The Cast of '10 Things I Hate About You,' Then and Now

9:30 AM 3/29/2019

by Jasmyne Bell

The teenage romantic comedy starring Julia Stiles and the late Heath Ledger was released 20 years ago, on March 31, 1999.

This year marks the 20th anniversary for the teenage romantic comedy 10 Things I Hate About You, starring Heath Ledger and Julia Stiles.

In its opening weekend, the film grossed $14.8 million (adjusted for inflation) in 2,271 theaters domestically (according to Box Office Mojo), ranking it at No. 2 at the box office behind The Matrix. It went on to gross $67.9 million domestically (adjusted). Ten years later, a television series spinoff also titled 10 Things I Hate About You aired on ABC Family.

The movie, which is a loose, modernized adaptation of Shakespeare’s The Taming of the Shrew, was a breakout for both Ledger and Stiles when they were just starting out in their acting careers. The cast also included Joseph Gordon-Levitt and Larry Miller. 

In honor of the film's anniversary, The Hollywood Reporter takes a look at what the cast has been up to in the two decades since the rom-com first hit theaters. (Warning: Some spoilers if you haven't seen the movie.)

  • Patrick Verona, played by Heath Ledger

    Photofest; Getty Images

    In his first American film, Ledger scored his breakout role as Patrick Verona, the bad-boy heartthrob who is paid to pursue Kat Stratford (Julia Stiles) in a scheme concocted by a sophomore (Joseph Gordon-Levitt) so that he is able to pursue a date with Kat’s younger sister, Bianca (Larisa Oleynik). When he first rose to fame in 1999, he was labeled as a “pretty boy” actor with little potential for deeper roles. Hollywood was proved wrong when he took on more serious roles in The Patriot; Brokeback Mountain, which earned him an Oscar nom; and The Dark Knight, for which he won a posthumous Oscar for his portrayal of the DC Universe villain The Joker. Ledger died Jan. 22, 2008, due to cardiac arrest following an accidental overdose of prescription medications that included painkillers, anti-anxiety drugs and sleeping pills.

  • Kat Stratford, played by Julia Stiles

    Buena Vista/Photofest; John Phillips/Getty Images

    Stiles played the rebellious, hard-headed Kat Stratford, who was hesitant to accept the affection of Patrick Verona. She eventually ends up falling in love with Patrick after a roller-coaster series of events, with the film ending in her own rendition of a Shakespearean sonnet titled 10 Things I Hate About You. Stiles went on to be in Save the Last Dance, Mona Lisa Smile, The Prince and Me and the Matt Damon Bourne movies.

  • Cameron James, played by Joseph Gordon-Levitt

    Buena Vista Pictures/Photofest; Albert L. Ortega/Getty Images

    Before 10 Things I Hate About You, Joseph Gordon-Levitt had an extensive resume as far as his acting career, including roles in Roseanne and That '70s Show. In the movie, Gordon-Levitt plays Cameron, a newcomer sophomore who has eyes for Kat’s younger sister, Bianca (Oleynik). When he discovers that Bianca’s father refuses to let her date before her older sister, Kat, Cameron pays Patrick (Ledger) to ask Kat on a date. Gordon-Levitt went on to play more memorable roles in films such as (500) Days of Summer, Inception and The Dark Knight Rises.

  • Bianca Stratford, played by Larisa Oleynik

    Buena Vista Pictures/Photofest; Getty Images

    Oleynik landed her role as Bianca Stratford after she was in The Babysitter’s Club and played a minor role in Boy Meets World. Bianca is the temperamental younger sister of Kat who just wants the chance to date senior Joey Donner, who previously dated Kat. As the story progresses, she inevitably realizes that Joey is just another sleazy teenage guy and eventually falls for Cameron (Gordon-Levitt). Oleynik continued her acting career and later starred in another production with Gordon-Levitt, the TV series 3rd Rock From the Sun. More recently, she recurred on Mad Men and made a guest appearance on Law & Order: Special Victims Unit.

  • Joey Donner, played by Andrew Keegan

    Buena Vista Pictures/Photofest; David Livingston/Getty Images

    In 10 Things I Hate About You, Keegan plays the malicious Joey Donner. When he loses his romantic grip on Bianca, he reveals to Kat the schemes of Cameron and Patrick. Before portraying Donner, he appeared in popular '90s shows Full House, Sabrina the Teenage Witch and Boy Meets World and had recurring roles in the television series Party of Five and 7th Heaven. His more recent credits include mostly guest appearances on various TV series.

  • Chastity Church, played by Gabrielle Union

    Courtesy of Photofest; Roy Rochlin/Getty Images

    Gabrielle Union played Chastity in 10 Things I Hate About You in 1999, the year that marked her big-screen debut with not only this film but another teen rom-com, She's All That (released Jan. 29, 1999). Previously, she had a recurring role in the TV series Sister, Sister. Union went on to appear in other '90s movies and television shows, including 7th Heaven, and then went on to play Isis in the iconic cheerleading movie Bring It On, released in 2000. Union recently starred in the thriller Breaking In, where she portrayed a woman who must find a way to protect her family during a home invasion.

  • Walter Stratford, played by Larry Miller

    Getty Images (left)

    Comedian Larry Miller played Mr. Stratford, an obstetrician who just wants to protect his daughters from teenage boys. At first putting a restriction on their dating life until they graduate, he proposes the idea that Bianca (Oleynik) can date when Kat (Stiles) gets asked on one, knowing that this is unlikely due to Kat’s antisocial personality. Earlier in his career, he took on roles in The Princess Diaries, Max Keeble’s Big Move and My Wife and Kids. More recently, he appeared in the Jennifer Lopez movie Second Act and guest-starred on NCIS.