As both writer and director, Amy Heckerling ingeniously reworked Jane Austen's novel Emma for a modern day audience, giving a nuanced depiction of entitled teenagers while also satirizing teen films themselves. Heckerling cleverly modernizes the classic marriage plot, and sets it in the fast-paced, witty, sometimes vapid, always entertaining world of a Beverly Hills high school. The film was a smash hit, and solidified Heckerling's status as a master of the teen comedy. Having directed the cult classic Fast Times at Ridgemont High, Heckerling already had a reputation for skillfully depicting the subtleties of high school sociality, and so Clueless was a perfect choice for her.
Having recently found herself in some legal troubles surrounding the Look Who's Talking films, Heckerling was eager to write and direct her own movie. Clueless was that movie, perhaps the most rewarding project of her career. In an interview, Heckerling said, "That [Clueless] was the closest something in my head came to what was on the screen. I liked everybody in it, there was no aggravation, the studio left me alone and was supportive of selling it. It was just a great experience." The resulting film was a razor-sharp satire, beloved by both teens and adults.
While she shies away from talking about gender too explicitly in interviews, Heckerling is a feminist groundbreaker in that she is one of the few female filmmakers to have multiple box office hits. Heckerling depicts a multi-faceted perspective on femininity and gender in Clueless, and much of the authenticity of Cher comes from parallels with Heckerling's own life. In an interview in Interview Magazine on the topic of Tai's devastating line, "You're a virgin who can't drive," Heckerling says, "Well, that came from my self-doubt because I was the last American virgin. I didn’t know anybody who didn’t have a boyfriend when I still didn’t and I failed the driver’s test five times. These things make you feel like a loser. So to have somebody just hit you right where it really hurts…"