12 Things You Never Knew About 'Cruel Intentions'

Screenwriter and director Roger Kumble shares some trivia about his 1999 movie.

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1. Welcome to the Dollhouse sparked the idea for the screenplay.

"I'd just seen Todd Solondz's Welcome to the Dollhouse, and I was like, Wow … fucked up high school. Never seen this. It was so dark. And it was one of those moments when you're just walking across the street, and the idea popped into my head to do Dangerous Liaisons set in high school. And I mulled it over for a year.

"Then 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. It was a pretty dark play. It was about a screenwriter who's just looking to seduce this innocent d-girl [short for development girl, a person in film production who scouts potential movie ideas]. I put that up and it was a hit out in LA. So I had some heat, and I didn't want to lose it. Literally, the day the play went down I went to Mexico and I wrote Cruel Intentions in 12 days."

2. I Know What You Did Last Summer helped the movie get made.

"I met Neal Moritz who's now like, Neal Moritz [producer of Fast & Furious21 Jump StreetI 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.' And it was Ryan Phillippe and Sarah Michelle Gellar. 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. Columbia picked it up as a negative pickup [meaning the studio would finance it but Moritz would own the movie]."

3. Katie Holmes was up for Reese Witherspoon's part as Annette; Reese wound up getting the part after Ryan and Roger took her out and begged her.

"We got into disagreements over who was going to play Annette. The studio wanted Katie Holmes, who was just starting to do Dawson's Creek. And I liked this actor Vinessa Shaw. And they were both great. But this was early Katie, and I thought we needed someone with a little more strength of character. And we just couldn't agree. And then, literally, I was hanging out with Ryan one night and I was like, 'What about your girlfriend?'

"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.' I'm like, 'Anything, anything, anything.' She wanted to strengthen the character, and she was right. And she and I got together, and we gave Annette more bite so she wasn't a doormat. And I'm very grateful to her for that."

4. Selma Blair went Method for her audition.

"It was the smartest audition I've ever seen in my career. I remember having to ask all the actors coming in how old they were because that scene [when Ryan's character, Sebastian, gets Selma's character, Cecile, drunk, and then goes down on her] is, for lack of a better word, rape. So we were like, 'All right, we're gonna shoot this. It's going to be dicey if we get away with it. But we can't have an underage girl.' So we were bringing in all these people and they were all good, but 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. She came into the audition as the character and didn't show me that there was Selma; I said, 'This is the person.'"

5. Ryan wasn't particularly worried about shooting such dark material.

"We were all young and didn't know. I remember Ryan coming up to me when we were shooting, and he goes, 'When you break down this movie, it's really about me wanting to have anal sex with my sister.' [When Sebastian and Sarah Michelle's character, Kathryn, make their bet, she says, 'You can put it anywhere.'] I said, 'Well, that's an interesting way of looking at it. I never thought of that.' He's like, 'The whole plot turns on that.' And I go, 'Yeah, it does.' I didn't realize it at the time.

"I think probably because my background was more in comedy, I was able to button the [darker] scenes with a bit of a joke and make them more palatable. In [the rape scene] I have him go out of frame and then Selma makes some silly kind of interjection and then falls out of frame. I kind of was excused.

"But I remember going to the theaters at the time it came out, and it was an R-rated movie and they were cracking down hard on kids getting into R-rated movies. And there were signs in the theaters saying, 'No one under 17, especially for Cruel Intentions.' I should have taken a photo of it. All the sex that went on in that movie—they did not want the kids to see it."

6. Speaking of sex scenes: Yes, shooting the Ryan/Reese sex scene was awkward. Of course it was.

"There were two scenes where I kind of gave them their space and made the set as comfortable as possible: The lovemaking scene—in any situation like that, you shut the set down—and the breakup scene. For the lovemaking scene, there were a couple of movies I referenced ... Theo van de Sande, who shot Cruel Intentions, who was really my film teacher because I had only directed theater, we watched a lot of film together … So I go, 'This is what I'm going for. I don't want it to be exploitative, I want it to be beautiful.' There was a lovemaking scene in The Player, with Tim Robbins and Greta Scacchi, for example. So once Ryan and Reese were comfortable and Theo and I were comfortable and they saw what I was trying to do, there was that scene.

"What I do in situations like that in anything I'm working on is I just drop the pretentions of the job and go, 'OK, let's deal with the elephant in the room. I'm about to film a sex scene with you and I feel weird.' And then usually they're like, 'No, no, no, we get it—it's weird.' And then I go, 'How do I make it less weird; let's all be on the same page.'

"If you notice in the movie, there's no nudity except Ryan. Because I don't need to see Annette nude; I don't need to see Kathryn nude. The words are speaking for it. So even though we kind of sweated them up in the sex scene, he's on top. We didn't have to go there."

7. Ryan vomited while shooting the breakup scene.

"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. 'Let's go back, do it again, let's go back.' I want to be professional, but until I feel like we have it, you just have to go. As a director, you're like, 'I'm not going to be the most liked person today.' I don't think we did too many takes. But, you know, you get what you need to get. You really want to see him ripping his heart out."

8. Back to the sex scene: It was originally set to a Smashing Pumpkins song, but Billy Corgan refused to sell the rights to his music. The Counting Crows swooped in at the very last minute with "Colorblind."

"I wrote a lot of the movie to music. It's like that first-time filmmaker thing: 'This would be perfect for this.' For that scene, there was this Smashing Pumpkins song called 'To Sheila,' which fit perfectly. If you turn off the Counting Crows and play the scene to 'To Sheila,' it actually works quite nicely. And [it seemed like] we were getting the song, it was great; Billy Corgan was watching the movie. It was down to the wire, and then they give me the call: 'Smashing Pumpkins said no.' And we were like, 'Oh, fuck.' Because we were all in agreement then—the producers, the studio, and I: This is the right song.

"Then everyone had their favorites and we couldn't agree. So we were trying every song in that scene, which we all knew was pivotal. And I remember I was championing a Neil Finn song. But they weren't as jazzed about it as I was and we were at a standstill. Then the music supervisor came in and said, 'Adam Duritz saw the movie and loved it and he wrote this song and they're recording it tonight or tomorrow night, but here's a demo of it.' And we heard the opening, the piano, and we were like, 'Oh my god, this is great. We love this.' And Neal and I, we went to Adam's house, or the Crows' house they were renting at the time, that night or the next night, and watched them record 'Colorblind.' We put it on the film and it was great."

9. The movie almost got made without "Bittersweet Symphony" as well.

"That was another example of me writing a scene perfectly to music without getting the rights. That was a nightmare. It just fit amazingly [in the final scene]—the strings hitting as she's breaking down on the podium and then you cut outside right when the song kind of kicks in and it just accomplished everything. 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 [because it samples an orchestral version of the Rolling Stones song 'The Last Time']. So it was a headache. It was one of those things where the studio was like, 'Try another song.' And we kept trying and trying and no one could agree. And the studio was like, 'Let's just pay for it.' We paid for everything, but we really paid for that one."

10. There was a porn star on set; she flashed everyone.

"There was a scene where Ryan is on the phone with Annette. It's on the DVD of the deleted scenes. Originally you kind of pan around him, and in the background are two naked cheerleaders, oiling themselves up. Just to show what a cad he was at that stage. And for that, I wanted to see some gratuitous nudity. But I didn't want some girl crying in her trailer [about having to get naked]. My parents didn't raise me that way. I didn't want to force anybody. So I was like, "I know! I'll hire an adult film star; they have no problem with that."

"So we found this girl, her name was Alisha Klass, and she was the biggest star in adult films in the late '90s, and she had the most innocent looking, cute face—all natural, the '90s. So we met her and I'm like, 'Hey! We'll give you a line, it's more of a humorous scene.' And she was really sweet; she was great. And then two days later, I'm working in my office, working on rewrites, and my costume designer comes in, she goes, 'We have a problem. The women on set have a problem.' I was like, 'What?' She goes, 'Your actor's at catering and she's wearing just a fishnet whatever, body skirt, and is basically flashing all of us.' So it was like a no-good-deed situation. Where I just didn't want to force an actor to go topless in a scene and I got the one person with no inhibitions. And now I'm like the pig in front of all the women on the crew.

"The scene got cut because during the testing process we're like, 'Eh, too much; not worth it.' I was just throwing in a joke. But she was very sweet. She brought some DVDs for some of the grips."

11. The Sarah/Selma spit string was a happy accident.

"I forget who, but someone said, 'We need to go again, there's saliva connecting them.' And Theo 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. They did win the MTV Award for best kiss."

12. The movie might next become a play.

"I'll tell you this: I'm adapting it for the stage. Not a musical. It's a work in progress. Rather than reboot it or any of that, I was like, 'This really could live on the stage.' If you look at the staging of Cruel Intentions, it's like a play. It's mostly two people in a scene, three people in the scene. I've been working on it for about a year now; we might try to workshop it. What's going to happen, I have no idea."

Patti Greco

Patti Greco is a freelance writer and editor based in Brooklyn. She was formerly the entertainment director of Cosmopolitan.com and a staff editor at New York Magazine and Vulture.