10 Things I Hate About You, Then and Now
It’s been two decades since 10 Things I Hate About You, one of the last great rom-coms and teen musts of the 90s, hit theaters and mesmerized the world with Heath Ledger’s ability to serenade a soccer team. Since 1999, the movie, which was inspired by Shakespeare’s The Taming of the Shrew, has been adapted into a TV show — albeit, a shortlived one — and made EW’s list of the 50 Best High School Movies. Check out where the cast is now.
Heath Ledger (Patrick Verona)
Following his turn as longhaired-tough-guy-turned-swoonworthy-“pretty boy” Patrick Verona, Heath Ledger quickly caught the eye of critics. He had acclaimed roles in Brokeback Mountain (2005) — for which he received a Best Actor Oscar nomination — and I’m Not There (2007), playing one of many incarnations of Bob Dylan. Though he did not live to see its release, Ledger starred as Batman’s arch-nemesis, The Joker, in The Dark Knight (2008), the second installment of Christopher Nolan’s trilogy of the same name. Ledger, who died in early 2008, was awarded a posthumous Academy Award for Best Supporting Actor for his role as Gotham’s sociopathic menace.
Julia Stiles (Katarina "Kat" Stratford)
A frequent face in teen flicks of the 90s and early 2000s — she appeared in Mona Lisa Smile (2003), The Prince and Me (2004), and The Omen (2006) remake — Julia Stiles’ most recognizable role in recent years is likely that of Nicky Parsons in the Bourne franchise. She also appeared in Silver Linings Playbook (2012). Since 10 Things, Stiles has graduated from Columbia University, and scored an Emmy nod for her guest role on Dexter. She currently stars as Blue in the web series of the same name.
Larisa Oleynik (Bianca Stratford)
From 1998 until 2000, Larisa Oleynik was appearing on the sitcom 3rd Rock from the Sun alongside 10 Things costar Joseph Gordon-Levitt. Since her role as the spoiled Bianca Stratford, Oleynik has appeared in Mad Men, Pretty Little Liars, and Law and Order: SVU (pictured). She currently has two films in post-production, Animal Among Us, and Accommodations.
Joseph Gordon-Levitt (Cameron James)
Following the conclusion of 3rd Rock, Joseph Gordon-Levitt starred as Jim Hawkins in Disney’s Treasure Planet (2002). A few years later and he would become an indie-darling with 500 Days of Summer (2009). The same year, he appeared in G.I. Joe: The Rise of Cobra, and grew to become a Christopher Nolan favorite, beginning with his role in Inception (2010), and later, The Dark Knight Rises (2012). Gordon-Levitt made his directorial debut with Don Jon in 2013, and most recently, starred as Edward Snowden in the Oliver Stone film, Snowden (2016).
Andrew Keegan (Joey Donner)
Following his role as the aspiring model Joey Donner, Andrew Keegan acted alongside Stiles again, in the 2001 film, O, another adaptation of Shakespeare — this time, Othello. He appeared on 7th Heaven until 2004, and also had a role on the one-season series, Related. Though he’s still acting, Keegan recently founded an organization, known as Full Circle, which Vice has dubbed a “new religion.”
Larry Miller (Walter Stratford)
Larry Miller is no stranger to teen flicks and rom-coms for the ages. The prolific comedy actor is probably best etched in the minds of millennials as snarky stylist, Paolo, in The Princess Diaries (2001) — he broke Mia’s glasses — and the sequel. Among his many, many credits, one highlight is that of his reprisal of the role of Walter Stratford in the 10 Things I Hate About You series. He currently appears on the mini-series High School Cupid, a Cupid Inc. Story.
David Krumholtz (Michael Eckman)
Since playing the ever-neurotic Michael Eckman in 10 Things, David Krumholtz reprised his role as the testy-yet-beloved head elf Bernard in The Santa Clause franchise, and starred on Numb3rs until it ended in 2010. Recently, Krumholtz has appeared in The League, Sausage Party (2016), and his series, The Deuce, will be out this year.
Susan May Pratt (Mandella)
Following 10 Things, Susan May Pratt appeared in Center Stage (2000), and has since had guest roles on Private Practice, Franklin & Bash, and Masters of Sex. Her film Act Super Naturally is currently in post-production.
Gabrielle Union (Chastity)
10 Things wasn’t Gabrielle Union’s only memorable teen hit of 1999; she also appeared in She’s All That. Union’s been busy these past 18 years, appearing in everything from Bring It On, The West Wing, to The Perfect Holiday (2007), to the Think Like a Man films. Union currently stars as Mary Jane Paul on the series, Being Mary Jane.
Allison Janney (Ms. Perky)
In 1999 alone, Janney appeared in multiple series and films including The West Wing, for which she would go on to win four of her seven Emmys, and the Academy Award-winning film, American Beauty. She has since had roles in award-winning films like The Hours (2002), Finding Nemo (2004), and The Help (2011). Janney currently stars in the series Mom alongside Anna Farris, for which she’s won two Emmys, and she has three movies slated for release between now and 2018.
Daryl Mitchell (Mr. Morgan)
Following his role as Mr. Morgan, Daryl Mitchell continued his run on Veronica’s Closet until 2000. He was on Ed from 2002 until 2004, and later had guest appearances on The Suite Life of Zack and Cody, and Desperate Housewives, among others. He’s been on NCIS: New Orleans since 2014.
David Leisure (Mr. Chapin)
To say that the detention scene was… unconventional is an understatement, thanks to David Leisure, whose role as the oblivious Mr. Chapin hit all the right notes. In addition to 10 Things and Fallout, Leisure appeared in a slew of TV shows in 1999, including For Your Love, and Timon & Pumbaa — one of numerous Disney series he’s worked on. After 1999, he also appeared in Behind the Seams, Lloyd in Space, and has frequented soap operas.