10 Things I Hate About You (1999 Film) | It Shouldn’t Work


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Feb 27 2025 64 mins   2

With his directorial debut, Gil Junger delivered an iconic romantic teen comedy with his adaptation of the controversial Shakespeare classic, “The Taming of the Shrew” that probably shouldn't have worked. In episode 337, join Luke Elliott & James Bailey as they react to the moment that audiences fell in love with Heath Ledger, explain the Julia Style poem’s connection to the Kendrick/Drake feud, appreciate the screenwriting skill on display, talk about the Clueless inspiration, and finally cast their votes on which is ultimately better: the book or the play?

Luke Elliott

James Bailey

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