FemmeFilmFest21 Review: Clueless (Amy Heckerling)

Teenage girls are full of contradictions. Shallow and existential, audacious and anxious, convinced of their own importance and their own invisibility simultaneously, and capable of both incredible kindness and cruelty. As somebody who was a teenage girl not all that long ago, I can confirm that we do in fact contain multitudes, if anybody cares to look. Over the years, however, not many people have cared to look.

In mainstream film, teenage girls are easy punchlines, sex objects, or a plot device for some tortured father who needs the right motivation to get his act together. Drama sexualises or infantilizes them according to whichever is more convenient, and comedy laughs at them. For a while, the best a fictional teenage girl could hope for was to become a horror movie final girl. But even that had its own stringent requirements – have sex, and you’re immediately up for the cut.

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Of course, there were and are thoughtful portrayals – just look at the glut of compassionate dramedies centring teenage girls in the past decade. But these are a relatively new development and, in most cases, the exception to the rule. Besides, even these films largely take the slightly easier path of making their teenage girls misfits, the get-out-of-jail-free card of the teen drama.

Outsiders are easy to empathise with, even when they can be grating (as in Olivia Wilde’s fantastic teen-comedy Booksmart) or downright unlikable, but nobody has quite picked up the gauntlet thrown down years ago by one of, if not the best teen rom-com of all time: Amy Heckerling’s Clueless.

Adapted from Jane Austen’s Emma, one of many contemporary, teen-oriented reworkings of literary classics at the time, and follows Cher Horowitz, a girl who embodies all the contradictions a teenage girl can. She is equally kind and calculated, self-absorbed and selfless, both happily ditzy and the smartest person in most rooms.

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Cher takes new girl Tai under her wing as one of her many projects. Deciding to find her a more suitable match than Travis, the boy Tai actually has a crush on, and finds herself in a glorious tangle of relationships and miscommunications. Romance, shenanigans, and none other than Paul Rudd stars as the stand-in for Austen’s Knightley and Cher’s love interest – what more could an audience want?

On top of the tried-and-tested Austen storyline, Heckerling’s script is genuinely hilarious. Full of some of the most quotable one-liners of the 90s, and there is not a single weak link among the cast.

None of this, however, is enough to make Clueless stand the test of time. There have been hundreds of great, forgotten movies, especially in genres like the rom-com, which are more likely to be quickly dismissed. But here we are, twenty years later, still thinking about (and endlessly quoting) Clueless.

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It’s certainly not a movie designed to be disposable or frivolous, with a surprising amount of depth hidden just under the surface. Cher might be rich, beautiful, and clever, which Heckerling embraces, but she refuses to ever let this be the extent of Cher’s character. Emphasising her loneliness with the empty mansion she spends so much time in and the indifference of her classmates. She’s no Regina George or Heather Chandler.

And Heckerling complicates the fallacies other movies propagate about teenage girls who reject their richer and more beautiful peers, refusing to simply make another teen movie that reiterates adult ideas of what high school rich girls are like. There’s thought and precision here, as opposed to careless echoing of the movies that came before. 

On the other hand, perhaps Clueless is so memorable for the same reason the source of the story, Jane Austen, is still so widely remembered. As one of the original defenders of teenage girls in all their imperfect glory, Austen had a true understanding of all the overlapping contradictions at play in their relationships. Austen, in her novel Emma in particular, had a sharp, precise empathy for her characters, not only sympathetic to their good intentions and more than happy to skewer them for their occasional cruelties, but also fully aware of the sheer intensity of adolescence.

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There are no likable underdogs in Emma and Heckerling takes the same tack. The original Cher, Emma Woodhouse, was not quite a teenager, but as a sheltered young woman entirely enamoured with the world she had created for herself. She might as well have been, and would have likely been subject to, as much scorn as Heckerling’s Cher.

With no other experiences to widen their horizons, both Emma and Cher experience life and love in its full intensity. And Heckerling wisely adopts Austen’s empathy for that sheer magnitude of emotion.

Again, as a former teenage girl, while from the outside adolescent infatuations and heartbreaks might seem melodramatic, without the benefit of even just a few more years of accumulated wisdom, the intensity can be almost too much to bear. Instead of writing off their emotions as teenage histrionics (or even worse, female drama), Heckerling shows it for what it is, and treats every character with the sort of compassion that I wish more movies would show teenage girls.