Bird Watching – Amy Heckerling’s “Clueless”

In last week’s Top 5, Ben and John discussed their favorite teen comedies, which served as the inspiration for the film I want to discuss this week: the brilliant and hilarious Clueless, from writer/director Amy Heckerling. An earlier film directed by Heckerling, the Cameron Crowe-written Fast Times at Ridgemont High, made the cut on John’s list. But I truly believe Clueless to be her teen comedy masterpiece. There is probably not a week that goes by where I don’t quote this movie. If it’s on TV, I will be watching it. There are a dozen songs I can’t hear without thinking of it. I can’t see an actor from this film without being reminded of it and getting the urge to watch.  And god knows I am still fantasizing about that rotating closet.

So, we all know the basic story. (And really, if you don’t, if you haven’t seen this movie since it came out, or ever…just go away now. Go watch it. Seriously. Stop reading this.) Alicia Silverstone is Cher Horowitz, queen bee of her high school. Rich and beautiful, she appears at first glance to float along on a sea of superficiality and Diet Coke. But there is more to Cher than that, and her untapped desire to do good propels our series of adventures. After setting up two lonely teachers, hoping that a little romance will spread to them giving out better grades, Cher realizes that it’s not the chance for an unearned A that’s making her smile—it’s seeing that she’s done something that made someone else genuinely happy. Suddenly, the world is full of possibility. So, as part of their new do-gooder efforts (and being a bit unfamiliar with the concept of good deeds in general) Cher and her best friend Dionne (Stacey Dash) adopt the awkward new girl in school, Tai (Brittany Murphy), who is very unaware of how to present herself in order to get by in Beverly Hills, and commence making her popular.

In the grand tradition of “I’ve created a monster” kinds of stories, Tai’s newfound popularity ends up causing Cher more trouble than anything, as she herself begins to be eclipsed. Add in a couple of embarrassing romantic misadventures, an ill-fated night in the Valley that culminates in being robbed at gunpoint, and a stunningly failed driver’s test, and life has never looked worse for Cher. The only thing that’s going to save her: some serious self-reflection and some actual growth, on a path to leading a more sincere life.

This is really one of my favorite things about this film. Lots of teen comedies show their main character or characters going through a serious revelation, but all too often that comes so quickly—over the course of one day, even—that it doesn’t always feel like it will stick. This is an issue even in some of the greatest of movies—I’m thinking of Cameron deciding to face his dad in Ferris Bueller’s Day Off, or Claire admitting she hates doing what it takes to be popular in The Breakfast Club. The moments themselves are effective, but do we really believe that one day can make such a fundamental difference in a person’s life? This is the movies, so maybe that answer’s yes. But part of the beauty of Clueless and of Cher Horowitz as a character is that it takes her forever to figure anything out. And when she finally does—when fountains go off and she realizes who it is she loves and who it is she needs to be to get to the business of making herself happy—she still has a lot of work to do.

I’ll admit that a reason this film resonates so much with me (and with many of my friends) is simply because it was released at the perfect time for us. When I was 13, the VHS of Clueless was ubiquitous. Likewise, the movie poster adorned more bedrooms of girls I knew than ones it didn’t. Most 13-year-old girls wish they were 16-year-old girls, and envision that in just a few years, they’ll have the kind of glamorous life depicted in the film (or at least have a chance to make friends with girls who had that kind of glamorous life…more of us are Tais than Chers). Now, at 27, there is a part of me that still wants to live in the sunny world of these girls—shopping, driving convertibles, and waiting for the next cute boy to come along. I get to pretend a little bit, every time I watch the film.

Clueless is loosely based on Jane Austen’s novel Emma. While only the roughest skeleton of the film really stands up to the comparison, I have to say that I am all for contemporary updates of classic literature if they are done with the charm and skill seen here. Why not take a beloved literary heroine and put her in a context that’s more instantly accessible for young women? Any way we can get more three-dimensional female characters in big Hollywood movies is fine by me. Plus, even as a kid who was a big reader, there were plenty of novels and plays that I only got to after seeing an adaptation made me want to go back to the source. I still come across stuff that way, frankly. And there’s nothing wrong with it.

Everything about this film is enjoyable. Its quotability cannot be overstated, and the light satire of mid-90s wealth and frivolity holds up. I’ve focused here on the enduring appeal of Cher, and I do believe that she is one of the best main characters in the teen film landscape, written with piercing wit by Heckerling and played perfectly by Silverstone, full of warmth and heart. But all of the characters and actors are solid. The late Brittany Murphy is a comic revelation in her role as the ugly ducking turned Frankenstein’s monster. Has Breckin Meyer ever topped himself as slacker skateboarder Travis? Why didn’t Justin Walker, wonderful as Christian, turn into a big star? And, of course, it’s no secret how I feel about Paul Rudd. And the list of great actors could go on. Certainly, I could keep going on about all the fantastic details of this film. But I’ll sum up here. Clueless is a film that deserves a place at the head of the line when talking about teen comedies, or comedies in general, or feel-good movies, or literary adaptations, or movies made by women, or all of the above. It is smart, funny,  and fantastically rewatchable. It will simply always be one of my favorite films.


Brandi is one of those people who worries about kids these days not appreciating black and white films. She also admires great moments of subtlety, since she has no idea how to be subtle herself.

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