'Clueless' Director Reveals 10 Secrets You Didn't Know

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"What good is that if the people go, 'Isn't it nice they remember?' and you go, 'I wish it would have helped me do other things because it's f—ing hard,'" Amy Heckerling tells THR of wanting the now-beloved film to have performed better at the box office.

Reese Witherspoon, Dave Chappelle and the Beastie Boys' Ad-Rock in Clueless? As if!

With the seminal 1995 teen comedy marking the 20th anniversary of its release on July 19, writer-director Amy Heckerling spoke to The Hollywood Reporter about her lasting memories of making the film. This includes the fact that Witherspoon came quite close to nabbing the role of matchmaker Cher, which became a career-defining part for Alicia Silverstone

Here are 10 things you may not know about the film's sometimes-bumpy production, including every studio passing on it, the script constantly undergoing changes from the set and Heckerling's mixed feelings about the fans who have more recently fallen in love with Clueless.

It started out as a failed pilot

Clueless began its life as a TV pilot for 20th Century Fox, with the company encouraging Heckerling to write about "the cool kids" at a high school rather than "the outsiders," which writers typically focus on. Heckerling penned the TV script using the same tone and many of the characters that would later appear in the film, but Fox eventually passed and Heckerling soon switched agents. "Everything was going to hell," she remembers.

Fox wanted more of the guys — and didn't think stepkids should get cozy

Heckerling landed at CAA, where agent Ken Stovitz decided the pilot was "too good for TV" and needed to be a film. So they took it to Fox's film department, and the execs liked it but wanted the script to "be geared more towards the [male characters], and I had problems with that," Heckerling says. 

Another sticking point with Fox was the fact that Cher and love interest Josh (Paul Rudd) were stepsiblings. "[Fox execs] said, 'Oh, it would be like [if two characters on] The Brady Bunch [were dating],'" Heckerling remembers. "They thought [Josh] should be her neighbor," which reminded her too much of Meet Me in St. Louis.

Ultimately, with teen-oriented comedies like Airheads and the Jeremy Piven-starring PCU underperforming, Fox got gun-shy and put the script in turnaround.

No one was interested — until Rudin came to the rescue

"Everybody in town said no," Heckerling says about the response she got from the other studios. Finally, Stovitz got the script to producer Scott Rudin. "When Scott said he wanted to do it, then all the people who wanted to pass had a bidding war over it." Rudin encouraged Heckerling to bring the script closer to how she had initially envisioned it, before the various sets of notes had been implemented.

Casting craziness — and Reese as Cher?

There are rumors about numerous now-A-list stars having read for roles, including Angelina Jolie, Ben Affleck and Terrence Howard, but Heckerling doesn't quite remember all of those big names having sat down with her to audition. She does confirm that Reese Witherspoon was a contender to play Cher. "She had such a strong personality and sense of self," the director says. "[But] she would have to act Cher — Alicia was Cher."

Dave Chappelle came very close to nabbing the role of Murray, which eventually went to Donald Faison, but Chappelle already seemed a bit too mature for the part. "He was just amazing — he was such a mensch," Heckerling says, but "I needed somebody who was really innocent, a goofy kid."

Heckerling refers to the role of Josh as the toughest to cast. "[While I was writing,] I was thinking of Adam [Horowitz] from the Beastie Boys as what the guy looked like," she continues, pointing out that "Paul [Rudd] was perfect."

Constant script changes

The shooting script didn't undergo major alterations once production began, but lines were constantly getting tweaked on the set, with members of the cast and crew feeling comfortable to make suggestions. "Every day there were changes," Heckerling remembers, adding that the phrase "going postal" was pitched by a crew member. "If Donald Faison wants to say he's keeping it real, you're going to go with it," she says, referring to a line that the actor ad-libbed.

Brittany Murphy was "such a sweet girl"

Heckerling has fond memories of working with Brittany Murphy, who played newcomer Tai. "She was the youngest [of the main cast], and it was a whole new world for her," Heckerling says. "She's such a sweet girl, and she brought such a fun, quirky, endearing quality to the part. I love her, and everybody misses her so much."

Oscars snub after a category-change snafu

Heckerling's script earned her a Writers Guild Award nomination, and she was hoping for an Oscar nom as well, but it sadly didn't happen. "Ninety-nine percent of the things nominated for the Writers Guild are nominated for Oscars because it's the exact same people [who] voted," she explains. 

However, the film landed in the best adapted screenplay category for the Oscars, as it was credited as an adaptation of Jane Austen's Emma. "Then, you have to compete with the real Jane Austen because [eventual winner] Sense and Sensibility [was nominated in the category]," says Heckerling, who is quick to mention that West Side Story is not credited as an adaptation of Romeo and Juliet. She also wishes that Paramount had put more of an effort into an awards-season campaign for Clueless

Hollywood is still a "f—ing hard" business, even if you made Clueless

Though Clueless is now beloved, Heckerling remembers that its opening weekend — $10.6 million for second place — wasn't seen as remarkable. "It wasn't a big hit, you know?" she says. "There were tons of rom-coms that you may not even remember that made as much or more." She explains that the film was perceived as geared toward female audiences, meaning "you're still in that ghetto."

She now has mixed feelings about people who tell her they discovered the film long after it left theaters. "[Right after it came out,] nobody's banging down your door, you're still struggling all the time. And then years later, [people latch on to the movie,] and it's like, 'Well, that would have helped earlier, little shit,'" she jokes. "What good is that if the people go, 'Isn't it nice they remember?' and you go, 'I wish it would have helped me do other things because it's f—ing hard.' But what are you going to do? Is it better to be everybody's darling, and then they don't like it later? I don't know."

Turning into a musical

Cher and the gang could soon live on in a theatrical production, as Heckerling is developing a musical version with producers who worked on Jersey Boys and The Who's Tommy. "I wrote the book and lyrics," Heckerling says. "We're starting to beat out numbers with some music supervisors." 

Regularly hanging out with her stars

Heckerling, who says she's "never been happier" on a film than she was while working on Clueless, stays in constant contact with the cast, including meeting up with Rudd recently while he was taking a break from his Ant-Man shoot. "I love all of them," she says of her cast.

Email: Ryan.Gajewski@THR.com
Twitter: @_RyanGajewski