In 1999 the teen drama Cruel Intentions premiered and it's safe to say that the story about wealthy teenagers attending high school in New York City quickly gathered a loyal fanbase. Cruel Intentions is an adaptation of Pierre Choderlos de Laclos' novel Les Liaisons dangereuses written in 1782 — however, this teen movie was not set in 18th-century France. The movie starred Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair, and pretty much immediately after its release, it was evident that it would become a '90s teen classic.
Today, we're taking a look at some facts most probably don't know about Cruel Intentions. From who almost got cast to which scenes were improvised — keep on scrolling to find out!
10 Katie Holmes Was Almost Cast To Play Annette And Jonathan Rhys Meyers Was Almost Cast As Sebastian
Kicking the list off is the fact that Hollywood star Katie Holmes almost starred in Cruel Intentions as Annette Hargrove. However, screenwriter and director Roger Kumble revealed that he thought the movie "needed someone with a little more strength of character."
On the other hand, the role of Sebastian Valmont almost went to Jonathan Rhys Meyers but eventually, the filmmakers opted for Reese Witherspoon and Ryan Phillippe (who were also dating at the time).
9 Reese Witherspoon Originally Said No To The Role
While Roger Kumble didn't want Katie Holmes, he certainly struggled quite a bit with getting Reese Witherspoon to say yes to the part. In an interview for Cosmopolitan, the filmmaker revealed that he and Ryan Phillippe teamed up to convince the at-the-time 22-year-old actress:
"So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk. 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.'"
8 This Was Ryan Phillippe And Sarah Michelle Gellar's Second Movie Together
As fans know, in the movie Ryan Phillippe and Sarah Michelle Gellar play stepsiblings Sebastian Valmont and Kathryn Merteuil. However, the 1999 teen drama isn't the first movie the two starred in together.
In 1997 the two actors played the lead characters in the slasher movie I Know What You Did Last Summer alongside Jennifer Love Hewitt and Freddie Prinze Jr.
7 At The Time, 27-Year-Old Selma Blair Played 15-Year-Old Cecile Caldwell
When the auditions for Cruel Intentions started, the filmmakers were very clear that they wanted all of the cast to be 18 or older, but a fun fact is that the older actress amongst the stars who played the teens in the movies was the at-the-time 27-year-old Selma Blair. Frankly, the actress totally pulled of teenager Cecile Caldwell perfectly — she certainly had us fooled!
6 The Scene In Which Annette Slaps Sebastian Was No Scripted
While the movie mostly followed the script, director Roger Kumble still allowed space for improvisation and change. When it comes to the break-up scene between Sebastian and Annette, Ryan Phillippe revealed that the slap was improvised:
"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. Roger loved it so much he incorporated it into the scene. So basically I got slapped around for a couple of hours."
5 And The Saliva In The Infamous Kissing Scene Was An Accident
Let's move onto the infamous kiss between Sarah Michelle Gellar and Selma Blair which won in the Best Kiss category at the 2000 MTV Movie Awards. Here's what director Roger Kumble revealed about it:
"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'. So it was a happy accident. And it's kind of been remembered for that."
4 Sarah Michelle Gellar Dyed Her Hair Brown For The Role
Actress Sarah Michelle Gellar was a big star in the late 90s, mostly due to the fact that she was starring in the ultra-successful drama show Buffy the Vampire Slayer.
However, while Buffy Summers was a blonde, Sarah decided that Kathryn Merteuil should be a brunette and she dyed her hair for that role — mostly to shed her Buffy image.
3 The Clothing Played An Important Role
Costume designer Denise Wingate certainly did a great job with everyone's outfits and here is what she revealed about her choices for Annette's clothing:
"Her palette was softer and sweeter but confident. 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."
As far as Cecile's outfits go, those weren't an accident either. Here's what the costume designer said about Cecile's looks:
"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."
2 '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.
1 And Finally, The Movie Also Resulted In A Cancelled Television Show
In 2015 it was announced that Cruel Intentions will be getting a remake show starring none other than Sarah Michelle Gellar. The show was written by Roger Kumble however in the fall of 2016 — to everyone's disappointment — NBC announced that they decided not to go through with the show due to scheduling issues.