Cast of 10 Things I Hate About You

Released in 1999, 10 Things I Hate About You is a loose modern adaptation of Shakespeare’s The Taming of the Shrew set in a Seattle-area high school. Directed by Gil Junger, the film features an ensemble cast whose careers ranged from early breakthrough moments to the beginnings of legendary careers. The film is particularly notable in retrospect as one of Heath Ledger’s first American roles.

Heath Ledger — Patrick Verona

Heath Ledger played Patrick Verona, the mysterious, leather-jacket-wearing bad boy who is paid to pursue the sharp-tongued Kat Stratford. The role was Ledger’s breakthrough in American cinema, and his charisma — particularly in the film’s famous stadium bleachers sequence of “Can’t Take My Eyes Off You” — established him immediately as a leading man.

Ledger went on to a remarkable and varied career: A Knight’s Tale (2001), Monster’s Ball (2001), Brokeback Mountain (2005), in which he received an Academy Award nomination for Best Actor, and The Dark Knight (2008), in which his portrayal of the Joker earned him a posthumous Academy Award for Best Supporting Actor. Ledger died in January 2008 at age 28. He remains one of the most talented actors of his generation, and 10 Things I Hate About You preserves a joyful early performance.

Julia Stiles — Kat Stratford

Julia Stiles played Kat Stratford, the feminist, prickly older sister whose academic focus and determined aloofness masks a tender interior. The role required a difficult balance — making Kat’s thorny exterior believable while keeping her sympathetic — and Stiles managed it with intelligence and restraint.

Stiles built a significant career in the years following, including the Bourne film series (2002-2007) alongside Matt Damon, as well as additional Shakespeare adaptations including O (2001) and Save the Last Dance (2001). She has continued working steadily in film, television, and theater.

Joseph Gordon-Levitt — Cameron James

Joseph Gordon-Levitt played Cameron James, the new student at Padua High who falls for Bianca and engineers the scheme to get Patrick to pursue Kat. Gordon-Levitt was 18 during filming and had already built a television resume through 3rd Rock from the Sun (1996-2001).

His subsequent career became one of the most impressive of the film’s ensemble: 500 Days of Summer (2009), Inception (2010), The Dark Knight Rises (2012), Lincoln (2012), Looper (2012), and Don Jon (2013), which he also wrote and directed. He remains one of the busiest and most respected actors of his generation.

Larisa Oleynik — Bianca Stratford

Larisa Oleynik played Bianca Stratford, the popular younger sister whose social ambitions set the film’s plot in motion. Oleynik was already familiar to young audiences as the lead of the Nickelodeon series The Secret World of Alex Mack (1994-1998).

She has continued working in television and film, appearing in Mad Men, Pretty Little Liars, and various independent films. She has been more selective in her career than some of her co-stars but has maintained a consistent presence in the industry.

David Krumholtz — Michael Eckman

David Krumholtz played Michael Eckman, Cameron’s fast-talking, scheming friend who helps engineer the Kat-Patrick matchmaking plan. Krumholtz had already appeared in films including Addams Family Values (1993) and Santa Clause films, and his comedic timing in this role was a highlight.

He is perhaps best known to television audiences for his lead role in the CBS crime drama Numb3rs (2005-2010), in which he played a mathematics professor who assists his FBI brother in solving cases.

Andrew Keegan — Joey Donner

Andrew Keegan played Joey Donner, the shallow, self-obsessed model and object of Bianca’s early affection, who funds Patrick’s courtship of Kat for self-interested reasons. He effectively played the film’s primary antagonist with the right degree of oblivious vanity.

Keegan continued working in television and film through the 2000s, appearing in numerous projects, though he did not achieve the same level of prominent career as some of his co-stars.

Larry Miller — Walter Stratford

Larry Miller played Walter Stratford, the Kat and Bianca’s overprotective, eccentric father whose obsessive fear of his daughters’ sexuality drives significant plot complications. His comedic performance — neurotic, loving, and completely unreasonable — is one of the film’s consistent pleasures.

Miller has had a long career as a character actor and stand-up comedian, appearing in dozens of films and television shows including The Princess Diaries, Pretty Woman, and Boston Legal.

Allison Janney — Ms. Perky

Allison Janney played Ms. Perky, the school guidance counselor who compulsively writes romance novels at her desk during student appointments. It is a small role that Janney made memorable with committed comic excess.

Janney has since become one of the most acclaimed character actresses in American entertainment: Emmy-winning for The West Wing and Mom, and Academy Award-winning for Best Supporting Actress for I, Tonya (2017).

The ensemble of 10 Things I Hate About You is, in retrospect, a remarkable collection of talent caught at various stages of careers that ranged from promising to extraordinary. The film works partly because every role is cast with care — from Ledger’s magnetic lead to Janney’s brief and perfectly calibrated comic appearance. It is a film that rewards watching again with the knowledge of what these careers became.