
1999 · Gil Junger
How 10 Things I Hate About You has been received, argued over, and remembered.
A solid-but-unspectacular hit in 1999, filed alongside the era's other teen Shakespeare updates — it has since climbed to consensus status as maybe the best teen movie of its generation, a comfort-watch canon fixture rather than a nostalgia curio.
Fans regularly argue over whether it's the peak of the 90s teen-movie boom (over Clueless, over She's All That) — and whether Kat Stratford reads as a genuinely ahead-of-its-time heroine or a defanged one.
Heath Ledger serenading 'Can't Take My Eyes Off You' from the bleachers is one of the most referenced and parodied romantic gestures in modern movies, and 'I know you can be overwhelmed, and you can be underwhelmed, but can you ever just be whelmed?' still circulates as a quote.
A Letterboxd perennial — the rare studio teen comedy that gets 'you must have seen this' treatment from cinephiles who'd shrug at its 1999 classmates.