It's been 20 years since we were graced with one of the most epic teen movies of all time, 10 Things I Hate About You. The film premiered on March 31, 1999, and with it turned Julia Stiles, Larisa Oleynik and the late Heath Ledger into household names. Adapted from Shakespeare's The Taming of the Shrew, the movie starred Stiles as Kat Stratford, an abrasive teen just trying to get through high school, and her younger sister, Bianca, a popular sophomore who can't go on a date unless her sibling does. Cue hilarity and the most memorable cover of "Can't Take My Eyes Off You" ever. Go ahead and break out your Letters to Cleo albums and ringer tees -- we've got some memories to relive here, people!
Julia Stiles: Then
Stiles starred in the teen drama as Kat Stratford, an abrasive, anti-social teen who just wants to get through high school, make sure her sister doesn't hook up with Joey Donner, and dammit, get into Sarah Lawrence! But just like us, she didn't hate Patrick Verona, not even a little bit, not even at all.
Julia Stiles: Now
Shakespeare was pretty much the name of Stiles' game in the '00s, as she also appeared in the adaptations of Hamlet and O (for Othello), but she also strapped into ballet shoes for 2001's Save the Last Dance. A Columbia University grad, she remained a familiar face in movies, starring in Mona Lisa Smile, Down to You, The Omen and the Bourne franchise, and also won an Emmy for a small screen role after guest starring on Dexter in 2010. Though it's felt like she's taken a bit of a break, she has appeared in smaller roles on TV and in film, and she's poised to make a big comeback in Hustlers and The God Committee.
Larisa Oleynik: Then
'90s kids were very aware of Oleynik ahead of 10 Things I Hate About You's debut, as she starred on the Nickelodeon show, The Secret World of Alex Mack. The 1999 flick was a very different role, as she played Bianca, as popular as her sister was loathed. We hope that after graduation, she did go to Europe to find out if one can just be whelmed.
Larisa Oleynik: Now
After her teen idol days, Oleynik attended Sarah Lawrence College, which we think Kat would have been very proud of. In the years since, she's mostly had guest-starring roles, which included stints on Mad Men, Pretty Little Liars, Hawaii Five-O and Law & Order: Special Victims Unit. Last year, she appeared on the TV show Half Life and her latest film, Auggie, was released in March.
Heath Ledger: Then
We gladly let Ledger run over our hearts as bad boy Patrick Verona, who honestly wasn't that bad but did drive an awesome car, hated peas, and still makes us swoon any time we here "Can't Take My Eyes Off You."
Heath Ledger: Now
Tragically, Ledger died of an accidental overdose in January 2008. He left behind one daughter, Matilda, with his ex-girlfriend, Michelle Williams. He died during the editing of The Dark Knight, in which he played The Joker, and while filming The Imaginarium of Doctor Parnassus. Ledger won many posthumous awards for his unforgettable role in The Dark Knight, including the Academy Award for Best Supporting Actor.
Joseph Gordon-Levitt: Then
Like Oleynik, Gordon-Levitt was also a child star, having starred in 1994's Angels in the Outfield as well as quite a few guest roles on shows like Roseanne, That '70s Show and Dr. Quinn, Medicine Woman. He was starring on the sitcom 3rd Rock From the Sun when he was cast as nerdy Cameron James, who desperately wanted to date Bianca, in 10 Things I Hate About You.
Joseph Gordon-Levitt: Now
Gordon-Levitt has had quite the Hollywood career! Not only was he an indie dream, especially starring alongside Zooey Deschanel in 2009's 500 Days of Summer, he also made a splash in 50/50, The Dark Knight Rises and Don Jon. He started his own production company, HitRECord, which helps up-and-coming artists make a splash in various entertainment projects, and has been a producer, director, writer (including Don Jon!) and editor.
Andrew Keegan: Then
Keegan was already a Tiger Beat heartthrob when he was cast as the arrogant, wealthy aspiring model who wants nothing but to sleep with Bianca. There was nary a hit '90s show that the actor didn't appear on, including Boy Meets World, Moesha, Step by Step, Baywatch and Full House, but his biggest pre-10 Things role was as Reed Isley on Party of Five.
Andrew Keegan: Now
These days, Keegan is as well known for 10 Things as he is for playing Wilson West on 7th Heaven. He's had mostly bit roles since, with his last major role coming in 2018's Living Among Us, and he has a film called Adverse in post-production. In recent years, he's been most associated with co-founding Full Circle Venice, an open source spiritual community center in the Los Angeles area.
Gabrielle Union: Then
We have Bianca's ditzy BFF, Chastity (Union) to thank for giving us the beauty that is contemplating if you can be just whelmed, but we also know she was kind of the worst for betraying Bianca and going out with Joey. As if! (Wait, wrong teen movie.)
Gabrielle Union: Now
Let's be honest, Union needs no re-introduction. Though 10 Things was her first movie, she went on to star in Bring It On, Love & Basketball, Bad Boys II and the Think Like a Man films. She's since been more prominent in television, having starred on Being Mary Jane for its entire run, is one of the newest additions to the judges table on America's Got Talent, and will soon be seen in the upcoming L.A.'s Finest, co-starring Jessica Alba in a spin-off from her Bad Boys II role. She's also a mainstay at her hubby, Dwyane Wade's basketball games (well, before he retires this year), and the pair recently welcomed their first child together via surrogate.
David Krumholtz: Then
Krumholtz played the geeky, anxious Michael Eckman, who ends up becoming Cameron's best friend in order to help him win over Bianca -- mainly so he can woo Kat's pal, Mandella. He's the main reason the scheme to get Kat and Patrick to date gets off the ground at all.
David Krumholtz: Now
The New York native has had no shortage of roles after 10 Things. He delighted moviegoers as the equally neurotic elf, Bernard, in The Santa Clause franchise, plus he's starred on a number of TV shows, including Numb3rs, The Good Wife and The Deuce. He's still good friends with Gordon-Levitt and was reunited with their 10 Things co-star, Allison Janney, on Mom.
Allison Janney: Then
Janney made quite the memorable turn as Padua High School's guidance counselor, Ms. Perky, who was much more interested in getting her erotic novel completed than giving useful advice to her students. To end, that cat mug!
Allison Janney: Now
The acclaimed actress is arguably the biggest Hollywood mainstay of the cast, and she has the awards to prove it. Janney won four Emmys for her turn as presidential press secretary C.J. Cregg on the award-winning D.C. drama, The West Wing, two for her current role as Bonnie on the CBS sitcom, Mom, and one for Outstanding Guest Actress for a recurring role on Masters of Sex, plus she won an Academy Award for her turn as Tonya Harding's mom in the film, I, Tonya. On the big screen, she's also appeared in Hairspray, The Help and The Girl on the Train, and despite all that, she's still a mainstay in theatrical productions. In 2016, she received a star on the Hollywood Walk of Fame. She's also just delightful.
Larry Miller: Then
Some of the best lines in 10 Things came from Miller's Walter Stratford, the overprotective, single father of Kat and Bianca. The obstetrician tries his hardest to convince his kids to never date or have sex, at one point even making Bianca wear "the belly," much to her BFF's disgust. He was well-established before the teen drama came along, with parts on Dream On, Life's Work and Mad About You, and film credits that included The Nutty Professor, Waiting for Guffman and L.A. Story. He was even on an episode of Gordon-Levitt's 3rd Rock From the Sun.
Larry Miller: Now
Miller was no less prolific after starring alongside Stiles and Oleynik. He appeared in the Nutty Professor sequel and gained a whole new set of teen movie fans as Paolo in The Princess Diaries franchise, and he popped up on quite a few sitcoms. A decade after first portraying Walter, he reprised the role for the short-lived TV show of the same name. Miller was last seen in the Jennifer Lopez vehicle, Second Act.
Susan May Pratt: Then
Let us count the ways Pratt's Mandella -- Kat's only real friend -- was obsessed with Shakespeare. Luckily, she had Michael by her side at prom to fulfill her Brit lit fantasies.
Susan May Pratt: Now
10 Things was her first major movie role, but Pratt quickly became a familiar face in teen dramas, playing pals of the protagonists in Drive Me Crazy and Center Stage. She was so recognized for those roles that it's easy to forget that after 2000, she had mostly guest spots on various shows, including Charmed, Private Practice, Franklin & Bash and Masters of Sex. She had spurts of acting gigs in 2012, 2015 and 2017, but was last seen in the 2008 short, The Girl on the Roof, and has one film, Act Super Naturally, in post-production.
Kyle Cease: Then
Poor Bogey Lowenstein. Michael's wealthy nemesis loved golf and leading the Future MBAs, so it's easy to say that he never expected to throw the house party of the year (or, at least, save his parents' vases from breaking during it).
Kyle Cease: Now
10 Things was Cease's first film and most prominent role. Though he would go on to appear in Not Another Teen Movie and had a couple of small roles on shows and in shorts, he focused on his first love, stand-up comedy, before moving into motivational speaking. He's also a published author, releasing I Hope I Screw This Up: How Falling in Love With Your Fears Can Change the World in 2017 and his follow-up, The Illusion of Money: Why Chasing Money Is Stopping You From Receiving It, will hit shelves later this fall.
Daryl Mitchell: Then
English teacher Mr. Morgan often seemed like the only adult in the room, namely because he wouldn't take crap from anyone and could rap Shakespeare.
Daryl Mitchell: Now
Mitchell was paralyzed from the waist down after a motorcycle accident in 2001, but that hasn't stopped him from continuing to act. Though confined to a wheelchair, the actor and disability advocate appeared on Ed as a bowling alley manager who had been in a similar accident, starred on NCIS: New Orleans as Patton Plame from 2014-2019, and acted on Fear the Walking Dead. The father of three started the Daryl Mitchell Foundation to raise awareness for spinal cord industries and is a spokesperson for the Christopher Reeve Foundation.