An Oral History of Clueless – Vanity Fair

When Clueless eventually landed in the hands of producer Scott Rudin and Paramount Pictures, Frazier was off the project, and Marcia Ross was brought on as the new casting director. With Ross, a new set of producers—including Rudin, Adam Schroeder, Robert Lawrence, and Barry Berg—and Heckerling, Caplan, and Paramount executives all now at the decision-making table, the second attempt to cast Clueless began in the fall of 1994.

Amy Heckerling: [Casting Josh] was the hardest. I had a vision in my head and it wasn’t jelling with people out there. When I’m writing, I usually have little pictures of what I imagine the guy looking like. And I had the Beastie Boy: Adam Horovitz. There was something smart and funny about him.

Marcia Ross, Clueless casting director: Because I was always reading actors, I knew a lot of young actors, and I was able to come up with a bunch of thoughts for parts and sort of come in with ideas and show her.

Paul Rudd was one of those people.

Paul Rudd, Josh: When I auditioned for it, I had also asked to read for other parts [including Christian and Murray].

I thought Murray was kind of a white guy wanting to be black. I didn’t realize he was actually black. Also I thought: I haven’t seen that character before, the white guy who’s trying to co-opt black culture. But, well: that character is actually going to be African-American. Oh, O.K.

I think I read for Elton as well. But Amy said, “What do you think of Josh? Do you want to read for that?” So I did.

Amy Heckerling: I remember I saw Paul, and I really liked him. There were still more people to be seen [though].

Adam Schroeder: He needed to be older, and [Alicia] was young, but we didn’t ever want it to feel not natural when they ended up together. There was the whole stepbrother thing, even though they weren’t related at all, so we really wanted to be careful and cast that perfect person. We read a lot of actors.

Twink Caplan: Amy and I loved [Paul] right off. He hadn’t done that much, but he was cute and he was sweet. He reminded me of George Peppard. Not in his acting, but the nose. He was very engaging.

Adam Schroeder: We tested him, and we knew he was very, very top-of-the-list.

Paul Rudd: I knew that they must have been kind of interested, because they had me back a few times. Honestly, what I remember when I was auditioning and meeting Amy for the first time is making some joke about Shakespeare preparing something from a monologue. I’m sure it was not a very good joke or anything. But I remember she really laughed at it. Almost more than anything else, I remember, in talking with Amy in the auditions, I was like: Oh, she’s cool. I click with her.

Marcia Ross: We had him on hold for a long time, but they weren’t really ready to decide. Then … finally, they decided—they cut him loose actually. And it was hard. They really liked him, but they just couldn’t commit to it, and he was offered another movie. He took this Halloween movie. I remember he cut his hair for that.

Paul Rudd: That Halloween movie was my first movie, which I wasn’t so sure I wanted to do. I had a manager at the time who was like, “You should do this.” And then I remember I got Clueless, and he’s like, “You shouldn’t do this.” That’s how good that manager was.

I remember really vividly where I was, just kind of walking down the street, and I was like, “Man. I don’t know. Why don’t I just cut off all my hair?” And I just walked into a barber shop and they just buzzed my head. Then, I want to say a week later or something, I was in a restaurant and Amy Heckerling was there.

Amy Heckerling: I went, “What the fuck did you do?” He said, “I didn’t think I had the part.” I said, “Oh my God, hardly any time went by—I didn’t finish seeing everybody. Yeah, I want you. You cut your hair?”

Paul Rudd: I was weirdly cavalier about it. In a way, it wasn’t really on my radar. And I remember I said, “Well, you know: if it’s supposed to work out, it’ll work out.”

Marcia Ross: We kept seeing more people and [were] not sure we had it….

I’m fairly sure Zach Braff read for Josh. I had hired a casting director in Chicago to put people on tape for the role while I was still searching for an actor to play the role. He was going to [Northwestern] at the time. My note was that he was good.

We screen-tested several guys with [Alicia] on film, and she and Paul—he really was good with her. From the minute he came in to the minute he got the part—and it was such a long journey, really, that one in particular—there was always this sort of harking back to: remember Paul? I can’t explain it to you. He never went out of consciousness.

Paul Rudd: I don’t remember the actual call saying I got the part…. I wasn’t sure about [Halloween]. But Clueless: no, I wanted to do that one.

Donald Faison, Murray: I met Paul [during auditions]. I met Breckin Meyer; I’d seen him in [Freddy’s Dead: The Final Nightmare] or some shit like that. I thought that was really freakin’ cool.

Adam Schroeder: You know, it was also funny when Breckin Meyer and Seth Green came in, and it was down to the two of them for Travis. And it turned out they were best friends…. But I’m sure each wanted the part.

Then one of the top contenders for Tai was an actress named Alanna Ubach. Alanna was Seth Green’s girlfriend [at the time]. So there was a version of Seth Green and his girlfriend playing Tai and Travis at one point. But obviously they cast Breckin and Brittany, and we were so happy….

Brittany [Murphy] came in, and she was such a standout. She naturally had a funny spirit. Which was great, because Alicia had a different kind of comic spirit. She had a much more sardonic thing. And the chemistry between the two of them was really lovely.

Friedman observes Silverstone as she shoots the scene in which Cher prepares for the “brutally hot” Christian to come over and watch “Sporadicus.”

Amy Heckerling: When I met Brittany, I was like: I love her. I want to take care of her.

She was just so bouncy and giggly and just so young. I mean, when you saw her, you just smiled.

Twink Caplan: Right away Amy knew she surely had the part.

Adam Schroeder: It was the second time she was coming in, and we were doing the mixing and matching. We had her stay in the casting with us and Alicia…. She never had been involved in that end of it. I remember there was just a joy. Everything was very exciting to her, and it was fun to be around her. I think she knew it was a really big deal for her. I think all the actors did.

Alicia Silverstone: I remember her audition. When she came in, it was just like: Oh my God. Stop the press. This is the girl.

Stacey Dash, Dionne: I actually didn’t get the whole script at first. I just got the sides [an excerpt from the script]. I went in, and I mean, just from the sides, I knew it was mine. So I went in. I nailed it. They called me back in, again, to read with Alicia. We had great chemistry. So that was in the bag.

As soon as I met [Alicia], she was as sweet as can be. Of course, I was nervous because it’s an audition process. But she just made me feel so at ease, and so did Amy … she made everything just about having fun.

Amy Heckerling: In my brain, Dionne was like royalty. I wanted someone that felt like they were part of a royal family in some country somewhere. So they weren’t acting snotty—they were just in a different realm. [Stacey] had that. She didn’t have to act like “I’m a snotty bitch”—she just had that feeling of power and grace, as though she was ready to wave to the public.

Stacey Dash: I went back and read with Terrence Howard and Donald Faison, [who were auditioning] to play Murray. And of course Donald got the role. And then that was it.

Amy Heckerling: I do remember that I saw Mel Brooks’s movie [Robin Hood: Men in Tights]. And I loved Dave Chappelle. I met with him in New York.

Donald Faison: I didn’t [know that Chappelle was considered for Murray]. That would have been awesome, too.

Amy Heckerling: Donald had a much more kid-like energy. And Dave [had] a very cynical, grown-up, funny, comic kind of thing that I felt was maybe a little too edgy.

Adam Schroeder: Donnie Faison came in and became one of our favorites for Murray. Terrence Howard also was one of the top contenders.

Donald Faison: We grew up together pretty much. I’ve known Terrence since … I was nine—you know what I mean?

Right before I went to Los Angeles, I don’t know what happened. They wanted me is what I was told. He was like, “Yeah, go get it, man. Go do your thing.” But he never told me [earlier] that he was up for the role. I didn’t find out he was up for the role until after my final audition in New York, when I was about to go to L.A.

I remember when they called me and told me I got the part, and me telling all my friends that I was going to be kissing Stacey Dash, and them chasing me around the complex that I lived in.

Stacey Dash: I was crossing the street [in L.A.]. I’ll never forget it. I got the phone call that I got the job, and I almost got hit by a car. I was just jumping up and down in the middle of the street, screaming because I was so excited.

Marcia Ross: What often would happen in the sessions is [Amy] might like somebody, but then she wanted to see them again for another role. So somebody I remember, like Jeremy Sisto, might have read easily for three roles.

Jeremy Sisto, Elton: I could have read for a couple of different characters, and then I decided to read for Elton because I thought he was funny. It just seemed like more fun to do the more extreme character—like the worst of the bunch, as opposed to the romantic guy.

Marcia Ross: He read for Josh and Elton that same day, and [Amy] said, “No, he’s an Elton.”

Amy Heckerling: Well, that voice is very distinctive. It felt very entitled. I felt like that would go better with Elton than with a more insecure, angry-at-the-world kind of person [like Josh].

Adam Schroeder: I really loved Sarah Michelle Gellar, who was on All My Children at the time. She played Erica Kane’s daughter, and she was just kind of wicked, beautiful. I showed Amy tapes of her. We ended up offering her the part of Amber. There became a big negotiation for All My Children to let her out. It was just for a couple of weeks, and they absolutely stuck their feet in [and] wouldn’t let her.

Elisa Donovan, Amber: I had no idea about Sarah being a front-runner for the role of Amber. I do remember reading all of the smaller female roles for Marcia.

Adam Schroeder: [Elisa] was really funny, really beautiful. I remember she reminded us of Ann-Margret. It’s an old-school reference, but she had that kind of sexy, ginger beauty. She got the wit and cynicism of Amber. You want her to be one of those characters you love to hate. But you don’t really hate her.

Marcia Ross: The Justin Walker part is a great story because we were really having a tough time casting. You had to find a person who kind of was gorgeous that she could have the crush on, but you didn’t want: “Oh yeah, he’s gay.” He had to be different than the other guys.

Amy Heckerling: That guy had to be cute [and] had to be in a different time period from everybody else. He had to have his own style. He had to be reminiscent of another kind of 50s, 60s kind of thing.

Adam Schroeder: Jamie Walters. He came in [to read] for Christian.

Amy Heckerling: I remember thinking he had an interesting look.

Justin Walker, Christian: This thing for me was like pulled out of nowhere. My career was really kind of floundering. I was in between agents; I was working with somebody on a freelance basis; I was between apartments; I was sleeping on someone’s couch. I got a phone call to come in and read for this film, and I was given the choice to read for Josh or for Christian, and when I looked at the material, the way the rhythm, the vocabulary, and everything else about the part [of] Christian—it was a no-doubter.

Marcia Ross: He read for me in the morning for Josh, when I was in New York. I had Amy in the afternoon for callbacks, so it was a short period of time. I gave him the sides. I said, “When you come back this afternoon, I don’t want you to read Josh. I want you to read Christian. Can you prepare it?” And he came and he did it and that was it.

Twink Caplan: It was this unique part that somebody had to be so many things and had to have a little bit of a foot in another era. And these were young kids. I don’t think they really related that much to Frank Sinatra. … We couldn’t find it and then we finally found the guy to do it. And he was very sexy.

Justin Walker: I will never forget—I was managing a bar called the Overtime Bar and Grill [in N.Y.C.], right next to Madison Square Garden, basically. I was speaking to my agent on a pay phone—a pay phone, mind you! And she told me that I got it, and I dropped the phone and started sprinting south on Eighth Avenue.

Amy Heckerling: I wanted somebody [for Mel, Cher’s dad and Josh’s ex-stepdad] that would feel like the normal parts for [him] to play would be a hit man. And I loved Jerry Orbach in Prince of the City. And I also loved Harvey Keitel. I wanted it to be somebody that could be really scary, and anybody else would be [frightened] of him, except Cher. It would never occur to her that he was being anything but funny.

Marcia Ross: Jerry Orbach—we made an offer to him. I remember [Amy] really loved and wanted [him] to play Mel, and he couldn’t get off his [TV] show.

Amy Heckerling: Jerry Orbach—the dates wouldn’t work. Harvey Keitel we couldn’t afford. And then … my friend told me about Dan Hedaya.

Dan Hedaya, Mel: I didn’t audition for it. Scott Rudin was the producer, and I just was offered this job. I know I liked it. I especially liked the relationship [between Mel and Cher]. I’m an uncle to quite a number of nephews and nieces, and I don’t have my own children. But I’ve been close to children my whole life. I liked how it was written and how the character was written. The tough love.

Amy Heckerling: I wrote [Mr. Hall] for [Wally Shawn]. I know that we auditioned people because we had to. I was not allowed to just say, “This person’s doing this and that’s it.”

Wallace Shawn, Mr. Hall: That is Hollywood. The director is far from being the sole decision-maker. Even if she’s also the writer, she’s not the financial backer, so … I think you have to cooperate with a lot of other people. If all the Paramount executives had said, “We don’t like him and we want you to use so-and-so,” she would have had to do that. I don’t think I was brought into the process. She was certainly not keeping me posted—she probably did all that and then said, “Come play the part.”

Nicole Bilderback, Summer: When you’re reading the script, when you see dialogue on paper, you think, Oh, O.K. This is fun. But back then, before the movie was released, when you read lines like “What-ever,” you’re like, O.K., what is this?

I actually read for two parts: I read for Summer and for Heather, and they liked me for both, but they ended up casting me as Summer.

The girl who ended up getting the role of Heather may have been in the waiting room [when I auditioned].

Susan Mohun, Heather: I had a few different auditions, and I don’t think I’m supposed to name names, but my final audition was with Paul Rudd and a famous actress’s daughter who seemed to be very good friends with Amy Heckerling. I had a 104 fever and had gone in the hospital, but decided I was just going to go for the heck of it to the final audition. I was sure that I wasn’t going to get it because I was really sick, and this other girl, who looked exactly like her very famous mother, seemed to have it in the bag. So that was a surprise to get the role—and very exciting.

I didn’t realize, obviously, that 20 years later we’d be talking about it.

Paul Rudd: After the table read we all went and got a bite to eat. We went to a place not far, around the corner, that I used to go to, which was kind of a bar. They probably should not have let some of those kids in. I do remember all of us sitting around saying, “How cool is it that we’re all going to do a movie about kids our own age?” And having that conversation about the John Hughes movies to our generation. It had been a while since there was one of [those]—“How cool would it be if this thing had legs?”

Then it kind of did.

The Critical and Box-Office Success of Clueless