• Director: Amy Heckerling
  • Writers: Amy Heckerling, based on the novel Emma by Jane Austen
  • Starring: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd, Dan Hedaya, Elisa Donovan, Justin Walker, Wallace Shawn, Twink Caplan, Julie Brown, Donald Faison, Breckin Meyer, and Jeremy Sisto
  • Accolades: 2019 BBC Top 100 Films Directed by Women (#20)
  • Where to Watch: Stream with subscription on HBO Max, buy or rent on Amazon Video, YouTube, or Apple TV

At first glance, Clueless is another in a string of comedies in the 80s and 90s centering around vapid girls from Southern California, who spend their time obsessed with clothes and hanging out at the mall. These could be pretty dumb, but those that subvert the basic formula could often reach a sort of transcendence. Since its release (now 26 years ago!), Clueless has gained a reputation as something surprisingly smart and deep, especially considering the title. Writer/Director Amy Heckerling, whose prior successes included Fast Times at Ridgemont High, said that she was asked to do a comedy about teenagers. “I’m tired of teenagers,” she said. “I’ll only do it if I can make fun of them.” In the end, however, she can’t quite help finding flawed humanity in unexpected places.

For the plot of Clueless, Heckerling fairly straightforwardly lifted that of Jane Austen’s Emma, about a meddlesome rich girl who meddles a bit too much for her own good. Interestingly, this was the first film made of the book; Jane Austen didn’t really hit her stride as a modern cultural property until just about this time. Since then, Gwyneth Paltrow and Anya Taylor-Joy have headlined major, more straightforward productions. But Heckerling transplants the story to the high schoolers of 1995 Beverly Hills. Perhaps because of this, no movie has ever been more 1995, from the outfits to the slang to the soundtrack.

Alicia Silverstone plays Cher Horowitz, the bubbly blonde who is the most popular girl at her school and makes a hobby of matchmaking. She decides to make a project of a new, uncouth girl at school, Tai (Brittany Murphy). She disdains “high school boys” but soon becomes involved in her own romantic complications, while clashing with the only person in the story who acts like they’re on the same level as her, in the book the brother of her sister’s husband, but here her “ex-stepbrother,” Josh (Paul Rudd, in his first movie role). In a strange way, using one of Austen’s complicated plots makes there be more going on than in your usual high school movie, even a fairly good one like Mean Girls. And like Emma, Cher is unusually introspective for a young heroine. The real arc of the story is not that she finds love, though maybe she does, but that she decides that maybe she isn’t as good of a person as she thought she was and needs to work on herself.

Of course, this is probably overthinking it, since most of the fun of Clueless comes from it being, you know, clever and funny. For the movie that is credited with popularizing the phrase “As if!” this is a movie with a lot of surprisingly highbrow references. In an attempt to reassure Tai about a guy she likes dancing with another girl, Cher comments that the girl is a “Monet,” explaining, “from far away it’s OK, but up close it’s a big old mess.” During her date with a hot guy at school (Justin Walker), she finds that one of the “video tapes” he’s brought is Spartacus, because he’s “got a real thing for Tony Curtis.” We in the audience figure out way before she does that the guy is gay (or as her friend Dionne (Stacey Dash) puts it, he’s “a total Friend of Dorothy”), or at least we in the 2021 audience. I honestly don’t know how this would have played 1995, when Ellen DeGeneres was still starring in a sitcom where she wondered why she just couldn’t meet that perfect guy.

After a long, twisty production process, with a script that started out as a TV pilot (Heckerling called the first feature film draft I Was a Teenage Teenager) and a studio that kept insisting that the movie needed more prominent roles for the male characters, Clueless became something a sleeper hit. God forbid anyone ever make a movie about female characters, I guess, who would want to watch that? It has also stuck around in the zeitgeist far more than anyone involved likely suspected at the time, and it frequently makes lists with names like “The New Classics.” Its success spawned a TV series that I remembered as a flop but actually ran for 62 episodes, featuring the entire cast with the exceptions of Silverstone and Rudd. It also turned into a Broadway musical and a “collection of paperback books,” among other media.

Clueless also essentially launched the careers of a fleet of young actors, including Silverstone (who was previously known mostly for appearing in an Aerosmith music video), Murphy, Rudd, Breckin Meyer, Jeremy Sisto, and many others. I would certainly say that, if Clueless seemed in 1995 like the sort of movie you’d never choose to watch in a million years, it may be worth coming back to in 2021 because it remains loads of fun, and also remains a clear influence on a whole bunch of movies and TV shows that came after. The original role of Emma is a great part for younger actresses because it requires a particular mix of charisma and other, subtle emotions that seem like they would difficult to pull off. Anya Taylor-Joy is really great in the most recent movie version of the story. Here, Alicia Silverstone similarly gets the tone so spot on that it seems effortless, and it mains the role most people know her for. Anyway, I had a good time with this one.

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