Set in a posh prep school in New York City, Cruel Intentions is a tale of two very disturbed stepsiblings who have way more money than they know what to do with. Half of the movie they’re warming up to each other, and the other half they’re messing around with the students at their school.
One of their victims is the timid and innocent Annette, played by Reese Witherspoon. She gets preyed on by the male lead, Sebastian, but ends up making him fall for her instead (aha! everyone’s favorite plot twist).
Here’s a behind the scenes look at one, nay, THE most twisted film of 1999.
It Was Supposed to Be Called Cruel Inventions
The movie shows various cunning schemes involving different degrees of deception, trickery and manipulation−all of which originate from one little bet between two twisted stepsiblings, one of whom appears heartless (Sarah Michelle Gellar… yes).
The film’s title perfectly captures its theme. Indeed, the movie’s leads have cruel and selfish intentions. Interestingly, according to Sarah Michelle Gellar, the film’s original title was supposed to be Cruel Inventions.
Sarah Michelle Gellar Wanted to Shed Her Buffy Image
Sarah Michelle Gellar became a household name after she took on the lead role in Buffy the Vampire Slayer. For seven seasons, viewers at home were enthralled with her character. The show became a cult classic. Benefitting from all the fame, Gellar kept expanding her acting career.
She perfected her role as Buffy to the point where it became hard for her to separate herself from that persona. After being cast to Cruel Intentions, the actress decided to dye her hair and shed her Buffy image once and for all.
The Slap Annette Gave Sebastian Wasn’t Planned
Sebastian and Annette’s relationship had a rocky start, but the two young lovers gradually grew to trust one another. Annette grew closer to Sebastian, and Sebastian found himself falling in love with her, which was never part of the plan.
Sebastian fell so much in love with Annette that he lost interest in his stepsister, Kathryn, who was his prize for getting Annette to fall for him in the first place. Kathryn forced Sebastian to break up with Annette, which led to a heated argument in which Annette slapped him across the face. In reality, the slap wasn’t planned. It just happened while Phillipe was improvising mean things to say to her in the scene.
Ryan Got Sick During the Breakup Scene
Reese Witherspoon and Ryan Phillippe were dating for a while before filming began, so the stars already had natural chemistry coming into it. But their love life had its drawbacks. As the filming progressed, their relationship started to deteriorate.
Apart from the improvised slap mentioned earlier on this list, another unplanned reaction happened when the breakup argument got way too emotional. Ryan Phillippe actually threw up on set. Roger Kumble, the director, enjoyed the couple’s real, raw reactions.
Katie Holmes Was Almost Annette
In the search for someone to play sweet and innocent Annette, the film’s producers looked for someone young and popular who could capture the character perfectly. They turned to Katie Holmes, who had just started her career as Joey on Dawson’s Creek.
Kumble, however, expressed his doubts about hiring Holmes, saying that they “needed someone with a little more strength of character.” Kumble thought of hiring actress Vinessa Shaw of Hocus Pocus instead. Ultimately, the casting team and Kumble decided on Witherspoon.
Reese Witherspoon Almost Said No
Unable to reach an agreement with the casting directors over who would play Annette, Kumble got the idea of casting Phillippe’s girlfriend at the time, Reese Witherspoon. She had already starred in popular movies such as Pleasantville and Fear, and he believed that she would make a perfect fit for the film.
Witherspoon, on the other hand, needed some convincing. In an interview with ABC, Kumble talked about how the power of alcohol helped convince the young actress. “So, basically, we took Reese out to dinner… and we ended up getting [wasted]. And I literally got down on my knees and begged her: ‘Please, it’ll be 15 days, you’ll be great.’”
The Award-Winning Kissing Scene
If there’s one thing that can be said about Cruel Intentions, it’s that they certainly didn’t hold back on the intimate scenes between the characters. In one particular scene, Kathryn helps Cecile learn how to kiss.
She does so in a very hands-on manner. The kiss between the girls became one of the most talked about scenes in the film. It even won MTV’s Award for Best Kiss! The scene was shot numerous times, but the first one (the one with a bit of spit) made the final cut.
Reese Witherspoon Thought Her Character Was a “Doormat”
In the film, Witherspoon’s character, Annette, became Sebastian’s primary focus. He initially saw her as nothing more than a conquest. When offered the role, Witherspoon hesitated because she felt like Annette was just a typical, boring “good girl.”
She turned to Kumble with her concerns, stating that she wanted Annette to have a bit more fire in her. They worked together to flesh out a character that was more than, in Witherspoon’s words, “just a doormat.”
Selma Blair Nailed the Audition
All potential actresses for the film had to be 18 and older. The audition process went as follows: the casting directors began each audition by asking how old the actresses were. This question helped actress Selma Blair land the role.
Blair responded in the same way that bratty Cecile would. “It was the smartest audition I’ve ever seen in my career,” Kumble shared. “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.”
The Hidden Meaning Behind the Wardrobe Choices
As the film’s villains, Sebastian and Kathryn preyed on the naive students at their school. Their innocent victims had no clue they were being manipulated, and many of them trusted the wicked stepsiblings and their conniving ways.
To further illustrate the good and bad characters in the film, the costume designers chose contrasting outfits in light and dark colors. For instance, Sebastian and Annette’s morals were clearly displayed in the color of their clothes. Witherspoon wore lighter colors to reflect her kind and bright nature, and Phillippe, on the other hand, wore darker outfits.
Bittersweet Symphony Cost Them a Fortune
One of the most memorable songs in the movie’s soundtrack was The Verve’s “Bittersweet Symphony.” The single became an integral part of the film’s final scenes as the viewers watched with delight how Annette got her revenge on Kathryn.
The tune perfectly accompanied Annette as she drove off in Sebastian’s car with his journal by her side. Kumble told ABC that the song almost didn’t make it into the film: “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.” They ended up paying a hefty sum.
The Oldest Character Was Played by the Youngest Actress
Early on, the director and the casting crew made sure not to cast anyone underage for the role of Cecile. Given the sexual situations she would be placed in, it would have been pretty uncomfortable to put a minor in those racy scenes in front of the camera.
Selma Blair ended up getting the role. And she was actually one of the oldest ones in the main cast! At the time of filming, she was 27 years old (her character was supposed to be 15). Sean Patrick Thomas, who played her love interest, was 30 years old.
How Old Was Reese Witherspoon in Cruel Intentions?
As for the other actors from the main cast, Phillipe was 25 years old, Reese Witherspoon was 23, and the youngest of the bunch, Sarah Michelle Gellar, was only 22 years old.
Witherspoon said she felt like a terrified little girl at the time of filming. The reason? She was pregnant. She was married to her co-star Ryan Phillipe and the two welcomed their child in 1999.
“To be completely candid, I was terrified, too. I got pregnant when I was 22 years old, and I didn’t know how to balance work and motherhood. You just do it, you know I didn’t know if I was going to have steady work, too,” Witherspoon opened up.
Little Red Riding Hoodie
Although Cecile’s bratty personality persisted throughout the movie, she still remained a rather innocent girl. The stepsiblings gradually found out how to manipulate her thanks to her vulnerability and the secret crush she had for her music teacher, Ronald Clifford.
In the film, Sebastian tricks Cecile into being with him. And the film’s costume designers jumped on the opportunity to slip in a subtle cue in the scene, one that would symbolize her loss of innocence. They made Cecile wear a red hood, just like little red riding hood, who went off to see the big bad wolf.
Kumble Wrote the Script While Listening to Different Songs
One of Kumble’s ways of writing was putting music in the background, using the song’s lyrics and melodies to influence and guide his thoughts. While this helped him tap into his creativity, this technique also had its downsides.
There were scenes he felt were connected to specific pieces of music, and, later on, when he tried to get the rights to those songs, he ran into some trouble with a lot of them. Sometimes he had to pay a fortune, and sometimes, no amount of money could buy him the rights.
The Smashing Pumpkins Refused Music Rights
One example of a song that should have been on the soundtrack but wasn’t is “To Sheila” by The Smashing Pumpkins. When writing the scene where Annette and Sebastian get intimate, Kumble listened to the song on repeat.
Unfortunately, The Smashing Pumpkins’ lead singer, Billy Corgan, rejected Kumble’s request to use their song. Ultimately, Kumble had no other choice but to look for a different song. He ended up playing Counting Crows’ “Colorblind” instead.
So Close to Being Sebastian
Before casting Phillippe as Sebastian, Kumble had his mind set on another up-and-coming young star. “I was also looking at Jonathan Rhys Meyers at the time, because a lot of young Hollywood back then wanted to do it,” the director told The Telegraph.
Kumble said that “Ryan just had that kind of Valmont air about him.” Eventually, the Irish star would go on to play in films like Bend It Like Beckham, Match Point and Mission: Impossible III.
Getting Bunny on Track
Witherspoon wasn’t the only cast member who needed convincing to sign on to Cruel Intentions. Christine Baranski said that she originally thought of passing on the role of Cecile’s strict mother, Bunny Caldwell.
As with Witherspoon, Kumble resorted to begging. “I had to be talked into doing that one,” Baranski told the LA Times, “It was going to be shot during my first year’s hiatus from Cybill and I was anxious to go home and be with my kids. The director begged and begged me and said, ‘It’s only a few scenes.’”
An Alternate Ending
Cruel Intention’s ending is probably the movie’s best scene. It’s dramatic, surprising, satisfying, and with Bittersweet Symphony in the background, it’s just a pleasure to watch. But it could have ended differently!
In an alternate version of movie’s dramatic ending, Sebastian is still hit by a car, but not because he jumped to protect Annette from getting hit. Instead, he stops hitting Ronald when he sees Annette approaching them and gets unexpectedly run over by a vehicle when crossing the street to greet her.
Minors Snuck Into Cinemas
So, what made Cruel Intentions such a hit that hundreds of minors risked getting caught and decided to sneak their way into the cinemas? Apart from the generous number of sexual scenarios, there was something else that drew people in.
It was the perversion and the odd relationship between the stepsiblings. Not only are we fascinated with sex, but we’re also fascinated with anything out of the norm. Put that together and you get a guaranteed blockbuster hit.
What Is Cruel Intentions About?
Cruel Intentions has it all. It shows the dark side of human nature, but also the light. Sebastian starts out as a heartless, cocky, “I’m sick of sleeping with these insipid Manhattan debutantes” kind of guy. But towards the end of the film, he’s a changed man.
According to Kumble, Cruel Intentions did well because it was way more than a story about mean teens: “It’s one thing to have juicy dialogue and mean teens, but it’s also a tale of redemption. This guy’s soul is saved. That’s what I think resonates,” he explained.
“Everybody Does It”
Selma Blair and Michelle Gellar have come up with another reason why the movie has endured the test of time. According to Blair, the movie was naughty and funny and far from politically correct. But most importantly, it was relatable.
People do still act that way,” she told Entertainment Weekly. Gellar agreed, adding, “Everybody does it! It’s just that nobody talks about it.” While not all of us want to sleep with our stepsiblings, many of us struggle with envy and forbidden desires.
The Day Gellar Kept Silent
In between takes, the main cast laughed, ate, talked, fooled around together, and rehearsed lines. The experience overall was fun and creative. But in the final days of filming, Sarah Michelle Gellar took a step back to focus on getting into character.
While preparing for the movie’s final scene (the funeral), Gellar kept quiet on set. “That was the one day where I was more focused than having fun, where I probably wasn’t hanging out with anyone. Because if that scene didn’t work, then what’s the point?”
Diving Into the Deep End
Cruel Intentions is full of steamy shots between men and women, men and men, women and women, brothers and sisters, and if they had more time, they would probably add some orgies to the mix. So, with so much sexual tension, how was the vibe between the actors on set?
According to Joshua Jackson (Blaine): “The vibe on set was playful. And that was nice because my first day was doing this scene where I’m giving a bl– job. That was diving into the deep end,” he told Entertainment Weekly.
Blair Was Concerned About Kissing a Girl
Gellar and Blair’s kiss was truly unforgettable. A little before shooting it, Blair was feeling jittery. “I’d never kissed a girl before. I remember I was like, “What if I really am a horrible kisser?” she confessed in an interview.
According to Gellar, she was far from a bad kisser. “All I remember thinking was ‘I could kiss Selma all day!’” she told Entertainment Weekly, “Her skin was so soft. My skin is really sensitive, so when I kiss on camera a lot, it gets raw.”
David Schwimmer Helped Make the Movie
Director of Cruel Intentions, Roger Kumble got his start in the early ‘90s working as a playwright and director. Still hoping to make a name for himself in Hollywood, Kumble finally gained some attention thanks to a little project he did that involved one of Friends’ huge stars.
In a sit down with Cosmopolitan, the director revealed: “I put a play up in 1997 and I got David Schwimmer to be in it, at the height of Friends. And that was a game-changer for me.” His newfound status gave Kumble the drive and recognition to push Cruel Intentions to the silver screen.
Fun fact: Cruel Intention’s script took Kumble 12 days to write!
Inspired by Welcome to the Dollhouse
Cruel Intentions’ plot revolves around the deceptive and manipulative behavior of Kathryn and her stepbrother Sebastian. Their devious plans affect the lives of many other students that go to their school. The idea for this plot was inspired by a French novel from 1782 called Les Liaisons Dangereuses, written by Pierre Choderlos de Laclos.
Kumble’s film adaptation was a modern take on Laclos’ tale. After watching Todd Solondz’s Welcome to the Dollhouse, Kumble combined the two and took the high school aspect of Todd’s film and applied it to Pierre’s French novel.
The “I Know What You Did Last Summer” Reunion
After he finished writing the film’s script, Kumble started looking for the cast. He lacked a studio to back the movie but began the process of producing it, nonetheless. Although he initially thought of actor Jonathan Rhys Meyers as the lead male, another director convinced him to cast Ryan Phillippe and Sarah Michelle Gellar instead.
How come? Because of the successful horror flick, I Know What You Did Last Summer. According to Kumble, he was approached by another director who told him: “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.”
The Movie’s Prequel and Sequel
With an edgy storyline, a diverse cast, and a brilliant soundtrack, Cruel Intentions became one of the most talked-about films of 1999. Thanks to its favorable reputation, several spin-offs have been made as a continuation of the plot.
The first one, Cruel Intentions 2, starring Amy Adams and Kathyrn Merteuil, served as the franchise’s prequel. Cruel Intentions 3 wasn’t very connected to the previous films other than the fact that the lead character was Kathyrn’s cousin.
The Most Dramatic Supporting Role Ever
Another minor role filled by an actor who would go on to dominate headlines was the star of The Bachelor, Charlie O’Connell, who played Kathryn’s boyfriend, Court Reynolds, who dumps her to be with Cecile.
Interesting little fact: Before Gellar dated Freddie Prinze Jr., she and Jerry O’Connell, Charlie’s older brother, were a thing. They started dating after meeting on the set of Scream 2, a while before she began filming Cruel Intentions.
Familiar Faces
Another actor who landed a small but memorable role in the movie was Dawson Creek’s star, Josh Jackson, who played Blaine Tuttle, Sebastian’s gay partner in crime. Another one was Ugly Betty’s Eric Mabius, who starred as the football player that Sebastian ends up blackmailing.
Tara Reid is also in the film, acting as a good girl who got tricked by Sebastian. Later that year, she hit it big after landing a role on American Pie. All these actors had small roles in Cruel Intentions but went on to do other great things.
Gellar and Blair Remained BFFs
Since shooting the movie back in the late ‘90s, Gellar and Blair, in particular, have become good friends and remained quite close over the past two decades. Gellar even posted a picture of her and Blair on her Instagram, captioning it with “girl crush, now and forever.”
Blair commented back, writing that Gellar was her “forever girl.” Looks like all those years haven’t been able to wash away the sweet memory of kissing each other out there in the park. We haven’t forgotten that kiss either.
Sarah Michelle Gellar Took Part in a Failed Reboot Pilot
Most spinoffs that came after the film lacked one key element: the original cast viewers loved and longed to see again. NBC tried bringing the movie to the small screen by calling in some of its actors.
In 2015, NBC announced that they would be launching a new TV show that would pick up where Cruel Intentions left off. The lead character would be Sebastian and Annette’s child. And Gellar would even be brought back to play Kathryn. Ultimately, the show an into some trouble, and cast members gradually left the planned series.
Gellar Joined the Cruel Intentions Musical
Since getting Cruel Intentions on TV didn’t work so well, the plot and its characters moved to Broadway to see if they could show it there instead. AM New York announced a three-performance pop-up premiere.
Sarah Michelle Gellar ended up joining the musical production. She played Kathryn and provided the play with a pre-recorded warning that came out of the speakers a little before the play began. In her cool, icy voice, she told the audience to turn off their cell phones. If you didn’t listen, she would “cyber shame you into oblivion.”
A Look Back
Phillippe and Witherspoon were one of Hollywood’s hottest young couples when they filmed Cruel Intentions. They remained together for several more years, despite the ups and downs involved in being in the same industry and under similar pressure.
In 2007, after eight years of marriage, they went their separate ways. In 2015, Phillippe spoke to Larry King saying: “When we got together, we were so young I think it can create issues with two people in this industry because there’s so much noise that goes along with it.”
Where Are They Now? Sarah Michelle Gellar (Kathryn)
It’s been a little over two decades since the film first premiered. Here’s what the cast has been up to.
Sarah Michelle Gellar, who played Kathryn, continued her work as the star of Buffy the Vampire Slayer, a part that earned her several Teen Choice Awards and a Golden Globe nomination.
Gellar has also appeared in movies such as Scooby-Doo (2002) and The Grudge (2004). She’s also starred in TV shows such The Ringer and The Crazy Ones. Gellar is perfect for horror films. Really, there’s just something eerie about her (in a good way!).
Ryan Phillippe (Sebastian)
The movie’s good-looking, charming, heart-breaking lead was played by Ryan Phillippe. After Cruel Intentions, he went on to score roles in films such as Company Man (2000), Setup (2011), Antitrust (2001), Crash (2004), and The Lincoln Lawyer (2011).
Ryan has also appeared as Bob Lee Swagger on Shooter from 2016 to 2018. He hasn’t been very active in the industry lately, but his last projects include the film Alive II and The Sound of Philadelphia.
Reese Witherspoon (Annette)
After playing the innocent yet clever Annette, Witherspoon landed the lead in the 2001 blockbuster hit Legally Blonde, in which she co-starred once again with Selma Blair. She later worked on other films, including Vanity Fair (2004), Wild (2014), and A Wrinkle in Time (2018).
Reese’s performance in A Wrinkle in Time was one of her best ones yet and it won her an Academy Award for Best Actress and a BAFTA Award for Best Actress. Apart from acting, she’s also produced several movies, including Wild and Gone Girl.
Selma Blair (Cecile)
After her roles as the naïve and bratty Cecile, Blair went on to co-star alongside Reese Witherspoon in Legally Blonde. She’s also starred in movies such as Storytelling (2001), The Sweetest Thing (2002), and “Hellboy” (2004).
Selma has gone on to do TV as well. Some of her small-screen credits include Kath & Kim on ABC and Fox’s Anger Management. As for her personal life, Blair has a son who she shares with her ex-partner Jason Bleick. In 2018, she announced that he had been diagnosed with multiple sclerosis.
Sean Patrick Thomas (Ronald)
Sean Patrick Thomas played Ronald, Cecile’s music teacher and the man she has the hots for. After his stint on Cruel Intentions, Thomas went on to star alongside Julie Stiles in the 2001 film, Save the Last Dance.
Thomas’ also starred in Barbershop (2002), The Curse of La Llorona (2019), and the Fountain (2006). As for the small screen, Thomas has acted on shows such as CBS’ The District and The CW’s Ringer and Vixen. He has two kids with his wife Aonika Laurent.
Joshua Jackson (Blaine)
Jackson had already scored a few roles before taking on the part of Sebastian’s friend in Cruel Intentions. He played Charlie Conway in the Mighty Ducks and landed the role of Pacey Witter in Dawson’s Creek (1998).
Jackson starred as Pacey Witter until 2003. He’s also appeared in films such as Aurora Borealis (2005) and Bobby (2006). As for the small screen, Jackson has starred in shows like Fringe and The Affair. He’s married to actress Jodie Turner Smith.
Eric Mabius (Greg McConell)
Before playing the macho athlete in Cruel Intentions, Mabius scored roles in films including Welcome to the Dollhouse (1995), I Shot Andy Warhol (1996), and The Minus Man (1999). He went on to star in other films such as Resident Evil (2002) and Venice Underground (2005).
In the early ‘00s, Mabius starred in several TV shows: Scandal, Ugly Betty, The L Word and Chicago Fire. One of his recent projects (2019) includes a role as a mayor named Liam Clark in the TV film It’s Beginning to Look a Lot Like Christmas.
Christine Baranski (Bunny Caldwell)
Baranski was a successful actress before playing the role of Cecile’s snooty mother in Cruel Intentions. After the film, she landed roles in films such as How the Grinch Stole Christmas (2000), Chicago (2002) and Mamma Mia! (2008).
As for the small screen, Baranski has scored roles on shows like CBS’ The Big Bang Theory and The Good Fight. She’s one respected actress and has come a long way since her Broadway debut back in 1980 in the play Hide and Seek!
Swoosie Kurtz (Dr. Regina Greenbaum)
Swoosie Kurtz was an award-winning actress long before she played Sebastian’s shrink, Dr. Greenbaum in Cruel Intentions. Over the years, she’s won Tony Awards for her part in plays like Fifth of July and The House of Blue Leaves.
Kurt has also received Emmy nominations for her great performances on NBC’s Love, Sidney and Sisters. After Cruel Intentions, she secured guest roles on TV shows like Desperate Housewives and Lost. Her recurring roles include parts in shows like ABC’s Pushing Daisies and CBS’ Man With a Plan.
Tara Reid (Marci)
Before making a brief appearance in Cruel Intentions, Tara Reid played a recurring role as Ashley on NBC’s Days of Our Lives. Her breakout role was in 1998 in the movie The Big Lebowski. Since then, she’s starred in movies such as American Pie (1999) and The Pussycats (2001).
Reid has also appeared in movies such as Alone in the Dark (2005) and Sharknado (2013). She’s also landed a guest role in Scrubs. Reid has been through her ups and downs, but lately she’s been trying to revive her career and shed her party-girl reputation.