Richard Cartwright/Touchstone Pictures Julia Stiles and the late Heath Ledger starred in the 1999 hit rom-com10 Things I Hate About You The coming-of-age film also featured Joseph Gordon-Levitt, Larisa Oleynik, Andrew Keegan and Gabrielle Union, among others More than two decades after the movie's premiere, several of the stars have gone on to win various awards for other acting roles 10 Things I Hate About Youhas captured the hearts of teens everywhere ever since it premiered in 1999. The hit romantic comedy, which is a modern retelling of the William Shakespeare playThe Taming of the Shrew,starredJulia Stiles, the lateHeath Ledger,Joseph Gordon-LevittandLarisa Oleynik. In the film, Gordon-Levitt's character convinces Ledger's bad boy character to date Stiles' character, so he can, in turn, date her sister. The hit teen rom-com also inspired aTV series of the same nameand anupcoming Broadway musicalfromLena DunhamandCarly Rae Jepsen. After more than two decades,Gil Junger, who directed the original film, exclusively revealed to PEOPLE that he's working on afollow-up film, called10 Things I Hate About Dating. In addition to the first follow-up film, Junger teased that he hopes to make it a trilogy, followed by10 Things I Hate About Marriageand10 Things I Hate About Kids. The success of10 Things I Hate About Youskyrocketed many of the stars' careers, leading many of them to other prominent roles in TV shows and movies. Ledger, who will forever count the rom-com as part of his legacy, tragicallydied in 2008 at age 28. Here's everything to know about where the cast of10 Things I Hate About Youis now. 01 of 12 After playing the snarky, anti-mainstream, feminist lead who learns to loosen up (who could forget that iconic table dancing scene?) and let love in, Stiles went on to star in two other film adaptations of Shakespeare plays in the early aughts (2000'sHamletand 2001'sOthello-inspiredO). She made notable appearances in other films, includingSave the Last Dance(2001),Mona Lisa Smile(2003),The Prince and Me(2004),Hustlers(2022),Orphan: First Kill(2022),Chosen Family(2024) and theBournemovie franchise. In 2011, Stiles was nominated for anEmmyfor her guest role onDexter. The actress later reprised herSave the Last Dancerole duringa cameo onSaturday Night Livein 2023. Stiles graduated from Columbia University in 2005 with a bachelor's degree in English literature. In 2017, shemarried Preston J. Cook; the couple sharethree children. 02 of 12 After serenading the soccer team in one of the most swoon-worthy scenes of all time while playing the mysterious, charming and seemingly rough-around-the-edges Patrick, Ledger went on to receive major critical acclaim. He earned a Best ActorOscar nominationfor his turn in 2005'sBrokeback Mountainand took the villainous Joker to new depths in 2008'sThe Dark Knight. However, Ledger tragicallydied of an accidental overdosebefore the film's release. He wasposthumously awardedan Oscar for Best Supporting Actor for his role, with Ledger's parents and sister accepting the award on his behalf. The star's father, Kim, said, "Firstly, we would like to thank the Academy for recognizing our son's amazing work. This award tonight would have humbly validated Heath's quiet determination to be truly accepted by you all here, his peers within an industry he so loved." Ledger's other notable roles include the Oscar-nominatedThe Patriot(2000),A Knight's Tale(2001)and the Academy Award-winning dramaMonster's Ball(2001), along withThe Four Feathers(2002),Ned Kelly(2003),The Order(2003),Lords of Dogtown(2005) andThe Brothers Grimm(2005). He is survived bydaughter Matilda, whom he shared with exMichelle Williams. 03 of 12 Since playing the conceited and popular Bianca (and forever sparking the debate of whether it's possible to just be "whelmed"), Oleynik landed roles on a handful of TV shows, includingPretty Little Liars,Mad MenandHalf Life. The actress reunited with Gordon-Levitt when she played the girlfriend of his alien character Tommy Solomon on the Emmy Award-winning show3rd Rock from the Sun. Oleynik later appeared onTrinketsandThe Healing Powers of Dude, the Daytime Emmy-winning comedy series costarringTom Everett Scott. The former child star is also known for starring as Dawn Schafer in 1995'sThe Baby-Sitter's Club, which celebrated its 30th anniversary in 2025. 04 of 12 After learning French to woo Bianca as the lovesick Cameron, Gordon-Levitt continued to steal our hearts in other film appearances, most notably the 2009 indie hit(500) Days of Summer. He also appeared inChristopher Nolan'sInception(2010) andThe Dark Knight Rises(2012) before starring in his own 2013 directorial debut,Don Jon. Gordon-Levitt appeared in the filmThe Trial of the Chicago 7(2020) and on the Apple TV seriesMr. Cormanand Showtime'sSuper Pumped: The Battle for Uber. The Emmy-winning actor went on to star oppositeEddie Murphyin Netflix's 2024 comedy action sequelBeverly Hills Cop: Axel F. In 2014, Gordon-Levitt married Tasha McCauley; together, they havethree children. 05 of 12 Since playing vain and vapid aspiring model Joey Donner, Keegan has appeared in numerous films and TV series, even reuniting with Stiles forO. He's best known on the small screen for his role as Wilson West on7th Heaven. In 2014, Keegan founded thespiritual community center Full Circle Venice, which has since seemingly ceased operations. The actor starred alongside horror alums Tony Todd and Kane Hodder in the 2023 thrillerThe Activated Man. The movie won several awards at various film festivals. Keegan's daughter,Aiya Rose, whom he shares with Arista Ilona, was born in March 2016. 06 of 12 Gabrielle Unionbecame a Hollywood mainstay after playing Bianca's social-climbing best friend in10 Things I Hate About You. In addition to her appearances inBring It On(2000) and theThink Like A Manfilm series, Union turned her focus to TV, starring on BET'sBeing Mary Janebefore reprising herBad Boys IIrole of Sydney Burnett onL.A.'s Finest. In 2017, Union became aNew York Timesbest-selling author with her memoirWe're Going to Need More Wine: Stories That Are Funny, Complicated, and True.She released her second memoir,You Got Anything Stronger?,in 2021 and hasauthored two children's books. In 2023, she starred on the Apple TV+ crime seriesTruth Be ToldalongsideOctavia Spencer. Union and former NBA playerDwyane Wadetied the knotin 2014; the couplewelcomed their first child together, daughterKaavia, via surrogate in 2018.She is also stepmotherto Wade's three children from two previous relationships, as well as Wade's nephew Dahveon Morris, for whom Wade is legal guardian. 07 of 12 Following his turn as the nerdy and neurotic Michael,David Krumholtzcontinued his role as head elf Bernard in 2002'sThe Santa Clause 2, and reprised the part on an episode of the Disney+ seriesThe Santa Clausesin 2022. He appeared on several TV series throughout the early aughts — most notablyNumb3rsfrom 2005 to 2010. The actor reunited withAllison Janneyon the CBS sitcomMomin 2015 and appeared on HBO'sThe Deuce. After making his Broadway debut in 1992, Krumholtz returned to the New York stage in Tom Stoppard'sLeopoldstadtfor the 2022–23 season. In 2023, he was part ofthe impressive ensemble castin Nolan's critically acclaimed andOscar-winning historical biopicOppenheimer. Krumholtz has been married to actressVanessa Brittingsince 2010, and the pair havewelcomed two children together. 08 of 12 Touchstone Pictures; John Shearer/WireImage Larry Miller was already a well-established comedic actor when he landed the role of the hilariously overprotective, teen pregnancy-fearing father of Kat and Bianca. Among his numerous subsequent film and TV appearances, he is perhaps best known for his turn as Princess Mia's brash stylist Paolo inThe Princess Diariesand its sequel, along withPretty Woman(1990) andA Mighty Wind(2003). Miller reprised his role as Mr. Stratford in the short-lived TV reboot of10 Things I Hate About Youand also played Principal Perkales on the miniseriesHigh School Cupid, a Cupid Inc. Story. He has been married to producer Eileen Conn since 1993, and the couple share two children. 09 of 12 Janney's role as the high school guidance counselor who is more focused on writing her erotic novel than on her students is one in a long list of acting credits. On the small screen, the Emmy Award-winning actress is known for playing C.J. Cregg onThe West Wingand Bonnie onMom. In 2018, Janney earned an Academy Award for her turn as Tonya Harding's mom inI, Tonya. She followed that up with appearances in the critically acclaimed filmsBombshell(2019) andTo Leslie(2022). She then starred oppositeJohn David WashingtonandGemma Chanin the 2024 Oscar-nominated action dramaThe Creator. 10 of 12 Kyle Cease's role as the sweater vest-wearing head of the Future MBAs club, whose brie-fueled get-together turns into an unintentional rager, followed his successful career as a comedian as a motivational speaker. In 2017, he became aNew York Timesbest-selling author for his bookI Hope I Screw This Up: How Falling In Love with Your Fears Can Change the World.He followed it up with the 2019 release ofThe Illusion of Money: Why Chasing Money Is Stopping You from Receiving It. 11 of 12 After her turn as Kat's Shakespeare-obsessed best friend, Pratt appeared in teen moviesDrive Me Crazy(1999) andCenter Stage(2000) before landing several roles on the small screen throughout the 2000s, including inMasters of SexandOutcast. She has two children with her actor husband,Kenneth Mitchell, whodied at the age of 49on Feb. 24, 2024, five years after beingdiagnosed with ALS. 12 of 12 Following his role as Kat, Joey and Patrick's exasperated English teacher, Daryl Mitchell went on to play Leo Michaels onVeronica's Closetuntil 2000. In 2001, he was paralyzed from the waist down after a motorcycle crash, but he has continued acting and making guest appearances on a number of other TV series, most notablyEd. He was onNCIS: New Orleansfrom 2014 to 2019, as well asThe Walking Deadspin-offFear the Walking Dead. He is married with four children. Read the original article onPeople
