Julia Stiles (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 (Hamlet and the Othello-inspired O).
She has since had several notable film appearances, including Mona Lisa Smile, The Prince and Me and the Bourne franchise. After graduating from Columbia University, Stiles won an Emmy for her guest role on Dexter. She is currently filming two movies, Hustlers and The God Committee.
Heath Ledger (Patrick Verona)
Ledger went on to receive major critical acclaim 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. He earned a Best Actor Oscar nomination for his turn in Brokeback Mountain, and took the villainous Joker to new depths in The Dark Knight. Ledger died of an accidental overdose before that film’s release in 2008, and was posthumously awarded an Oscar for Best Supporting Actor for his role.
Larisa Oleynik (Bianca Stratford)
Since playing the conceited and popular Bianca (and forever sparking the debate of whether it’s possible to just be “whelmed”), Oleynik has landed roles in a handful of TV shows, including Pretty Little Liars, Mad Men and most recently, Half Life. Oleynik also has an upcoming film, Animal Among Us.
Joseph Gordon-Levitt (Cameron James)
After learning French to woo Bianca in his role as the lovesick Cameron, Gordon-Levitt continued to steal our hearts in several film appearances, most notably the indie smash hit 500 Days of Summer. He also appeared in The Dark Knight Rises and Inception before starring in his 2013 directorial debut, Don Jon. Most recently, Gordon-Levitt portrayed Edward Snowden in Snowden. He currently has several films in post-production.
Andrew Keegan (Joey Donner)
Since playing vain and vapid aspiring model Joey Donner, Keegan has appeared in numerous films and TV series, even reuniting with Stiles for O. He’s best known on the small screen for his role as Wilson West in 7th Heaven. In 2014, he founded the spiritual community center Full Circle Venice, which has since seemingly ceased operations. Keegan currently has a film, Adverse, in post-production.
Gabrielle Union (Chastity)
Union became a Hollywood mainstay after playing Bianca’s social-climbing best friend in 10 Things. After appearing in Bring It On and the Think Like A Man films, Union turned her focus to TV, starring in Being Mary Jane from 2013 to 2019 before taking on her current role of Sydney Burnett in L.A.’s Finest. In 2017, Union became a New York Times best-selling author with her memoir, We’re Going to Need More Wine: Stories That Are Funny, Complicated, and True. She and husband Dwyane Wade welcomed their first child together, daughter Kaavia, via surrogate in 2018.
David Krumholtz (Michael Eckman)
Following his turn as the nerdy and neurotic Michael, Krumholtz continued his role as head elf Bernard in The Santa Clause films, and appeared on a number of TV series throughout the early aughts — most notably, he starred on Numb3rs from 2005 to 2010. He reunited with Allison Janney during his appearances on Mom in 2015, and recently acted on The Deuce. Krumholtz has two films in post-production, and is currently filming On Our Way.
Larry Miller (Walter Stratford)
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. Of his numerous subsequent film and TV appearances, he is perhaps best known for his turn as Princess Mia’s brash stylist Paolo in The Princess Diaries and the sequel. He reprised his role as Mr. Stratford in the short-lived TV reboot of 10 Things, and more recently played Principal Perkales on the mini-series High School Cupid, a Cupid Inc. Story.
Allison Janney (Ms. Perky)
Janney’s role as the high school guidance counselor who is more focused on writing her erotic novel than on her students was one in a long list of more than 130 acting credits to date. On the small screen, the seven-time Emmy Award-winning actress is known for playing C.J. Cregg in The West Wing and Bonnie on Mom. More recently, Janney earned an Academy Award for her turn as Tonya Harding’s mom in I, Tonya. She currently has several movies in pre- and post-production, including the star-studded untitled Roger Ailes project.
Kyle Cease (Bogey Lowenstein)
Cease’s role as the sweater vest-wearing head of the Future MBAs club whose brie-fueled get-together turns into an unintentional rager prefaced his successful career as a comedian and motivational speaker. In 2017, he became a New York Times best-selling author for his book I Hope I Screw This Up: How Falling In Love with Your Fears Can Change the World.
Susan May Pratt (Mandella)
After her turn as Kat’s Shakespeare-obsessed best friend, Pratt appeared in teen movies Drive Me Crazy and Center Stage before landing several roles on the small screen throughout the 2000s, including Masters of Sex and Outcast. Her film Act Super Naturally is currently in post-production.
Daryl Mitchell (Mr. Morgan)
Following his role as Kat, Joey and Patrick’s exasperated English teacher, Mitchell continued to play Leo Michaels on Veronica’s Closet until 2000. After acting and making guest appearances in a number of other TV series, he was on NCIS: New Orleans from 2014 to 2019, as well as Fear the Walking Dead.