’10 Things I Hate About You’ Cast Then and Now: Julia Stiles, Heath Ledger Cult Classic Turns 25
The 10 Things I Hate About You cast probably didn’t know it then, but the actors in the 1999 teen rom-com would get their breakout role. In the 25 years since its release, 10 Things I Hate About You has become a cult classic and a career highlight for its actors.
On the surface, 10 Things I Hate About You doesn’t sound like a recipe for success. A William Shakespeare play reworked into a teen comedy featuring a cast of mostly unknown actors? Critics didn’t fall head over heels for it in 1999, but the movie’s appeal has grown over time and attracted new generations of fans (even if sequel plans failed). And if the 10 Things I Hate About You cast was unknown then, now there is no mistaking the talent of stars like Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt.
Julia Stiles
Julia Stiles led the 10 Things I Hate About You Cast, having previously only played minor supporting roles in films like I Love You, I Love You Not and Wide Awake. She impressed in the role of Kat Stratford, the “shrew” character inspired by Shakespeare’s play. Other names considered for the part included Eliza Dushku, Katie Holmes, and Kate Hudson, who turned down the role.
Stiles, 42, went on to star in a wide range of films, including Save the Last Dance, the Jason Bourne franchise, and Silver Linings Playbook. In 2024, she leads the Prime series The Lake and also stars in the film Chosen Family.
Heath Ledger
Heath Ledger was another unknown when he joined the 10 Things I Hate About You cast as Patrick Verona. Previously, he’d held minor roles in Australian TV and movies. Ledger reportedly beat out Josh Hartnett and Ashton Kutcher for the male lead. His chemistry with Julia Stiles helped him win the part.
Ledger’s profile continued to rise after the 1999 film thanks to roles in The Patriot, Monster’s Ball, and Brokeback Mountain. The actor died in 2008 at the age of 28. Ledger posthumously received an Academy Award for Best Supporting Actor for his role as the Joker in The Dark Knight.
Larisa Oleynik
Larisa Oleynik played opposite Julia Stiles as Bianca, the younger of the Stratford sisters (despite the actors being the same age). She was an established child actor, appearing in a touring production of Les Misérables as well as the Nickelodeon series The Secret World of Alex Mack.
Following 10 Things I Hate About You, Oleynik’s film career never quite took off in the same way. However, she became an in-demand supporting/guest actor on television. Her credits include 3rd Rock From the Sun, Mad Men, and Pretty Little Liars. In 2023, she joined the cast of the Nickelodeon comedy Erin & Andrew.
Joseph Gordon-Levitt
Pining after Bianca in the 10 Things I Hate About You cast was Joseph Gordon-Levitt as Cameron James. Gordon-Levitt had perhaps the best resume among the teenage actors, appearing in A River Runs Through It, Angels in the Outfield, and 3rd Rock From the Sun before joining the rom-com. Gordon-Levitt initially found the role embarrassing but later embraced the film’s popularity.
At 43 years old, Gordon-Levitt remains as busy as ever. His roles in 500 Days of Summer, Looper, and The Dark Knight Rises showcased his versatility. In 2024, he plays Eddie Murphy’s new partner in Beverly Hills Cop: Axel F.
Andrew Keegan
The 10 Things I Hate About You cast had its villain in Andrew Keegan. He played Joey Donner, a stereotypical high school bully with ill intent. Keegan joined the film after building some career momentum in TV series such as Thunder Alley, 7th Heaven, and Party of Five.
Keegan, 45, mainly appeared in direct-to-video and B-movies following 10 Things. On the TV side, he has appeared in guest roles on House and CSI.
David Krumholtz
David Krumholtz played the geeky Michael Eckman, best friend to Cameron. Krumholtz’s career began on Broadway before transitioning to films like Life With Mikey, Addams Family Values, and The Santa Clause.
Krumholtz, now 45, has continued to stand out in TV and movie roles. He reprised his part of Bernard in two Santa Clause sequels and a TV series. Additionally, he held supporting roles in movies like Ray, Superbad, and the Harold & Kumar franchise. In 2023, he appeared in Oppenheimer and the TV series White House Plumbers.
Susan May Pratt
As Mandella, actor Susan May Pratt gave the 10 Things I Hate About You cast a proper nod to its Shakespearean roots. Kat’s best friend was a fan of the Bard while also pursuing Michael. Pratt only had a handful of credits to her name before getting cast in the teen comedy.
Now 50, Pratt does most of her work on television. Guest spots on Mad Men, Masters of Sex, and Outcasts fill out her resume, along with a notable film appearance in The Gift. Pratt will have a starring role in the upcoming thriller Lower Lake.
Gabrielle Union
Gabrielle Union rounded out the 10 Things I Hate About You cast of students. She plays Chastity Church, the friend-turned-enemy of Bianca. It was Union’s second film role after She’s All That and helped launch her career along with Love & Basketball and Bring It On.
The 51-year-old actor has starred in just about every film genre since 10 Things I Hate About You. Her projects in 2024 include the film Riff Raff, co-starring Dustin Hoffman, Jennifer Coolidge, and Brian Cox.
If you’re wondering where to stream 10 Things I Hate About You now, then check out Hulu and Disney+.
