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If John Hughes high school films carry a good amount of what I dislike watching in the sort, then Clueless is what I would cite as a perfect example of the high school movie done right. Amy Heckerling’s loose adaptation of Jane Austen’s Emma works on a count that not only is it one of these teen films by appearance, but also at how it’s poking fun at the sort of ideas that they present on the screen. It took me a second viewing to realize what it was about Clueless that I absolutely loved about it, for it had been years since I last came around to watching it. Amy Heckerling leaves behind not only a fun teen comedy, but a cultural staple for the 1990’s going down from both the fashion and the soundtrack, and an entertaining time capsule from start to finish. It can be referred to as a “chick flick” all you want it to be, but that doesn’t take the clever aspects of it away.

Alicia Silverstone playing  a 90’s re-imagining of “Emma Woodhouse” in Clueless.

Emma Woodhouse in this take on the story is a valley girl-type teenager by the name of Cherilyn Horowitz. Updating the setting to 1990’s Beverly Hills, it’s interesting to at least watch where Amy Heckerling is taking the story and tell it to another set of audience members, but it’s also fascinating to see how she is playing around with everything that forms a teen comedy. While it carries many of the elements that build a teen comedy, it still presents a great understanding of its source material and it transfers that sort of elegance which a Jane Austen story would suggest into a different period of time. Soon enough, it becomes clear that Clueless‘s use of the source material also becomes its greatest asset, for it also subverts the image it carries and turns it into something else entirely.

There’s no dispute to how Cher Horowitz is the valley girl stereotype, but the way that Amy Heckerling writes a character like her is why she stands out from the clique which she would fall under, taking what is already misguided inside of a John Hughes movie and being more self-aware about it. Amy Heckerling sets her up to be a personality we should dislike, but there’s a specific charm that comes from Alicia Silverstone’s performance that makes her immensely lovable. Cher, a mirror of Emma Woodhouse in the 20th century is a girl who does have good intentions for the people around her, but given the shell of what her character is supposed to be, it is also made all the better when Amy Heckerling’s writing puts her character in on the joke that was created by Clueless. As the title would suggest, it is common to refer to a valley girl as clueless about the world around herself, but Cher differs in the sense that she is a somewhat more knowledgeable figure in comparison to the many tropes of the stereotype, she is also unselfish, even with all the wealth she flaunts at others, and an independent figure, for she describes searching for a boyfriend as “searching for meaning in a Pauly Shore movie.”

Alicia Silverstone has never been better than she ever has been while she played Cher Horowitz, but also notable are the performances of the late Brittany Murphy and a young Paul Rudd. Brittany Murphy is yet another “clueless” figure that defines the film, as she starts out clearly unfitting into a new environment, then after meeting Cher who brings her in, gains a sense of identity. A young Paul Rudd appears in the film as Cher’s ex-stepbrother, and it’s nice watching how a young talent has started and eventually grown inside of his future – showcasing Amy Heckerling’s talent for discovering new stars and providing a good future for them as she had already done with Fast Times at Ridgemont High, a vastly different sort of high school film from this.

While Clueless certainly does follow a pathos that is not anything unfamiliar to the sort of comedy which it appears to be, it’s wonderful to see how Amy Heckerling’s writing is also very self-aware about these sorts of films, which is the key to its own effectiveness. The dialogue is only a small factor to Clueless‘s own wonder for it deconstructs the tropes that are already familiar for the stereotypes which it is portraying, but Heckerling’s own directorial eye gives the film a look of a regular high school comedy, only a small part of what makes it more fun to watch compared to many of the rest. She knows already how such characters are meant to act and behave, but Heckerling also gives these people a sense of development away from their stereotypes, giving them all such a lively feel.

Clueless is a girly film, no doubt about that, but when does a film being “girly” detract from its merits? Amy Heckerling takes what could easily appear as any ordinary high school comedy and turns everything around to show how misguided some of the most iconic examples can be (take Ferris Bueller’s Day Off for example, which I view as John Hughes’s best film of these sorts). It’s a time capsule that is very much reflective of the time period in which it came out, but if I were going to say that it is never entertaining to watch, I’d certainly be lying as Clueless always manages to get a smile out of me. But as Cher shouts, “As if!” As if there’s supposed to be any shame in me, a male, finding great enjoyment out of a film that would be deemed “girly” in some circles. It’s proof that high school movies can go beyond what they usually set out for.

Watch the trailer right here.

All images via Paramount.

Directed by Amy Heckerling
Screenplay by Amy Heckerling, from Emma by Jane Austen
Produced by Barry M. Berg, Twink Caplan, Robert Lawrence, Scott Rudin, Adam Schroeder
Starring Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd
Release Year: 1995
Running Time: 97 minutes