Welcome back to Manchester Prep. In 1999, audiences gaped (and gasped) as Hollywood’s teen royalty engaged in sexual debauchery and 1-percenter power games in Roger Kumble’s erotic, darkly comedic modern classic, which returns to theaters Friday in honor of its 20th anniversary.

Here, in an EW exclusive, the filmmakers and cast members revisit the original tale of gossip girls and pretty little liars. The Beginnings After watching 1996’s coming-of-age black comedy Welcome to the Dollhouse, playwright Roger Kumble felt inspired to pen a dark story centered on a young cast. So he took the soulless aristocrats of the 18th-century French novel Les Liaisons Dangereuses and reimagined them as depraved upper-class Manhattan teens.

ROGER KUMBLE (writer-director): It’s just a great story. It’s got drama and comedy and tragedy, and you can’t do that so often these days. Movies have to fit in a box. You don’t know where to put Cruel Intentions in the aisle, you know?

Completed in 1998, his script landed in the hands of friend Heather Lieberman, who’d just begun working with producer Neal H. Moritz at Sony (who would go on to rev up the Fast and the Furious franchise). Moritz immediately jumped on board, even though Kumble had never helmed a film. (To put it in Cruel Intentions verbiage, he was a directing virgin.)

NEAL H. MORITZ (producer): This script stood out [with] its attitude, its brashness, its setting. Roger’s voice was so fresh, I would have done anything to make the movie.

HEATHER LIEBERMAN (co-producer): In our staff meetings, we always talked a lot about the kinds of films we wanted to do, and we were really looking for [stories about] young people in adult situations. This certainly fit the bill.

KUMBLE: I had the arrogance of youth on my side. [Laughs] Nowadays I’d be terrified! I was not one of those kids who played with Super 8 cameras. I knew I had to hit it out of the park on my first go or they’d never let me do it again.

Image zoom Courtesy of Roger Kumble and Sony

The Casting A script like Cruel Intentions (or Cruel Inventions, as it was originally titled) was hard to ignore. The story featured a pair of scheming, semi-incestuous stepsiblings — alluring, coke-cross-wearing Kathryn and womanizing, Jaguar-driving Sebastian — who make a bet over whether Sebastian can deflower Annette, the daughter of the new headmaster at their prep school. An ensemble of up-and-coming young actors quickly lined up to dive into the risky (and risqué) material.

SARAH MICHELLE GELLAR (Kathryn Merteuil): My reps thought it was a terrible idea for me. They were like, “You’re Buffy! People have this great idea of you — why shatter it?” I was like, “That’s the point.” I was so determined to be a part of this, I would pester Neal to find out what party Roger was going to, and then I would show up. I would find out when they were having meetings in Neal’s office, and then I would show up.

RYAN PHILLIPPE (Sebastian Valmont): There was something about this script that just felt like something that could last. The first time I finished reading it, I was like, “There’s no way they can make this.” [Laughs]

JOSHUA JACKSON (Blaine Tuttle): Teenage roles were written very two-dimensionally: You were the jock or the nerd or the hot one. I was a precocious 19- or 20-year-old who expected roles to be intelligent and stupid and bad and funny and over-the-top. [This] elevated the material.

MARY VERNIEU (co-casting director): One person we had thought of for Selma’s part was Brittany Murphy. She was coming off of Clueless, but she ultimately ended up not being available, so then we went in looking for someone, and we found Selma, who was a discovery for us. She really brought something so special to Cecile… I feel like I can actually still picture her coming in and her audition outfit.

SELMA BLAIR (Cecile Caldwell): I was the oldest in the cast but newest to the industry. I had auditioned for, like, 60 things [around then] and didn’t get them because I was over 18. I went in [for this], and Roger and I began this obnoxious banter. He said, “How old are you?” and I was like, “How old are you?” I wasn’t trying to cage around my age. I was just sick of all these auditions. [Laughs] He probably thought I was a nutball.

ANNE McCARTHY (co-casting director): Roger knew exactly who he wanted. When you’re in our position, that’s really comforting. And he’s just a lot of fun. Everyone on the movie, the actors, the crew, the producers — they became a family.

VERNIEU: All these movies [like I Know What You Did Last Summer, Can’t Hardly Wait, The Faculty, and more], it was all the same group of kids coming up. I’m sure we discussed Jennifer Love Hewitt [for a role].

McCARTHY: If I tried to make a list of teenage actors now, it’d be 30 pages long. There are so many shows — the kids on Netflix, the kids on The CW — it’s just a bigger universe.

MORITZ: We were all starting our careers at the same time, and we were all among the same social circles, and it just was one of those things where literally it all just came together perfectly. Everybody that we wanted to do the movie ultimately did the movie.

JACKSON: I was so young, I couldn’t rent a car in L.A. [Costar] Reese [Witherspoon] hooked me up with the one car company that would rent to underage people, which I’ve always remembered and been grateful for. In the beginning I had to take cabs and she’d be like, “Oh, no, no, no, that’s not going to work.”

Image zoom Courtesy of Roger Kumble and Sony

Speaking of Witherspoon, rounding out the cast with the actress, Phillippe’s then girlfriend, took a little scheming — with good intentions, of course.

REESE WITHERSPOON (Annette Hargrove): I thought we were all just going to dinner as friends, and then Roger and Ryan asked me to do the movie. [Laughs] I remember a lot of coercing.

KUMBLE: It had nothing to do with “Oh, let’s cast [Ryan’s] girlfriend.” The world hadn’t seen Election, but we knew how talented Reese was. He just happened to be going out with her at the time.

PHILLIPPE: We drank a lot of wine. [Laughs] We were wooing her! She loved the movie for me, but it wasn’t a great part at the time for her. She helped Roger turn it into one.

KUMBLE: It’s true, she came and sat with me for a week, and we worked on the dialogue together. Annette was the character most removed from me. There’s no way the movie would have its success if it weren’t for [Reese’s] talent as a writer.

WITHERSPOON: I remember finding Annette too demure and too much of a woman influenced by a guy’s manipulations. I was starting what I guess became my bigger mission in life — of questioning why women were written certain ways on film. The Sex Kathryn and Sebastian’s wager produces a web of scandals and steamy scenes that gave the film its titillating reputation. Sebastian disrobes poolside to seduce Annette. Kathryn teaches naive rival Cecile how to French-kiss. Even supporting players wind up between the sheets.

GELLAR: As an actor, all you want to do is get lost in a role, and to be that delicious and to really have no moral compass, I mean… You can’t do that in life!

PHILLIPPE: When [Kathryn] says, “You can put it anywhere”? Like, whoaaaaaa.

GELLAR: I don’t know that if it had been cast differently, that it would have been as comfortable. I’d known Ryan for years. There was a comfort there that allowed us to push boundaries.

SEAN PATRICK THOMAS (Ronald Clifford): Roger was always throwing curveballs to heighten the kinkiness. My scene [with Sarah], in the script it says, “Ronald hides under the bed.” When I showed up on set, Roger was like, “Hey, I want you to put on these tiny little briefs and this feather.” I was like, “Oh man, oh-kay!”

GELLAR: Let me tell you, there would be no rating in the world that would be appropriate for a Roger Kumble director’s cut. [Laughs] They need to donate his brain to science.

JACKSON: 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. [Laughs] But I was more concerned with making my character real. You didn’t see a lot of gay characters, period. But [especially] gay characters that weren’t caricatures, so I wanted to make sure that, even with dialogue that was beautifully over-the-top, he still felt like a real person.

Image zoom Courtesy of Roger Kumble and Sony

PHILLIPPE: I felt okay with [showing] my butt. Everybody has a butt, it’s really not that graphic. [Laughs] So many guys on Twitter are like, “That’s the moment I knew I was gay,” and there have been guys like, “I behaved like Sebastian to get laid!” [Laughs] Which I never did.

BLAIR: I’d never kissed a girl before. I remember I was like, “What if I really am a horrible kisser?” My mother, after seeing it for the first time, told me, “Honestly, Selma, did you have to use so much tongue? That poor Sarah, she looks so delicate, and then you just have that Goliath in her mouth.” [Laughs]

GELLAR: All I remember thinking was “I could kiss Selma all day!” Her skin was so soft. My skin is really sensitive, so when I kiss on camera a lot, it gets raw.

KUMBLE: I got to revisit the movie a few years ago, when we put up the musical. I was like, “Whoa, I don’t know if we should do this!” With some of these scenes, I was like, “Oh my God.” It was another time, you know? Not that that’s an excuse.

One of those scenes saw Sebastian luring Cecile over to his house — and blackmailing her into sex.

PHILLIPPE: At that age, it didn’t feel as lascivious. I’m not sure I saw it the same way you would see it in retrospect.

GELLAR: What they’re doing to her is horrible. We could never make that scene today, let’s put it that way.

BLAIR: But Cecile enjoyed almost every moment of it! She was so odd. [Laughs] She wasn’t a shrinking violet. She wasn’t upset. She was almost delusional, for the better.

KUMBLE: I’d come from comedy, and sometimes I wrote comedy just to ease into those horrible moments. I don’t know if that’s a good or a bad thing… It’s nothing that I’m, like, proud of, but in that situation, because she falls out of frame and I have a comic button to the scene, you didn’t have to go, “I’m turning this off.” The Couple’s Spat In the film, Sebastian eventually falls in love with Annette, and a jealous Kathryn forces him to end the relationship. As they filmed the breakup scene, things got so heated that Witherspoon went off script and slapped Phillippe, who vomited afterward.

PHILLIPPE: I was so actor-y back then and romanticizing going through torture to do good work. And I was in love. [Laughs] [The offscreen relationship] certainly made things more real, or more intense. You have a deeper connection.

WITHERSPOON: I hit him, and it upset him. We were young, and we just had heightened emotions. But it was great. It was a special time.

Image zoom Courtesy of Roger Kumble and Sony

The Retribution A brokenhearted Sebastian dies in an accident. In an emotional scene, Kathryn gets her comeuppance at his funeral when Annette and Cecile distribute Sebastian’s tell-all journal, which exposes her as a drug-addled, amoral sinner who toyed with her classmates’ love lives and caused her stepbrother’s death.

GELLAR: 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?

BLAIR: I was scared to give her that book in real life. I thought I would trip on my way to Kathryn, even though I trust Sarah.

KUMBLE: When I originally wrote it, it was smaller. It was set in a room with Annette and Kathryn, and it just didn’t have that oomph. Heather pushed me to give it a bigger ending.

LIEBERMAN: She had to be publicly shamed. The crux of the movie is from a teenager’s point of view, right? At that age, your reputation is the most important thing. Things feel so big, so that public persona she worked so hard to cultivate needed to be shattered.

Image zoom Everett Collection

The Denouement The movie ends with Annette driving away from the city as the Verve’s “Bitter Sweet Symphony” plays. The producers almost couldn’t afford the track, as it samples a cover of the Rolling Stones’ “The Last Time.”

KUMBLE: I wrote the ending to that song because it just aligned perfectly. And then we found out it’s the Rolling Stones. [Laughs]

MORITZ: The song cost close to a million dollars, which was probably 10 percent of the budget. When we thought it was going to be hopeless to get, we tried 200 other songs in its place. We could not find anything even close to it. It was well worth it.

The film didn’t dominate the box office when it was first released. In fact, its R rating meant younger moviegoers often snuck in.

KUMBLE: I was hearing that it was supposed to do better than it did. There were theaters that had these posters — I wish I got them — that said, “We will not sell tickets to anyone under 17 for Cruel Intentions,” so people were sneaking in. We didn’t win the weekend… I wish I could go back in time, and be like, “Don’t worry about it!” [Laughs]

PHILLIPPE: A lot of the responses I got in my 20s and 30s was, “I saw this movie when I wasn’t supposed to.” It was an epidemic that weekend of kids sneaking into theaters to see Cruel Intentions.

KUMBLE: The movie, it took time, you know? I’ve never had the benefit of a big win opening weekend. But [it’s] standing the test of time, so it’s great.

Still, Cruel Intentions became a seminal entry in teen pop culture and catapulted many of its leads to greater stardom.

WITHERSPOON: It was just a really interesting time in the cultural zeitgeist where these teen films were doing very well, and we were at the center of them all. We were all trying to navigate how to have serious acting careers and still take advantage of that. I was so young, I didn’t know what I wanted to do with my life. [Laughs] Ryan and I had Ava in 1999, so I was probably talking about mom things. I was doing the best I could to raise a little girl.

GELLAR: It was all a letdown [afterward]. [Laughs] This was such a perfect experience on every level. The material was so elevated, the cast was so ridiculously talented… It was all in a bubble.

PHILLIPPE: I became somewhat reactionary to the stigma of being in teen movies, and I looked to be more serious and was wary of being categorized as a “teen actor.” [Laughs] When I watch it now, I wonder, “Why didn’t I do more comedic stuff?” I’m like, “I’m pretty fun in that!” [Laughs]

Image zoom Everett Collection

In the decades since, the film has spawned multiple attempts at prequels and sequels, as well as a jukebox musical of ’90s hits.

WITHERSPOON: We all had a moment when that play came out. We thought it was hysterical — Ryan and I were definitely laughing about that, and then Sarah and Selma and I went and saw it. It was fantastic.

KUMBLE: 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.

LIEBERMAN: Except at the very end, you never see them in their uniforms. A “teen movie” is about the world of high school, but you were never between the walls of a classroom. Gossip Girl did that too — they were hardly ever at school.

WITHERSPOON: It’s a piece of classic literature about how people manipulate each other. I’m sure there could be some new iteration of it with new people. It’s just about somebody who’s imaginative, like Roger, coming up with an idea.

PHILLIPPE: In the era of social media, the GIFs people use from the movie keep it alive. You really appreciate that stuff as you get older and you have so many disappointing experiences in the industry.

GELLAR: As an actor, all you want to do is make art that stands the test of time, so to be a part of a movie that 20 years later is still relevant and still important? That’s the holy grail.

BLAIR: It was so naughty and so funny, but also such a classic, even if it’s not politically correct. It’s a story that endures, and people do still act that way. They just don’t want people to know about it.