10 Things I Hate About You

Heath Ledger as Patrick Verona

This was Heath Ledger’s breakthrough American role and he absolutely nailed it. He reportedly improvised the famous bleacher singing scene, adding his own goofy charm to what could have been a cringeworthy moment. Ledger said in interviews that he related to Patrick’s outsider status and brought a lot of genuine warmth to the character underneath the bad boy exterior.

Julia Stiles as Kat Stratford

Julia Stiles was only 17 when filming began and has said Kat is one of her most personal roles. She loved that Kat was unapologetically opinionated and didn’t fit the typical 90s teen movie girl mold. Stiles did a lot of research into feminist literature to really understand where Kat was coming from.

Joseph Gordon-Levitt as Cameron James

This was one of Joseph Gordon-Levitt’s earliest film roles before he became a huge star. He has described Cameron as a genuinely sweet and earnest character which he found refreshing compared to typical teen movie leads. He loved the comedic timing the role required.

Larisa Oleynik as Bianca Stratford

Oleynik was already well known from the TV show The Secret World of Alex Mack. She brought a lot of likability to Bianca, making her more than just a shallow popular girl and giving her real heart throughout the film.