Cruel Intentions is more than just a film; it’s a cultural touchstone…
On March 5, 1999 Cruel Intentions premiered and it’s pretty safe to say that the story about a group of wealthy teenagers attending high school in New York City quickly gathered a loyal fanbase. Written and directed by Roger Kumble, the teen flick was the first of it’s kind, a modern retelling of the classic 1782 French novel Les Liaisons dangereuses by Pierre Choderlos de Laclos, with a cast of young actors that included Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair in pivotal roles.
“Cruel was exciting because, for me, I look for things that’ll make an impact and something that’s different. And teen movies at that point were teen movies,” Gellar told Entertainment Tonight back in 2019. “We were coming out of a John Hughes-era and moving into these sort of frothy, romantic comedies, and to take material like Les Liaisons Dangereuses, and give it to teens and that material, it was sort of the first of its kind.”
Cruel Intentions was a surprise box office success when it was released in the spring of 1999 and over the years the film has more than maintained its grasp on our attention becoming a cult favourite, a rare feat for any movie. Twenty-five years later the teen drama remains a quintessential late-90s film, blending a little seduction, a little revenge, a little manipulation and some serious drama. In celebration of the film’s 25 year anniversary here are 15 lesser-known facts about Cruel Intentions that might surprise even its most ardent fans. Of course, these little tidbits only scratch the surface of what makes this movie so enduringly and one of the greatest teen flicks ever.
1. Inspired by a classic
As we mentioned above, Cruel Intentions is a modern adaptation of Pierre Choderlos de Laclos’ 1782 novel Les Liaisons dangereuses, but it’s not the only famous film inspired by the French novel. Cruel Intentions shares this literary ancestry with the award-winning 1988 film Dangerous Liaisons, directed by Stephen Frears from a screenplay by Christopher Hampton, based on his 1985 play Les liaisons dangereuses, itself adapted from the 1782 French novel. Dangerous Liaisons (which won three of its seven Oscar nominations) starred Glenn Close, John Malkovich, Michelle Pfeiffer, Uma Thurman, Swoosie Kurtz, Mildred Natwick, Peter Capaldi and Keanu Reeves. 1989’s Valmont, directed by Miloš Forman and starring Colin Firth, Annette Bening, and Meg Tilly, was also an adaptation of Les Liaisons dangereuses.
2. Welcome To The Dollhouse was also an inspiration
Apparently 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.
3. Real-life romance
The chemistry between Ryan Phillippe and Reese Witherspoon in Cruel Intentions was not just cinematic. The duo met in 1997 before filming began at a party for Witherspoon’s 21st birthday. Their on-screen romance translated into a real-life relationship, leading to their marriage on June 5, 1999 and the birth of two children (daughter Ava Phillippe and son Deacon Phillippe). Unfortunately they didn’t’ live happily ever after…The couple’s marriage officially ended on October 5, 2007, with final divorce arrangements settled on June 13, 2008, according to court documents.
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4. A different title
Initially, the film was set to be called Cruel Inventions but was later changed to Cruel Intentions. The film’s original title was revealed by Sarah Michelle Gellar in 2016 on Instagram in a Throwback Thursday post.
“#throwbackthursday ok one last one because I was feeling nostalgic – and yes #CruelInventions was the original title,” she wrote. “This pic was 1998 at our kick off dinner.”
5. The I Know What You Did Last Summer connection
Part of the reason Ryan Phillippe and Sarah Michelle Gellar ended up snagging their roles as Sebastian Valmont (based on the Vicomte de Valmont) and Kathryn Merteuil (based on the Marquise de Merteuil) in Cruel Intentions was because of their work in the hit 1997 teen horror I Know What You Did Last Summer thanks to the two film’s sharing the same producer, Neal Moritz.
“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.’ And it was Ryan Phillippe and Sarah Michelle Gellar,” writer and director Roger Kumble revealed to Cosmo in 2014. “And they were great. And I was just excited to get my movie made, so I was like, ‘Great!’ Once we cast Sarah and Ryan, then it got heat; we had two hot actors.”
6. Casting could have been different
Cruel Intentions almost looked very different with many prominent actors and actresses considered for the main roles. Katie Holmes almost starred as Annette Hargrove and Christina Ricci auditioned for the role of Cecile Caldwell.
“This was early Katie, and I thought we needed someone with a little more strength of character,” writer and director Roger Kumble said of ultimately passing on the Dawson’s Creek star.
On the other hand, the role of Sebastian Valmont saw interest from actors like Ewan McGregor and Jake Gyllenhaal and almost went to Jonathan Rhys Meyers.
“I was also looking at Jonathan Rhys Meyers at the time, because a lot of young Hollywood back then wanted to do it,” Kumble told The Telegraph in 2019. “Ryan just had that kind of Valmont air about him.”
7. The production designer used mostly dark colours on purpose
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.”
8. However, Witherspoon was purposely dressed in light colours
“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.
9. The cost of the journal
Kathryn’s cocaine-laced cross necklace is one of the film’s most iconic props but another significant prop is Sebastian’s journal, which plays a crucial role in the narrative. The journal shows all of Sebastian’s inner thoughts: his conquests, his description of the bet, and a page on Kathryn, which finally exposes her manipulative and deceitful ways, including the fact that she hides a vial of cocaine in a crucifix necklace she wears around her wrist. The journal was recently auctioned off for an astonishing $4,000, signifying its importance to the film’s legacy.
10. That kiss
Back in 1999, Sarah Michelle Gellar and Selma Blair’s onscreen kiss was a pretty big deal. It even won Best Kiss at the 2000 MTV Movie Awards, with the pair recreating the kiss on stage. Scandalous!
Not included in the original script? That iconic string of spit. “I forget who, but someone said, ‘We need to go again, there’s saliva connecting them.’ And [cinematographer] Theo [van de Sande] was like, ‘No, it’s beautiful.’ And I was like, ‘No, it’s hot. I mean, we’ll go again, but I think it’s cool,'” Kumble told Cosmo. “So it was a happy accident. And it’s kind of been remembered for that.”
When it came to actually filming it, Gellar once said, “Selma was afraid she would suck at kissing me. But she didn’t!”
Blair (who was actually 27 playing the 15-year-old freshman Cecile) admitted to some initial nerves, but revealed Gellar had some too, saying, “Besides kissing my sister years ago in a game of truth or dare, I had never kissed a girl up to the point where I had to kiss Sarah. We shot our kissing scene on the last day of filming. And, it actually felt great. On our way from L.A. to NYC to film the scene in Central Park, I said to Sarah, ‘Tomorrow we get to make out!’ She was like, ‘Shhhh. Don’t speak.'”
Shot with hundreds of extras and photographers around, the kiss ended up making news the following week. “[We] saw headlines that said something like, ‘Sarah spends a day in Central Park with a friend,'” Blair remembered. “I guess they all had their telescopic lenses ready that day.”
11. 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.
12. A star-studded soundtrack
The film’s 1999 soundtrack became almost as iconic as the movie itself, featuring tracks from artists like Placebo (“Every You Every Me”), Blur (“Coffee & TV”, Fatboy Slim (“Praise You”), Marcy Playground (“Comin’ Up From Behind”), Counting Crows (“Colorblind”), and The Verve (“Bitter Sweet Symphony”). The film’s soundtrack peaked at #60 on the Billboard 200 and played a significant role in setting the film’s tone and mood.
13. Alternate ending and deleted scenes
Spoiler alert: Sebastian still dies! Just in a slightly different way. In an alternate version of the film’s dramatic ending, Sebastian is still hit by a car, but not because he is protecting Annette from being hit. Instead, he just stops fighting Ronald (Sean Patrick Thomas) when he sees her approaching and gets unexpectedly hit by a vehicle when going to cross the street to talk to her.
But, wait there’s more… Several scenes were cut from the final version of the movie, including an alternative ending where Annette drives off with Sebastian’s journal. These deleted scenes are available on the DVD release, offering fans a glimpse into what might have been.
14. There was a stage adaptation
The film’s story and characters proved so compelling that Cruel Intentions was adapted into a musical. This stage version premiered in Los Angeles in 2015, blending the narrative with hits from the 90s, showcasing the story’s adaptability across different mediums.
15. Cruel Intentions has a prequel and a sequel
While Cruel Intentions was a huge hit in 1999, it resulted in two more movies which were frankly — not nearly as good. Both follow-ups were direct-to-video movies — the prequel titled Cruel Intentions 2 in 2001 and the sequel titled Cruel Intentions 3 in 2004.
