The beloved coming-of-age romantic comedy10 Things I Hate About Youis celebrating its 25th anniversary on March 31, 2024. Starring theJulia Stiles, the lateHeath Ledger,Joseph Gordon-LevittandLarisa Oleynik, the film is a modern retelling ofWilliam Shakespeare's comedyThe Taming of the Shrewset in a high school in the late '90s.
Gil Junger's directorial debut follows Gordon-Levitt's Cameron, who develops a crush on Bianca, played by Oleynik. In order to subvert the strict dating rules established by Bianca's father, Cameron makes a deal with the school's bad boy Patrick (Ledger) to date Bianca's older and very antisocial sister Kat (Stiles), leading to manymemorable scenes still quoted today.
In 2021, Gordon-Levitt shared a throwback photoon Instagramfeaturing the core four on the set of the movie. The actor captioned the post: "10 Things I Hate About Youcame out today, March 31st, back in 1999. I'll never forget that summer,making that movie with such wonderful people. The best of times. Still can't believe it was over 20 years ago. <3."
Here's what the cast of10 Things I Hate About Youhas been up to since we last saw them at the fictional Padua High.
Julia Stiles as Kat Stratford
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 Dancecharacter duringa cameo onSaturday Night Livein 2023.
Stiles graduated from Columbia University in 2005 with a B.A. in English literature. In 2017, shemarried Preston J. Cook; the coupleshares two children.
Heath Ledger as Patrick Verona
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 shares with exMichelle Williams.
Larisa Oleynik as Bianca Stratford
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 will celebrate its 30th anniversary in 2025.
Joseph Gordon-Levitt as Cameron James
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 is set to star oppositeEddie Murphyin Netflix's 2024 comedy action sequelBeverly Hills Cop: Axel F.
In 2014, Gordon-Levittmarried girlfriend Tasha McCauley; together,they have two sons.
Andrew Keegan as Joey Donner
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, was born in March 2016.
Gabrielle Union as Chastity
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) andThink 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 andauthored 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, whom Wade is legal guardian.
David Krumholtz as Michael Eckman
Following his turn as the nerdy and neurotic Michael, David Krumholtz continued his role as head elf Bernard in 2002'sThe Santa Clause 2, reprising the part on an episode of the Disney+ seriesThe Santa Clausesin 2022.
He appeared on several TV series throughout the early aughts — most notably,Numb3rsfrom 2005 to 2010.
The actor reunited withAllison Janneyon the CBS sitcomMomin 2015 and appeared on HBO'sThe Deuce. After making hisBroadwaydebut in 1992, Krumholtz returned to the New York stage in Tom Stoppard'sLeopoldstadtfor the 2022–23 season.
In 2023, he was amongthe impressive ensemble castin Nolan's critically acclaimed andOscar-winning historical biopicOppenheimer.
Krumholtz has been married to actress Vanessa Britting since 2010, and the pair havewelcomed two children together.
Larry Miller as Walter Stratford
Larry Miller was already a well-established comedy actor when he landed the role of the hilariously over-protective, 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.
Allison Janney as Ms. Perky
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 on Mom.
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.
Susan May Pratt as Mandella
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, includingMasters 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.
Daryl Mitchell as Mr. Morgan
Following his role as Kat, Joey and Patrick's exasperated English teacher, Daryl Mitchell continued to play Leo Michaels onVeronica's Closetuntil 2000.
In 2001, he was paralyzed from the waist down after a motorcycle crash but 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 three children.
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Tobi Tarwater
Update: 2024-07-05