Episode 934: Medium, Medium, Medium, Can’t You See?

On the Overthinking It Podcast, we tackle modern classic “10 Things I Hate about You,” based on an Early Modern classic by Shakespeare.

by Matthew Wrather
June 1st, 2026

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Pete Fenzel, Mark Lee, and Matt Wrather follow their discussion of Zizek’s theories of cinema and desire to a definitive practice of cinema and desire, the late 90s teen romcom classic, Ten Things I Hate About You. Discussing a movie that not so much “holds up” as “remains excellent despite its deplorably cringe rap scene,” the three celebrate the movie’s craft along with its art, breaking down its style of iconic visual storytelling that make its comic types alongside its heartfelt leads feel resonant and effortless.

Recapping the key structural expectations of 16th and 17th century theatrical moralizing and the ways Shakespeare’s Taming of the Shrew falls shorter than short by modern standards (mostly around gender), the three delve into how Ten Things strives to rebuild a classic the way it should be, while running into its own lampshaded moral inadequacies, also characteristic of its time (mostly around race).

But even that fails to undermine legendary work by an all-star cast, led by immortal turns by Heath Ledger and Julia Stiles. Sometimes you write “iconic” more than once because it is the best word for the situation. As too are the film’s wall-to-wall needle drops.

All that plus consideration of hot-tub-as-luxury, and also balcony-as-luxury, not to mention that great yonic privilege indicator: hot-tub-on-balcony-as-luxury, which may or may not have been all that expensive 27 years ago. But this podcast is not “10 things I hate about inflation.” That’s every other podcast.

For your own challenge, join us on the Discord with your own version of Shakespeare’s Sonnet 141: “In faith I do not love thee with mine eyes.” And see if you can one-up a fictional 90s high schooler and write an actual sonnet.