Another teen comedy classic in the vein of Clueless, 10 Things I Hate About You has achieved cult status, and stands as one of the most beloved films of the 1990s. Coming in at the very end of the decade, it has a slightly more modern, and perhaps timeless, feel than Clueless. It too is a modern interpretation of a literary classic, this time from the Bard himself, William Shakespeare, The Taming of the Shrew. There are references to the source material dotted throughout (Bianca and Kat, Padua High School, etc), but as per Clueless, the film doesn’t stick too slavishly to the original. It captures the knowingly mischievous wit, but isn’t afraid to find modern alternatives.

The plot centres around Joseph Gordon-Levitt’s Cameron hiring Heath Ledger’s Patrick to date Julia Stiles’ Kat, so that he can himself date her sister Bianca (Larisa Oleynik). Their father has ruled that the younger Bianca can only date when Kat does, but Kat’s infamous misanthropy stands in the way of Bianca’s social ambitions. Kat abhors the idea of dating in high school, and with college on the East Coast beckoning and some classic literature to get through (we see her reading what else but The Bell Jar), she, quite understandably, looks down on the shallow nature of teen relationships and chooses to side-step them. Certified ‘bad boy’ Patrick Verona is the only man deemed ‘crazy’ enough to try to woo her. Surprise, surprise, what starts off as a job becomes a labour of love, and the film largely focuses on their burgeoning, if poorly founded, relationship. Dating people for money or bets seems to be a staple of 90s movies, but here it is handled with surprising complexity.

Kat speaks for a lot of us who have felt angry at a society that seeks to reduce us to our womanhood alone

Written by Karen McCullah and Kirsten Smith, the script offers a real sense of its characters, and a rounded interpretation of their motivations. Bianca is treated with unusual understanding – she is not simply dismissed as a shallow airhead. We see her trying to navigate difficult feelings and find a place in a world that seemingly only values her for her looks. Kat especially I think speaks for a lot of us who have felt confused and almost betrayed by our femininity at some point, and angry at a society that seeks to reduce us to our womanhood alone. It is no surprise that this script was written by women, as it shows real understanding of the experience of coming of age as a girl.

With Patrick and Kat, it is what she says that counts, not how she looks.

But the men are no less sensitively handled. Even comic-relief characters like sidekick Michael and Larry Miller’s father are cleverly written, with understandable motivations. Gordon-Levitt’s Cameron at times creeps into NiceGuy™ territory, adding a note of cynical realism. Heath Ledger’s Patrick is the standout. Slightly inexplicably maintaining his Australian accent, Ledger brings warmth and depth to a role which could easily have fallen into stereotypes. Beyond the exchange of money for dates, and some hijinks in class, we are never really given cause to think of him as the ‘bad boy’. This serves to justify his attraction to Kat: he is misunderstood and dissatisfied with the system too, even if in different ways. The fact that Kat is portrayed as a strong, independent, thinking woman, to whom he is attracted because of this, not in spite of it, is what makes their romance stand apart from the many others in teen movies of the time. Even Clueless’s Josh was considerably attracted to Cher by her looks. But with Patrick and Kat, it is what she says that counts, not how she looks.

With another iconic 90s soundtrack, Gil Junger crafted a specific yet timeless classic, which speaks to the complexity of the teen experience, presenting an exemplary directorial debut. The final product is hilarious and cheerful, but with greater depth and resonance than you might expect. It is surprisingly uplifting. If you want a teen movie that will entertain you but also get you thinking about the patriarchy (and when is that not the case?), this is the one to watch.

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Which do you prefer, Clueless or 10 Things I Hate About You? And what other movies do you think I should try that achieved similar levels of success? I’d love to hear your recommendations in the comments!