If there were a sequence of trigger words guaranteed to get millennials going, they would almost certainly include: Lena Dunham, Carly Rae Jepsen, and 10 Things I Hate About You. So when the news first broke that the Girls creator was teaming up with the princess of 2010s pop for a stage adaptation of the cult 1999 rom-com, which starred Julia Stiles and Heath Ledger, we elder millennials were wagging our tails like golden retrievers. Now, the musical has a date, with the show set to debut next August. Dunham is adapting the script with Jessica Huang, while Jepsen is writing the music and lyrics with Ethan Gruska.
10 Things has reached sacred status in the 27 years since it was first released and its novel use of The Taming of the Shrew as inspiration certainly fired up the Shakespeare-to-rom-com pipeline. This has been pretty well-explored territory ever since, right up to 2023’s box-office hit Anyone But You, a loose, modern adaptation of Much Ado About Nothing. It’s no surprise that Shakespeare’s love of mistaken identities, right-place-wrong-time mix-ups, and public declarations lend themselves well to the big screen. As Anyone But You screenwriter Ilana Wolpert told Entertainment Weekly: “They are classic stories, they’re original plots. They are very, very simple, and they work.”
To that end, here are the best rom-coms based on Shakespeare plays to watch—or rewatch—now.
10 Things I Hate About You (1999)
Based on: The Taming of the Shrew
Photo: Getty Images
Kat (Stiles) is an outspoken high school feminist based on Shakespeare’s fiery Katherina Minola. Her lack of appeal to the boys at Padua High School is demonstrated by her love of books, black eyeliner, and combat trousers (yuck!), while her sister Bianca (played by Larisa Oleynik) is the school’s Queen Bee and most coveted romantic prize. Their protective father will only let Bianca date once Kat does, inspiring prospective suitor Cameron (Joseph Gordon-Levitt) to enlist Patrick Verona (Ledger) to seduce Kat so he can take Bianca to a party.
This film gave us so much: Ledger belting out “Can’t Take My Eyes Off You” from the bleachers, Alison Janney’s Ms. Perky secretly writing an erotic novel, and, of course, Kat’s famous poem, which ended: “I hate it when you’re not around, and the fact that you didn’t call. But mostly I hate the way I don’t hate you. Not even close, not even a little bit, not even at all.”
