was writing to music, using the lyrics and melodies to guide his thoughts. Although this helped to tap into his creativity, this technique also had his faults.

Certain scenes were connected to specific pieces of music that he used to inspire him. Later on, he tried to get the rights to those songs since they fit perfectly. Unfortunately, not every artist wanted to be a part of his project. For the scene when Annette and Sebastian physically express their love for one another, Kumble listened to The Smashing Pumpkins’ “To Sheila”.

Sadly, lead singer Billy Corgan rejected his request for the rights to the song. In the end, the chosen song was “Colorblind” by Counting Crows.

1 Inspired by Welcome to the Dollhouse

Welcome to the Dollhouse

The plot of Cruel Intentions revolved around the deceptive and manipulative actions of Sebastian and his step-sister, Kathryn. Their own devious plans affected the lives of many students from their school. However, the overall concept of the story originated from Les Liaisons dangereuses, a 1782 French novel written by Pierre Choderlos de Laclos.

Kumble’s film adaptation wasn’t the first to be made, but set itself apart from others by taking a modern take on the tale. His inspiration for the setting change came about after watching Todd Solondz's Welcome to the Dollhouse. This dark comedy shed a very dim light on the horrors of high school. After viewing the film, he decided to take the high school aspect of the film and apply it to Les Liaisons dangereuses.


Do you have any other trivia to share about Cruel Intentions? Leave it in the comments!

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