#219 | 10 Things I Hate About You

From Clueless to Cruel Intentions, to She’s The Man and She’s All That, many 90s and early 00s teen rom-coms drew heavily from classic plays and literature. The results were predictably varied, but alongside Clueless, 10 Things I Hate About You represents the genre at its peak.

Loosely based on Shakespeare’s The Taming of the Shrew, what 10 Things I Hate About You lacks in Clueless‘ subtle intelligence, it more than makes up for in charm and a wholehearted commitment to absurdity.

The cast is stacked with future stars including Julia Stiles, Joseph Gordon Levitt, Gabrielle Union and the late Heath Ledger in his first major US movie role. In recent years, the actors have spoken about the strong bond they formed on-set, and this sense of fun shines through and really elevates the movie.

Ledger and Stiles in particular shine in their roles as the antisocial high-school outsider and the slacker who accepts a bet to win her heart, only to [SPOILER ALERT] fall in love with her for real. Ledger’s song and dance routine to Andy Williams’ Can’t Take My Eyes Off You is an instantly star-making scene which melted the hearts of a generation of teenage girls (and some boys), while Stiles briefly threatened to become her generations’s Winona Ryder and it’s honestly kind of a shame that it never quite happened for her.

In this week’s podcast, we break down some of our favourite moments from the movie, including Allison Janney’s hilariously unprofessional Guidance Counsellor, the strangest game of paintball we’ve ever seen and the iconic arrival of Nigel with the Brie. We also come up with some drinking game ideas, check in with our listeners and pitch sequels to catch up with this charming cast – sadly minus Ledger – over two decades later.

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Next time, we’ll be exploring a micro-genre we haven’t really touched before, inspired by Harry’s enduring love of films that get future technology hilariously wrong. Until then, happy listening and remember – in real life very few successful relationships begin with one partner dating the other one in order to fulfil the terms of a bet…