’10 Things I Hate About You’ Cast Then & Now: See Julia Stiles & More After 22 Years

’10 Things I Hate About You’ is a teen rom-com classic. After over 20 years, take a look at the beloved cast then and now.

William Shakespeare was having a moment in the teen rom-com world during the late ’90s. The movie 10 Things I Hate About You put a modern twist on Shakespeare’s The Taming of the Shrew. The film, which was released on March 31, 1999, has since reached top-tier status among millennials.

The movie featured an incredible cast of young actors at the time, but no one stood out more than the swoonworthy Heath Ledger. This film put him on the map and made him one of Hollywood’s most sought-after rising stars. Most of the cast is still working in Hollywood today. Find out where they are now after 22 years:

Julia Stiles

Julia Stiles, 40, starred as Kat Stratford, a.k.a. the “shrew,” in 10 Things I Hate About You. The role was one of her many notable roles in the late ’90s and early ’00s. She went on to star in movies like Save the Last Dance, Down To You, Mona Lisa Smile, The Prince & Me, Silver Linings Playbook, the Bourne film series, and more. Julia had the recurring role of Lumen Pierce in Dexter season 5, which earned her a Golden Globe nomination. Since 2017, she has starred in the series Riviera.

While in college at Columbia University, she dated her 10 Things co-star Joseph Gordon-Levitt. Julia dated David Harbour from 2011 to 2015. She got engaged to Preston J. Cook in 2016. They married in 2017 and have a son together.

Heath Ledger

The role of the dreamy Patrick Verona in 10 Things I Hate About You was Heath Ledger’s breakout role. His roles in the first few years after 10 Things included The Patriot, A Knight’s Tale, Monster’s Ball, Ned Kelly, Lords of Dogtown, and more. Heath received his first Oscar nomination for his performance in the 2005 film Brokeback Mountain.

His most well-known role was The Joker in the 2008 film The Dark Knight. Unfortunately, Heath died on January 22, 2008. He passed away at the age of 28 due to an accidental drug overdose. The Dark Knight was released months later in July. Heath was awarded a posthumous Oscar for Best Supporting Actor in 2009. His final film role was The Imaginarium of Doctor Parnassus.

Heath dated Michelle Williams from 2004 to 2007 after meeting on the set of Brokeback Mountain. Their daughter, Matilda Rose, now 15, was born in 2005.

Larisa Oleynik

Larisa Oleynik, 39, played Bianca Stratford, Kat’s younger sister. Larisa previously rose to fame on The Secret World of Alex Mack and The Baby-Sitters Club. She went on to have roles in movies like 100 Girls, An American Rhapsody, Bringing Rain, and more. She played Cynthia Cosgrove on Mad Men from 2010 to 2015 and had additional recurring roles on Winx Club and Pretty Little Liars. She recently had roles in the Netflix shows Trinkets and The Healing Powers of Dude.

Joseph Gordon-Levitt

Joseph Gordon-Levitt, 40, starred as the lovable Cameron James who is in love with Bianca. After 10 Things I Hate About You, Joseph took a break from acting to attend Columbia University. He dropped out in 2004 to continue acting. His notable roles include Inception, 500 Days of Summer, The Dark Knight Rises, Looper, The Walk, and more. He wrote, directed, and starred in the 2013 movie Don Jon. He recently starred in the Netflix film The Trial of the Chicago 7 and will voice Jiminy Cricket in the upcoming live-action Pinocchio. Joseph married Tasha McCauley in 2014, and they have two children together.

Andrew Keegan

Andrew Keegan, 42, starred as Patrick Donner, the popular and wealthy high school jock who is not-so-nice. In 2001, Andrew reunited with Julia in the 2001 film O, based on Shakespeare’s Othello. He also had the recurring role of Wilson West on 7th Heaven from 1997 to 2002. He has appeared in several shows and movies over the years, with his recent work including the movie Adverse and a guest appearance on the Netflix series Trinkets. Andrew also runs the California spiritual community Full Circle.

Gabrielle Union

Gabrielle Union, 48, played Chastity Church, Bianca’s best friend. The same year as 10 Things I Hate About You, Gabrielle also starred in She’s All That. Her breakout role was in the 2000 film Bring It On. She’s since had roles in movies like Deliver Us From Eva, Bad Boys II, Think Like a Man and its sequel, Top Five, and Breaking In.

One of her most well-known roles was Mary Jane Paul in the BET series Being Mary Jane, which ran from 2013 to 2019. She played Syd Burnett in the series L.A.’s Finest, which ran for two seasons. She was a judge on America’s Got Talent for one season in 2019.

She was married to NFL player Chris Howard from 2001 to 2006. She married NBA star Dwyane Wade in 2014. Their daughter, Kaavia, was born in 2018 via surrogacy.

David Krumholtz

David Krumholtz, 42, played Michael Eckman, Cameron’s best friend. A few years after 10 Things, David reprised the role of Bernard the Head Elf in The Santa Clause sequel. He also starred in the Harold & Kumar trilogy. David notably starred in 6 seasons of NUMB3RS. He’s had recent TV roles on The Deuce, Living Biblically, and The Plot Against America.

David married Vanessa Britting in 2010, and they have two kids together. David was diagnosed with thyroid cancer in 2011. He is now cancer-free.

Susan May Pratt

Susan May Pratt, 47, played Mandella, Kat’s only friend. The same year as 10 Things I Hate About You, Susan starred in the teen flick Drive Me Crazy. She played ballet dancer Maureen Cummings in the 2000 film Center Stage, which has since become a cult classic. Over the years, she’s appeared on Mad Men, Private Practice, Masters of Sex, Outcast, and more. Her latest role was in the 2019 film Act Super Naturally.

Allison Janney

Allison Janney, 61, played the scene-stealing Ms. Perky in 10 Things I Hate About You. The year 1999 was a busy one for Allison. She also starred in the films Drop Dead Gorgeous and American Beauty. On top of those, she began playing C.J. Cregg on The West Wing. The series ran from 1999 to 2006. She won 4 Emmys for her performance.

Allison’s resume includes films like Hairspray, Juno, The Help, The Way, Way Back, Bad Education, Finding Nemo, The Addams Family, and I, Tonya. She won an Oscar for her performance in I, Tonya. The actress began playing Bonnie on the CBS series Mom. She’s won two Emmys for performance on the show, which is now in its eighth and final season. She has a number of films coming up, including Lou, The Heart, and To Leslie.

Larry Miller

Larry Miller, 67, played Walter Stratford, Kat and Bianca’s hilarious father. A few years later, Larry had the scene-stealing role of Paolo in The Princess Diaries. He returned for the sequel. He reunited with Julia in the 2003 film A Guy Thing. He has appeared in countless TV shows and movies, including several more Garry Marshall films. He reprised the role of Walter Stratford in the 10 Things I Hate About You series, a reimagining of the movie. His recent work was in the 2018 movie Second Act.