Film discussion

10 Things I Hate About You (1999) – Teen Movie Rewind

In our Teen Movie Rewind series, we explore coming of age stories and teen cinema, looking at the impact of the films themselves and the careers that they made.

As the 90s made way not only for a new decade but a new century, it was becoming clearer that Hollywood studios were turning to the classics with which to make new teen movies. 1999 had already seen the release of the Dangerous Liaisons-inspired Cruel Intentions to considerable box office success, while the decade had also seen modern interpretations of Emma and Romeo and Juliet.

The latter had been seen as being responsible for putting a new spin on Shakespeare that made The Bard’s work accessible to a new generation. Baz Luhrmann’s dazzling interpretation of one of Shakespeare’s most famous and romantic tragedies was responsible, along with Titanic, for making Leonardo DiCaprio one of the era’s most iconic heartthrobs while also giving Claire Danes her first big post-My So-Called Life performance.

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Shakespeare adaptations were everywhere towards the tail end of the decade and the century, and not just being remade into modern versions. As the 90s turned into the 00s, there would be modern versions of Hamlet and Othello, the latter modernised by Tim Blake Nelson and turned into O, while Kenneth Branagh was something of a one-man Shakespeare franchise, giving audiences more traditional interpretations of Much Ado About Nothing and Hamlet, but in a way that made them very mainstream and entertaining, even if he went all the way with Hamlet and delivered a four-hour version that while long was also incredibly well done.

A few months after the release of Cruel Intentions, 10 Things I Hate About You premiered, and with it, another modern version of a classic piece taught in English Literature classes. The Taming of the Shrew was one of Shakespeare’s most popular comedies, and like Jane Austen’s Emma, was more than capable of having its story brought bang up to date and refashioned into a teen romantic comedy. Nothing says 1999 like opening with ‘I Want You to Want Me’ by Letters to Cleo, and 10 Things I Hate About You does exactly that, beginning with pop-rock energy and never losing sight of its sense of pace and fun.

It’s also the biggest example of a 90s teen movie that would have a considerable impact when it came to launching the careers of its cast. Joseph Gordon-Levitt had already made his mark playing the youngest member of the cast of hit comedy series Third Rock from the Sun, but 10 Things I Hate About You was a clear example that he was capable of having a career away from playing child aliens on American television. Always coming across as someone with an inherent sense of decency in so many of his roles, both himself and David Krumholtz make for an entertaining double act in so many of their scenes.

Then there was Julia Stiles who came to the attention of so many with a brilliant performance that gave the film a sense of emotional groundedness. One of the joys of the story is the complete opposition of characters that Stiles’ role of Kat is in comparison to her sister Bianca, played by Larisa Oleynik who, similarly to Levitt, was making the move away from television where she had been playing Alex Mack.

Love and romance are recurring themes here, it is Shakespeare after all, and it’s something that every character in a Shakespearian rom-com must talk about, modern or conventionally, and the film does succeed in making Kat a determined character fuelled by feminism without sacrificing what makes her so interesting and three dimensional when she too falls in love. How hard is it though to resist Heath Ledger? It’s hard not to feel sad at his loss, even after all this time, not necessarily for the talent that was cut short, but also for the brilliance we may have gotten in the future.

For an actor who made his name in Australian teen shows, before making the move to Hollywood to star in brilliant pieces of froth like this and A Knight’s Tale, he would soon show that he was an actor of considerable range with powerhouse performances in Brokeback Mountain and The Dark Knight, the latter winning him a posthumous Academy Award for one of the most iconic and memorable performances in all of cinema.

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For a generation of teenagers growing up in the 90s, the key Ledger moment, and of the genre during that period in the late 90s/early 00s, was Patrick Verona, microphone in hand, serenading Kat with a full marching band in front of the entire school. It manages to be a moment that encapsulates everything unrealistic yet entirely wonderful about American High School set movies, where declarations of love can become epic and wonderful and funny and as romantic as anything the mind can concoct. For an actor whose performance as one of pop culture’s most famous villains is his most memorable, it’s easy to forget how truly versatile he was, going from romantic and genuinely funny lead in a film like this, to the deep emotional territory of Brokeback Mountain, to the cackling psychotic antics of The Joker.

On top of being one of the very best Hollywood teen films of the 90s, it’s also a reminder of just how brilliant an actor its leading man was and how much of a sting his loss still is after all these years.

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