Totally 'Clueless': Director Amy Heckerling and star Elisa Donovan dish about making the 1995 coming-of-age classic

When Clueless hit theaters on July 19, 1995, the female-led coming-of-age comedy became the ultimate whatever to everything else happening in the world.

Director and writer Amy Heckerling introduced us to a new wave of young Hollywood stars — Alicia Silverstone, Paul Rudd, Brittany Murphy, Donald Faison, Stacey Dash, Elisa Donovan and Breckin Meyer — who (mostly) played indulgent, image-conscious, label-loving Beverly Hills teens. Dressed in trendsetting fashions, spitting soon-to-be iconic slang and set to a killer soundtrack, Clueless quickly became a pop culture touchstone.

Heckerling, who was already known for comedy hits Fast Times at Ridgemont High, National Lampoon’s European Vacation and Look Who’s Talking, crafted a satirical take on the high school superficiality in the famed 90210 ZIP code. Loosely based on Jane Austen’s classic Emma, it captured teen angst of the ’90s variety.

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At its center were best friends Cher (Silverstone) and Dionne (Dash), “named after great singers of the past who now do infomercials,” and their family, friends, crushes and teachers. Heckerling expertly observed and preserved pop culture references from that time, name-checking stars like Marky Mark, Pauly Shore and Luke Perry, and infusing things like Mentos and Noxema commercials, fluffy pens, Beamers and berets into the script.

For Clueless’s 30th anniversary, Yahoo takes a trip back with Heckerling, 71, who gave the film its unmistakable female voice, perspective and humor, and Donovan, 54, who played Cher’s fabulous frenemy Amber: the redhead with a budget-blowing wardrobe, plastic surgeon on speed dial and some of the film’s best one-liners for exclusive conversation about their Bronson Alcott High School days.

Crafting the perfect script, from Caboodles to catchphrases

To tap into the headspace of a Beverly Hills teen, the NYC moviemaker, then in her 30s, observed high school students, absorbing the culture.

Heckerling: I went to different schools, but a [teacher] they let me hang out a lot with was Herb Hall, who was in charge of the drama department and taught a debate class [at Beverly Hills High School]. He’s in the film as the principal. He was wonderful because he had a sense of humor, but was trying his hardest to get through to [the students]. ... You’re seeing them [in class] with Caboodles [makeup kits]. I would be like: I can't believe they're doing their grooming the whole period… My teachers would have come by with a ruler, banging on your desk: “Put that away."

Director and writer Amy Heckerling defined a generation with Clueless ... but whatever. (Alan Chapman/Dave Benett/Getty Images)

The film provided a dictionary's worth of new slang that came from Heckerling’s world.

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Heckerling: Some of my lesbian friends would say “as if” all the time, and then it got shortened to “ziff.” They also said “whatever” — and then if two people put their arms up together, making a big “W,” that was a big whatever. So I owe that to a few friends. Also, one day there was a Barbra Streisand special and I had HBO and they didn't. They said, “Can we come over and watch it [and] invite some friends?” I said, “Yeah.” So I'm upstairs writing, and they’re having a party in the living room and kitchen, and they start to play this game, “Suck and Blow.” I was never a cool kid … and you go: What are they doing?

The original studio pushed back on Heckerling’s female-driven story, but a new home embraced it and brought the film to life.

Heckerling: Once we were at Paramount, and had [CEO] Sherry Lansing and [producer] Scott Rudin, it was cool people making the film. I was in the clear. When I was at the other studio … they didn't want to make a movie about female protagonists. … They wanted to make sure the boy characters were bigger than the girls. … Fortunately, we wound up somewhere else.

One of Heckerling's favorite scenes was the one where Dionne and Cher were talking to each other on their cellphones, saw each other but didn't hang up because it was "just silly." (Paramount Pictures/Getty Images)

Building a dream cast of Betties and Baldwins

Queen bee Cher was cast after 16-year-old Silverstone appeared in the first of three Aerosmith music videos.

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Heckerling: When I saw [1993’s] “Cryin’,” I went: That's her. I had this image that she would be what Americans consider perfect — certain body type, hair color and this idol we all have in our brain. Well, not all of us. I felt people would love her, but there's something so vulnerable and sweet about her. So I wrote the script and by the time I finished, there was the [music] video “Crazy” [with Silverstone and Liv Tyler]. So I videotaped it, handed in the script and the videotape, and the studio … said: [Steven Tyler’s] daughter? I was like: “No, the other one.” So [Liv] got Empire Records, and we got [Alicia] for Cher.

Heckerling with her cast: Justin Walker (Christian), Donovan, Brittany Murphy (Tai), Alicia Silverstone (Cher), Jeremy Sisto (Elton), Stacey Dash (Dionne), Wallace Shawn (Mr. Hall), Paul Rudd (Josh), Breckin Meyer (Travis) and Donald Faison (Murray) on set in 1995. (Paramount/Courtesy of Everett Collection)

The ensemble was built out slowly.

Donovan: It was a very long process. I first went in for [casting director] Marcia Ross in her office. I went back, again at Marcia’s office, for her and [coexecutive producer] Twink Caplan [who played Miss Geist]. Then I went to Paramount — and that’s the one I remember the most. It was in Scott Rudin’s office and I was petrified. It was the first time I'd been on the Paramount lot. ... [I was] trying to find his office and worried I was going to be late. The whole thing was overwhelming. It was Amy, Twink and Scott. Amy and Twink were just so warm and disarmingly like normal people. They didn't make me feel uncomfortable. They were sweet: “You're doing great.”

Elisa Donovan talks about stepping into Amber's shoes — and the memorable line that went over her head. (Storm Santos)

Murphy, who died in 2009, appeared in her breakthrough role playing Cher’s protégé Tai. The character was not modeled after Heckerling.

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Heckerling: No, everybody thinks that because she's got the New York accent … but that's just one part of things. The idea of who that Tai character is and what she's going through really comes from the Jane Austen Emma book, and Frankenstein, who creates something and it takes over. So, no, I would never tell somebody, “You're a virgin who can’t drive.” Whenever I see that scene, I get goosebumps with the way [Brittany] did it. That was like Invasion of the Body Snatchers … and certain Twilight Zones that were like suddenly — bang — they've taken over the soul and it's very frightening.

Thanks to Cher's makeover, Tai went from clueless to class queen, making things a little tense in the hallways. (CBS via Getty Images)

Rudd recently said that he almost blew landing Josh — Cher’s intellectual, college-age ex-stepbrother — because he buzzed his shoulder-length hair after his audition.

Heckerling: I really, really wanted [Paul]. We had a lot of people to go through, so I was still in the middle of casting. I'm not allowed to tell them: Oh, we want you. You're my first choice. You’re supposed to shut up because they have to make a deal for the agents. I learned that the hard way in my first film. So when I saw him [after his haircut], it was like: Ah! What did you do? I mean: I love you. I want you. [But] your haircut was perfect. It was like the cool kid. The outsider nerd. The smart boy.

Filming the future classic

While there were good vibes making the film, neither predicted Clueless’s lasting impact.

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Donovan: I felt like: Wow, this is amazing. This is how movies work. Women direct them. Women are in the power position. They hire all of the right people. They’re kind, generous and amazing at their job. I didn't understand how unusual all those things are. And I was so nervous about doing a good job. I was 22. It was my first movie and I didn't want to mess it up, so I was thinking about that rather than whether or not it was going to be a success. At the same time, you understand when something is working. It certainly felt like that. There was great chemistry and energy. I loved what I was doing. I loved my character.

Donovan believes that Amber's wardrobe was "part of her character." (Paramount/Courtesy of Everett Collection)

Heckerling: I'm always like: Was that OK? Is it funny? Do they look good? Is it telling the story? You want to get all those things in, all your ideas, and still make your day, because if you need more [shoot] days, especially [if a] female [director] needs more days, it’s like, What — did you get your period and you weren't working as fast?! All those pressures are on me. But with Clueless, I would walk onto the set and see where I was going to be shooting, and it was just beautiful. It was the colors that I wanted, the people wearing the things I wanted [under costume designer Mona May]. We had a genius cinematographer, Bill Pope. I told [set designer] Steve Jordan I wanted it to look like a fake imitation of Europe — fancy, but not quite real, like Hollywood's version of it — and he got it. It had that sense of humor, but prettiness. Then, seeing all my wonderful, beautiful actors, and I was like, Yay!

It all trickled down from an incredible script.

Donovan: Amy is a genius. She is. That script was the basis for everything. If you have a script like that, where it's on the page, it's just a joy, because it just informs everything, and then you get to put all of this depth into everyone. For Amber, I related to her in the sense that I definitely have my own sense of style that is unique, and sometimes it really works and sometimes it doesn't, but it's always my own sort of thing. But I didn't have the finances that Amber had. I was not flying to Paris runways and then bringing it to English class, which is what we would imagine she was doing. I based her on the not-so-nice girls I went to junior high and high school with, which also helped me to humanize them. I realized: These people just were feeling insecure. They just wanted to be liked. … I allowed [Amber] to be a little vulnerable, but that's where the meanness was coming from: She really wanted to be Cher's best friend, and Cher was not interested in that.

Even if some lines in the script went over the actors' heads.

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Donovan: The line I get most often today is “balls fly at my nose.” Truth be told, I didn't really get what that meant when I read it and there was a moment in the middle of shooting the movie where I went: Ohhhh, that's why everyone is laughing. I think it’s great that Amber didn't know because she just really wants to be loved — and, you know, be a little bit better than Cher at everything.

The premiere — and the paycheck

The premiere was in Malibu, Calif., in July 1995.

Donovan: I was working on Beverly Hills, 90210 and shooting that day, so [the studio] sent a limo for me. This is actually funny — I was the new guy on 90210. That day, they were rushing to get me out, and I remember the cast being like: Why is she getting picked up in a limousine? Where is she going? Who is this person? I was whisked off to Malibu, which was a very long drive from where 90210 was shot and I remember being in the limo by myself. I also didn’t know if I’d make it. I was late. The movie was almost over. I missed all the fun at the beginning and the photos, but I got to see pretty much everybody.

From left: Silverstone, Murphy, Heckerling and Dash on the sandy red carpet — which Donovan almost missed. (Getty Images)

Clueless was Donovan’s first big gig after playing Joey Lawrence’s love interest on Blossom — and she put her paycheck toward much-needed new wheels.

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Donovan: I got a car that functioned. I was driving a used Volkswagen Cabriolet that was so old. Sometimes the brakes would go out as I’m driving down Beverly [Boulevard]. I remember being like: Oh my god, oh my god. So I leased a new car [that] I was not in constant fear I might die in it. I got an Acura [Integra].

Heckerling didn’t make any big purchases. So, no Clueless closet?

Heckerling: Oh, no. If anything, I considered the way they were living a satire. I actually knew somebody who had that closet in the early ’80s. A very rich person. When I saw it, I was like: I gotta use this someday. This is just too weird.

What they took from the set — and the plot point fans won’t let go of

Heckerling: I have Brittany’s silver Doc Martens that she wore to the dance. They’re in my closet.

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Donovan: I didn’t get to keep anything. We just had an event at the [Academy Museum of Motion Pictures], and Alicia said she was allowed to keep a lot of [Cher’s outfits] but doesn’t know where they are. We were all laughing. I said, “I didn't get to keep anything, and you kept yours, and now you don't know what happened to them?!” I imagine people getting them at Goodwill or something.

Heckerling is aware that the film’s ending, in which Cher and Josh got together, got side-eyes.

Heckerling: People give me a lot of grief about stepsister, stepbrother, but it was Beverly Hills. People get married to a few people. At one point, [Cher’s dad Mel] was married to [Josh’s mom] and it was very short-lived. … But I like that [Mel] said, “You divorce wives, not children.” [Josh] has some of the love of [Cher’s] father, who she's very protective of, because that's her job and that gives her [importance]. Somebody is busting in on the affection, and that pisses her off, and he looks down at more frivolous behavior sometimes. So I thought: Well, that makes sense. Also, my grandparents were stepbrother and stepsister. In the ghetto in Europe, it was not uncommon. You didn't have the whole world, and you didn't go on swiping on your phone. It was a small community.

Josh (Paul Rudd) and Cher (Alicia Silverstone) were a case of opposites attracting. (Paramount/Courtesy of Everett Collection)

Forever Clueless — and that’s OK

They know the film will always be a prominent part of their résumés.

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Heckerling: It's awesome to see the cast. We don't all live in the same place, but we’re always in communication with texting. I [brought Clueless The Musical to London’s West End this year, writing the book] and had to do a lot of publicity for that … so we've been talking. Then they started with the 30th anniversary and the academy had a special screening. So I haven't shut up about [Clueless] for half a year. It's just amazing. I’m certainly talking more about it for now than I did at the time.

Clueless the Musical, also written by Heckerling, is finishing its run on London's West End. (Alan Chapman/Dave Benett/Getty Images)

Being tied to Amber forever is an association Donovan has grown to love.

Donovan: I've always felt very grateful because these are things that don't happen to everyone. I really look at it like a gift. That said, it’s a lot easier for me to say that now than 10, 15 years ago when you're trying to do other things and move on. It’s hard because no matter what you do, people … want to talk about [Clueless]. But something happened this year … where I realized: Wow, this film really has made an impact on people, and that feels very special, like a responsibility to have been a part of that. I feel super fortunate that I've been a part of so many of these things — 90210, Sabrina the Teenage Witch — that people really have strong connections to.

From Bronson Alcott to what’s next

Donovan is adapting her 2021 memoir, Wake Me When You Leave, into a film.

Donovan: I've written the screenplay and I'm attached to direct it. The film is in development, which means we have a partial cast, who are phenomenal, but we are trying to raise the financing for it. Independent films are labors of love, and so hard to get made right now. We’re really hoping and pushing, and I feel confident we will get there.

Heckerling has been busy with Clueless the Musical, which will begin a national tour of the U.K. after it closes in London on Aug. 23.

Heckerling: I've always figured out: How do I play the game and stay in, because staying in is hard for men, but really, really hard for women. … Whatever the new art form is, I want to be still in it. Whatever the new version of pictures and storytelling is and writing words for people to say — wherever it is, whatever it's on. I mean doing the show on the West End … and at my age… to do a new thing was really fun. I've done things that are streamed, TV and movies, but whatever's coming up. I don't want to be kicked out of the club.

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