Feature films
Heckerling's first feature was Fast Times at Ridgemont High (1982), based on the non-fiction account of a year in the life of California high school students as observed by undercover Rolling Stone journalist Cameron Crowe. When Heckerling first signed on to do a feature for Universal, she read a lot of scripts, but it was Crowe's script for Fast Times at Ridgemont High that stood out to her. Although she loved the script, she felt that it bore the marks of excessive studio interference, so she read the novel, determined which parts were strongest, and sat down with Crowe to rework the script. The film helped launch the careers of numerous stars, including Jennifer Jason Leigh, Judge Reinhold and Phoebe Cates.
In addition, it marks early appearances by several actors who later became stars, including Nicolas Cage, Forest Whitaker, Eric Stoltz, and Anthony Edwards. Most notable, however, is the appearance of Sean Penn as Jeff Spicoli, who was launched into stardom by his performance. Heckerling describes casting Penn, whom she first met while he was sitting on the floor outside of the casting office, as a feeling of being overwhelmed by his intensity, even though all he had done was look up at her. She knew that this was her Spicoli, even though they had seen other people who had read better for the role. Ally Sheedy read for the role of Leigh's character Stacy Hamilton, but Heckerling decided that she wanted someone that seemed younger and more fragile (though Jennifer Jason Leigh is more than four months older than Ally Sheedy).
Heckerling was discriminating about the film's soundtrack. Originally, the film was supposed to have music in it by bands like the Eagles. "I guess a lot of people like that stuff, but being young as I was at the time, I really wanted a new edgy eighties music soundtrack. I wanted Fear, Oingo Boingo, The Go-Gos, Talking Heads, and the Dead Kennedys. I was one of those obnoxious teenagers that thought that the music I liked was great and everything else sucked. Getting that Oingo Boingo song in the film was a big fight. But I had to make some compromises and put in some songs that I didn't like at all."
The studio was unsure of how to market the film, and Heckerling guesses that they did not think that anyone would want to watch it. The studio decided to just open it in a few hundred or so theaters on the west coast without any advertisement. Once the film opened, it was a huge success, leading the studio to quickly open it at theaters around the country. It became an instant hit right out of the gate, eventually going on to become a pop culture touchstone. The film earned $27,092,880 at the box office in the USA. It also spawned a short-lived series on CBS called Fast Times, with Heckerling writing, directing and producing.
After doing Fast Times at Ridgemont High, Heckerling was bombarded with similar but lesser scripts. It was hard for her to find anything that wasn't about high school, preppy kids, or a story about a girl losing her virginity. Eventually she found her next film. Johnny Dangerously (1984), with Michael Keaton, Joe Piscopo, Danny DeVito, Dom DeLuise, and Peter Boyle, was an Airplane!-style spoof of gangster movies, but it failed to catch fire at the box office upon its initial release. Heckerling attributes the film's failure to the public's lack of familiarity with the gangster movies that the film was poking fun at. "It was pure satire of something nobody remembers. I think that was the main problem, because all the actors and writers did great jobs. But we were definitely satirizing something ... I mean, unless you watch 1930s movies on TV at night, people don't remember. Somebody told me that during a screening they were sitting next to Brian De Palma, who had just done Scarface, and he was in hysterics. If you studied those movies, you know what we were doing." In subsequent years, however, it has garnered a substantial cult audience.
The following year, she directed National Lampoon's European Vacation (1985) with Chevy Chase and Beverly D'Angelo, a sequel to the popular National Lampoon's Vacation. With it, Heckerling scored her second solid hit, earning $74,964,621 at the box office. The film, like many of Heckerling's films, received poor reviews from critics but proved to be very popular with audiences. Heckerling, despite being well educated and loving the work of such intellectual writers as Franz Kafka, has admitted that she loves "silly things," which has proven to make her commercially successful in the comedy genre.
In 1989, Heckerling had her biggest success with Look Who's Talking, starring John Travolta, Kirstie Alley and a baby voiced by Bruce Willis. Heckerling got the idea for the film while she was pregnant with her daughter and developed it into a feature. Heckerling says that she loves to write comedies, such as Look Who's Talking, because she notes that when a film is made, everyone working on it puts more than a year of their lives into making it, so she wants that year to be happy and fun. Heckerling, who loved Travolta, was ecstatic to work with him, though many people consider the film's release to be during the end of a low point in Travolta's career. The film has been Heckerling's highest-grossing film to date, earning $296,999,813. After the film's release, Heckerling was able to cross off the second of two goals that she had set for herself in college, the first being to make a studio feature, which she did with Fast Times at Ridgemont High, and the second being: "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."
Two Look Who's Talking sequels would follow—1990's Look Who's Talking Too—also directed by Heckerling and co-written with her then-husband Neal Israel. The film added another baby to the storyline and was a moderate success. Heckerling then produced, but did not direct, the third and final sequel, Look Who's Talking Now—a flop. The films also spawned a brief television show called Baby Talk, although Heckerling had little involvement.
In 1995, she wrote and directed Clueless, reworking and updating Jane Austen's Emma as a 1990s teen comedy about wealthy teenagers living in Beverly Hills. Heckerling originally thought of Clueless as a television show, because she loved to write the character of Cher, who she saw as a "happy, optimistic, California girl", and wanted to explore all of her adventures, but after she pitched it to her agent she was told that it would make a great feature. To research for the script, Heckerling sat in on classes at Beverly Hills High School where she observed how teenagers acted, although she admits that most of the movie script was made up. She notes that teenagers at the high school did not dress in high fashion every day as the characters do in the film; in reality the students there dressed just as frumpily as everyone else. She did, however draw on many of her observations, especially the tendency of teenage girls to groom themselves constantly. "You would think that within, you know, the few minutes that they've been in class, that their makeup wouldn't be needing so much repair and yet they're constantly painting and sculpting and ... doing to themselves."
As with Fast Times at Ridgemont High, it quickly caught on with teenagers and went on to become a significant pop culture reference point. The film went on to gross $56,631,572 and helped launch the careers of most of the cast, including Alicia Silverstone, Brittany Murphy, Paul Rudd, Donald Faison, Breckin Meyer, and Stacey Dash. It was spun off into a moderately successful TV series, with Heckerling writing the pilot, and also directing several episodes from the first season. She described the show as basically the same as the film, only cleaner, and says that she still loves the characters.
Heckerling directed and produced Loser (2000), a romantic college comedy with Jason Biggs and Mena Suvari. The film was not a critical or commercial success. After a break, Heckerling's romantic comedy I Could Never Be Your Woman (2007), starring Michelle Pfeiffer and Paul Rudd, never opened in theaters; rather, it received a direct-to-video release domestically, despite fairly good notices. Production of the film was troubled by financial issues, including the rights to distribution being sold off without Heckerling's knowledge, making it difficult for her to sell the film to a studio. At the time, Heckerling was also taking care of both of her parents who were very ill (her father was in the hospital and her mother had cancer). Though Heckerling disliked the baggage that the film carried and was upset about it not being released theatrically, she says that the experience was significant for her because she loved working with Rudd and Pfeiffer in England. Heckerling also directed an episode of the NBC version of The Office.
In 2011, Heckerling directed the horror-comedy film Vamps with Sigourney Weaver, Alicia Silverstone and Krysten Ritter, about two vampires living in New York City as best friends and roommates. The film was released to theatres on November 2, 2012, followed by a DVD release on November 13. On July 4, 2016, Gilbert Gottfried posted an in-depth 81-minute interview with Heckerling on his podcast. In July 2017, a musical version of Clueless helmed by Tony nominee Kristin Hanggi received a developmental lab in New York City. A previous workshop starring Taylor Louderman (Kinky Boots) and Dave Thomas Brown (Heathers) took place in 2016. Heckerling wrote the libretto for the musical. The musical opened Off-Broadway on November 20, 2018 with Dove Cameron in the lead role.
