‘Clueless’ turns 30: Jeremy Renner’s audition, Alicia Silverstone’s life-changing fax, and other surprising stories from iconic comedy

Could anyone really forget about Clueless, even three decades after its debut? As if!

Alicia Silverstone and writer-director Amy Heckerling joined costars and crew at the Academy Museum of Motion Pictures screening of Clueless on Saturday, marking the 30th anniversary of the iconic film’s July 1995 release — but it was Silverstone’s costars Breckin Meyer and Elisa Donovan who shared the biggest bombshells of the night.

Meyer, who portrayed laid-back skateboarder Travis Birkenstock, was eager to work with Heckerling, having been a fan of her earlier films such as Fast Times at Ridgemont High, Johnny Dangerously, and Look Who’s Talking. He also recalled some of the other actors who auditioned for the role.

“All the other guys I knew — Seth Green, Jeremy Renner, and all these cats — were auditioning for it,” Meyer said.

Donovan, who played Amber, the high school rival to Silverstone’s heroine Cher Horowitz, recalled one of her hairstyles in the film: Pippi Longstocking-style pigtails that required underwire architecture.

“There are pipe cleaners in there and then they braided around them,” Donovan said.

The teen comedy about Beverly Hills high school girls popularized infectious slang language like “I’m Audi,” “Baldwin,” and “total Betty.” Cher plays matchmaker to her teachers to make them go easier on her grades. But it makes her feel so good, she continues to try to fix up a new student, her makeover project Tai (Brittany Murphy). Unfortunately, her pick for Tai, Elton (Jeremy Sisto), falls for Cher instead.

If that plot sounds familiar, that’s because it’s based on Jane Austen’s Emma. One year later, Gwyneth Paltrow starred in a traditional adaptation of Emma.

“I started writing all these notes and ideas for this very happy girl that you just couldn’t burst her bubble, but I needed a plot,” Heckerling said. “So who’s ever written about a happy, optimistic girl? Fortunately, Jane Austen did. So I reread Emma and was like, ‘There is not one thing in here that could not work in Beverly Hills.’”

Silverstone did not read Emma prior to playing Cher. She only discovered the Austen novel after seeing a final cut of Clueless.

“It was fun to be able to identify all those characters and understand what she was doing,” Silverstone said. “It was so clever and I loved it.”

In the film, Cher goes to Bronson Alcott High School, at Heckerling explained the inspiration behind the school's name.

“Alcott was Louisa May Alcott’s father,” Heckerling said. “He was a free thinker and very progressive guy and he believed women should be educated, which they weren’t in those days. Louisa May Alcott wrote Little Women, and I was named after Amy.”

Heckerling also acknowledged her then-boyfriend, whose middle name is also Alcott. “I was seeing Bronson Pinchot,” Heckerling said.

Clueless almost never happened

When Clueless opened, Silverstone was best known for three Aerosmith music videos that played in heavy rotation on MTV, followed by a turn as a teen stalker in The Crush, the Dean Koontz adaptation Hideaway, and she had filmed many more yet-to-be-released films. But Heckerling shrewdly packaged her script with one of the videos.

“I saw Alicia in the "Cryin’" video and just said, ‘That’s the girl,’” Heckerling said. “I made a VHS tape, handed in the script and the tape. The studio I was at said no. That was Fox. So we were in turnaround. Then we went to all the other studios and they all said no. So that was just very depressing.”

Heckerling’s agent, Ken Stovitz, got it to Scott Rudin, then riding high at Paramount as the producer of hits like The Firm and Sister Act 2 and Addams Family films. With Rudin aboard, suddenly the studios were clamoring.

“When Scott Rudin liked it, there was a bidding war of all the people who hated it before,” Heckerling said.

Silverstone was in production on one of those other movies in Paris when she learned she would make Clueless when she came home.

“I remember when you sent me a fax,” Silverstone said. “Do you guys remember faxes? You sent me a fax saying, ‘It’s back on,’ because it had been gone for so long.”

The '90s were a fruitful time for Silverstone. As she went from job to job, she never anticipated Clueless would emerge as her most popular film.

“At the time, Clueless was my ningh film sort of back-to-back,” Silverstone said. “So I was tired. I just took it very seriously and thought of it as a job. I didn’t know what it was going to become. I was just doing a job with an incredible filmmaker. I’m in almost every single scene — maybe every scene.”

Getting into character

Clueless was a breakthrough for much of the cast: it was the first theatrically released film for Paul Rudd, with Halloween: The Curse of Michael Myers to follow that fall; Murphy, Donald Faison, Stacy Dash, and Sisto also had breakout roles. Casting director Marcia Ross looks back fondly at being able to discover so many rising stars in Clueless.

“It was a cast of all new faces and you don’t get to do that much anymore as a casting director,” Ross said. “It’s really hard today to find people that no one knows. It’s a credit to Amy because she can see the talent in all these people and also that the studio signed off on all of it. That does not happen today.”

Donovan said she based Amber on two mean girls from her high school, though would not name them despite Meyer’s goading. She also drew on an ex-boyfriend for Amber’s dismissive “whatever.”

“I actually had a boyfriend who was several years older than I was in high school,” Donovan said. “He used to say, when he was brushing me off, ‘Whatever, we’re not doing that. Whatever.’ It infuriated me so when I read this I was like, ‘Oh, I am taking back that word.’”

Meyer paid homage to previous cinematic slackers in his portrayal of Travis.

“I kind of just took Spicoli and Keanu [Reeves] from Bill & Ted’s and from Parenthood actually,” Meyer said. “In Parenthood, there was this thing Keanu did which was this very liquid shrug.”

Meyer learned to skateboard and ended up skating to his audition — out of necessity, not Method acting.

“I skated to my audition from North Hollywood over Highland to Paramount,” Meyer said. “If you know L.A. you never see a skateboarder there unless they’re dead. I didn’t have money for my car. I had a car but didn’t have money to put gas in the tank so I skated there. Doing Clueless, that let me turn on my heat in my apartment.  I didn’t have hot water when we made the movie.”

Playing a boy smitten by Murphy's Tai was easy, Meyer said. “Once she cast Brittany, how do you not fall in love with her?”

Cher’s iconic wardrobe with plaid skirts and knee-high socks was a stretch for Silverstone. Costume designer Mona May recalled Silverstone’s first fitting.

“Alicia, when you came into the fitting in your little sweatpants with the two dogs in tow, she was like, ‘What is this? I’m going to wear these binding clothes, really?’” May said.

Silverstone concluded the evening by noting that Clueless was her first comedy. After Clueless, Silverstone would star in comedies Blast From the Past, Beauty Shop, and TV’s Miss Match, among others.

“I didn’t know I was funny before that movie,” Silverstone said. “This was the first time I did a comedy because all those movies were very serious. I didn’t know that I could do comedy and that was really fun to find out.”

Fathom Events will rerelease Clueless in theaters June 29-30. Paramount Home Entertainment will release a 30th anniversary edition on DVD, Blu-ray, and 4K UHD July 8.