Maybe you fell head over heels for 10 Things I Hate About You the moment Julia Stiles’ Kat Stratford danced to Biggie on a tabletop and fell into the arms of Heath Ledger’s Patrick Verona, or maybe it was his grand football field serenade. Countless moments in the teen romantic comedy make it special, and one of the most iconic ‘90s movies.
Since its 1999 debut, this contemporary adaptation of William Shakespeare’s The Taming of the Shrew about the dating dilemma of the teenage Stratford sisters (played by Stiles and Larisa Oleynik) has become a rewatchable favorite. It arrived amid a heyday of teen blockbusters, and also—with its memorable soundtrack and thoughtful grip on how challenging it can be to be a young person navigating identity and romance—went on to influence teen movies that followed.
