Cast
- Heath Ledger as Patrick Verona, described by a The New York Times reviewer as a "rough-edged outsider" and "teenage rebel" who hangs out at a pool hall, smokes cigarettes, and drinks. He speaks in a partly Australian dialect (often lapsing into American) because he lived in Australia until he was ten. He is based on Petruchio, the male lead of The Taming of the Shrew, and his last name is a reference to his hometown, Verona in the play, coincidentally the setting of Romeo and Juliet.
- Julia Stiles as Katarina "Kat" Stratford, the "shrew" in the film. Kat is a proud, unsociable, nonconforming feminist who listens to Riot Grrrl music and reads books such as The Bell Jar. She is against dating and often "sneers at the idiocy of teenage social life". The New York Times called this "a breath of fresh air in the stifling materialistic atmosphere of today's Hollywood teenage movies". She was accepted into Sarah Lawrence College, which her father initially refused to let her attend. Kat is based on Katherina Minola in The Taming of the Shrew. Her last name is a reference to Shakespeare's home town of Stratford-upon-Avon
- Joseph Gordon-Levitt as Cameron James, who, like Patrick, pursues a Stratford sister. In contrast to Patrick, who is seen as intimidating and manly, Cameron is seen as sweet and delicate. He is a new kid, has a father in the U.S. Army, and befriends Michael and Patrick. He is based on Lucentio from The Taming of the Shrew. The character's name is inspired by film director James Cameron.
- Larisa Oleynik as Bianca Stratford, Kat's younger sister and foil; seen as a "Valley girl" type, she is good looking, wears designer clothes and is popular in school, though she eventually falls for geeky new kid Cameron as opposed to the school's most popular guy, Joey. She is based on Bianca Minola in The Taming of the Shrew.
- David Krumholtz as Michael Eckman, an audiovisual geek who is delegated the task of showing Cameron around. He quickly becomes Cameron's best friend and helps him scheme to win Bianca. He is based on Tranio from The Taming of the Shrew.
- Andrew Keegan as Joey Donner, the main antagonist, a male model, who formerly bedded Kat and makes a bet that he can do the same with Bianca. He is based on Hortensio and Gremio from The Taming of the Shrew.
- Larry Miller as Dr. Walter Stratford, an OB/GYN and single father. He is an extremely overprotective father, believing that his daughters will have sex, do drugs and drink as soon as they aren't under his supervision, though he is incorrect about this for the most part. His character is based on Baptista from The Taming of the Shrew.
- Susan May Pratt as Mandella, a Shakespeare aficionado whom Michael, dressed as William Shakespeare, takes to the prom. She is Kat's best friend.
- Gabrielle Union as Chastity Church, Bianca's selfish and social climbing best friend.
- Daryl Mitchell as Mr. Morgan, the English literature teacher. He's an imposing African-American teacher who, for the most part, seems to keep his classroom under control.
- Allison Janney as Ms. Perky, the school's guidance counselor and a writer of erotic literature. She makes many sexual comments and innuendos throughout the film.
- David Leisure as Mr. Chapin, the detention teacher and the girls' soccer coach.
- Greg Jackson as "Scurvy", one of Patrick's friends.
- Kyle Cease as Bogey Lowenstien, a golf enthusiast (hence his nickname, Bogey) and member of a clique of aspiring MBA's.
- Kay Hanley and Michael Eisenstein, members of Letters to Cleo.
- Monique Powell and Brian Mashburn, members of Save Ferris..
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