How Amy Heckerling Made The Classic “Clueless”: 52 Weeks Of Directors

by Lauren C. Byrd

Amy Heckerling grew up in the Bronx and then Queens and attended the High School of Art and Design in Manhattan. She wanted to be a writer and artist for MAD Magazine but changed her career goal when she saw what the boy next to her had written for his goal. He wanted to be a film director.

“I was really annoyed because I thought that if an idiot like that guy could say he wanted to be a director, then so could I, and certainly I should be a director more than he should. It had never occurred to me that that was a job possibility. He put the thought in my head because until then I would have never thought of saying that I wanted to do that; it didn’t seem to be one of the jobs in the world that could be open to me,” Heckerling said in Breaking In, a book of interviews with 20 film directors about how they got their start.

Amy Heckerling directing

Heckerling had been interested in movies and storytelling since she was young. She grew up in an apartment building full of Holocaust survivors. “Most of them had tattoos on their arms and for me there was a feeling that all of these people had a story to tell,” Heckerling said.

She spent time watching films and television with her grandmother. Her favorites were gangster movies, musicals, and comedies.

After graduating from high school, Heckerling attended NYU’s Tisch School of the Arts to study film. She had to take out a large loan to cover her expenses, which she has said added stress to her life. During her time there, Heckerling made musicals. “It was the mid-70s and it was a bizarre combination of long hair with bell bottoms. With this, I sort of infused a 1930s idiotic grace that didn’t go with the post-Watergate mentality that was prevalent at the time.”

Heckerling followed her friend Martin Brest to the American Film Institute in Los Angeles for graduate school. She felt there would be more opportunities to break into the industry, but she experienced severe culture shock after moving from New York to Los Angeles.

Amy Heckerling headshot

Her first job was lip-syncing dailies for a television show and she started making connections in the business. In her second year at AFI, she made her first short film, Getting It Over With. The film was about a girl who wants to lose her virginity before she turns 20. After graduation, Heckerling continued to work on the film. She tried to use the film to get a job, but Tom Mount, the president of Universal Pictures, said she would have to get an agent before he could hire her. After struggling to find an agent, Mount called Heckerling and asked her to make a film.

Heckerling’s first feature was Fast Times at Ridgemont High (1982) which was based on the observations of Rolling Stone journalist Cameron Crowe. Heckerling read Crowe’s book and worked with him on rewriting the script because she believed there was too much studio interference. The film launched the careers of numerous stars such as Jennifer Jason Leigh and featured appearances by several actors who would go on to become stars, like Nicolas Cage, Forest Whitaker, and Anthony Edwards. The most notable role in the film, however, was Jeff Spicoli, played by Sean Penn, which rocketed Penn to fame.

However, the studio was unsure of how to market the film. Universal opened it in a few hundred theaters on the West Coast with no advertising. But upon opening, the film was a huge success, so the studio opened it at theaters across the country. The film earned $27 million at the box office and Heckerling wrote, directed, and produced a TV series for CBS based on the film.

Amy Heckerling directing black and white photo

After the success of Fast Times, Heckerling received numerous scripts about similar subjects: high school, preppy kids, or girls losing their virginity. Instead, Heckerling’s next film was Johnny Dangerously (1984) which starred Michael Keaton and was a spoof of gangster movies. The film was a flop at the box office but has since become a cult hit.

The next year, she directed National Lampoon’s European Vacation. Heckerling became a regular at the studio level, moving on to write and direct Look Who’s Talking and its sequel, Look Who’s Talking Too. She said she loves writing comedies because she says since everyone is going to work on this film for more than a year, she wants the time to be happy and fun.

“I wanted to have hits the way boys had hits, not like a ‘girl hit’ that made $50 million, but a boy hit that made 100s of millions,” Heckerling said of her goals. Look Who’s Talking earned $296 million at the box office.

Amy Heckerling and Chevy Chase

In 1995, she wrote and directed Clueless, a modern teen comedy that reworked Jane Austen’s Emma. The film features wealthy teenagers living in Beverly Hills. To research the script, Heckerling sat in on classes at Beverly Hills High School. However, she observed that the students did not dress in high fashion every day and would dress frumpily as everyone else. The film and its characters caught on with teenagers and became a significant pop culture reference point, particularly for kids who grew up in the 90s.

Clueless, like Fast Times, was spun off into a TV series. Heckerling penned the pilot and directed several episodes.

In her 2007 film, I Could Never Be Your Woman, Rosie, played by Michelle Pfeiffer, is a writer and producer of a similar TV show about a teenage girl. Rosie, like Heckerling, is a single mom to a pre-teen daughter (Saoirse Ronan). She falls for a younger guy—played by Paul Rudd—who gets cast in the show, but Rosie worries she’s too old for him and convinces herself he’s only interested in her as some kind of career move. Meanwhile, Rosie battles the network bosses—all guys—to keep control over her show and keep it on the air.

Michelle Pfeiffer and Paul Rudd in I Could Never Be Your Woman

When asked how much of the film is taken from her personal experiences, Heckerling told The A.V. Club, “Some of it. Mainly the idea of having to try to figure out what’s going on with the youth of today, and then trying to cater to them and serve them up something you know is BS, because you have a real young person around you.”

still from I Could Never Be Your Woman

Sadly, due to financial troubles with some of the film’s backers, I Could Never Be Your Woman sat in limbo for several years and never made it to theaters. Ultimately, it was released straight to video. At the time, Heckerling was also caring for her parents, who were very ill, and had to choose her battles. Although she was disappointed about the film not being released theatrically, she says she enjoyed making the film and working with Pfeiffer, Rudd, and Ronan.

Although the film uses a quirky framing device in which Tracey Ullman plays Mother Earth who preaches the ridiculous standards of beauty used by the media and particularly by Hollywood, the film does have a good commentary on beauty and age standards and both Pfeiffer and Rudd are clever and charming in their roles. Ronan, who is at the point of pre-teendom where she has to decide whether to be true to herself or give in to societal expectations of what it means to be cool, infuses her character with a sweet naiveté.

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