18 Movies to Watch If You Love “10 Things I Hate About You”

“10 Things I Hate About You” — the 1999 modern retelling of Shakespeare’s controversial comedy “The Taming of the Shrew” — remains a high school comedy classic more than two decades after its release. In the rom-com, new student Cameron (Joseph Gordon-Levitt) wants to go out with popular sophomore Bianca (Larisa Oleynik). There’s just one problem: not only is Bianca more interested in senior Joey (Andrew Keegan), she also can’t date unless her older sister, Kat (Julia Stiles), dates, their overprotective father’s rule. This leads Cameron to come up with a plan: he persuades bad boy Patrick (Heath Ledger) to woo Kat — for a price, of course. And Patrick has certainly got his work cut out for him since Kat — a feminist who’s been burned by boys before — is very much anti-dating. Eventually, Patrick wins her over and starts to (gasp!) catch real feelings for her.

The movie is packed with unforgettable moments, like when Kat drunkenly dances on top of a table, and when Patrick serenades Kat on the school’s bleachers as a romantic grand gesture. Who didn’t want to go out on a paintball date after that scene of Patrick and Kat making out covered in paint? Oh, and not to mention that iconic punch Bianca lands on Joey.

The film is full of young actors who went on to become stars, including Gabrielle Union, who was criminally underused in quite a few ’90s and early-2000s teen movies. And Allison Janney has an iconic turn as a school guidance counselor who writes erotic fiction in her spare moments. “10 Things I Hate About You” has definitely stood the test of time with its strong, feminist woman lead, but it’s definitely a product of its time when the landscape of teen rom-coms was overly white and heteronormative.

If you want another movie that makes you feel all the giddiness of “10 Things,” we’ve got you covered. From other movies that adapt classic works to teen comedies with a feminist bent to other favorite films featuring the movie’s stars, here are 18 movies like “10 Things I Hate About You.”