There are certain films that define a generation, and for any teen growing up in the late 1990s and early 2000s, 10 Things I Hate About You was definitely a movie that was most likely seen on repeat.
Based on Shakespeare's Taming of the Shrew, 10 Things I Hate About You brings the Bard's love story into the 20th Century, with paintballing, ska music, and some very '90s fashion to boot.
Starring the late, great Heath Ledger and Julia Stiles as the two main love interests, 10 Things I Hate About You is seen today as a nostalgic look back on an actor whose career was cut too short to quickly, and a host of familiar faces that were only just getting their start in acting.
Seeing the difference between what these actors looked like in this 1999 film versus how they are now is staggering, as many have gone on to do bigger and greater things, while others who were in their prime in the late 90s seem to have now all but disappeared.
Get ready to hop on board the nostalgia train as we go back in time to a simpler, more plaid-filled time, as we take a look at what these '90s heartthrobs and icons are up to today.
Here's 10 Things I Hate About You: What The Cast Looked Like In The Movie Vs Today
15 Larisa Oleynik (Bianca Stratford)
Larisa Oleynik is another star who rose to fame in the early 1990s, making her big TV appearance in Nickelodeon’s The Secret World of Alex Mack from 1994 to 1998, then in Boy Meets World between 1996 and 1998, before going on to 3rd Rock From The Sun in 1998 to 2000 in which she starred alongside 10 Things I Hate About You love interest Joseph Gordon-Levitt.
Larisa Oleynik absolutely nailed her role as spoiled Bianca Stratford in 10 Things, and for many people, this is certainly the role they will continue to most associate with her. With her squeaky-clean image and bubbly persona, Oleynik was the perfect fit to play the high school sweetheart JGL’s character chased after.
Since her signature role in 10 Things I Hate About You, Larisa Oleynik has continued to find success, mainly in TV roles.
She has starred in Mad Men as Cynthia, Pretty Little Liars as Maggie Cutler, and Hawaii Five-0 as Jenna Kaye, among many other projects. She also has two feature films in the works, and people are wondering whether or not there will be a reboot happening anytime soon of The Secret World of Alex Mack. If there were going to be one, would it star Oleynik? We’ll just have to wait and see.
14 Joseph Gordon-Levitt (Cameron James)
It really is heartwarming to see pictures of Joseph Gordon-Levitt as a teen actor compared with how he looks now, as the transformation is pretty staggering. Although there are definitely traces of the lanky, slightly awkward boy we all came to know from 3rd Rock From the Sun and 10 Things I Hate About You, it’s safe to say that Joseph Gordon-Levitt hasn’t only grown up, he’s glowed-up too.
Since his days on the set of 10 Things I Hate About You, JGL has gone on to do numerous roles in both television and film. He has starred and appeared in some of the biggest blockbuster movies to be released in recent years, including 500 Days of Summer, Inception, 50/50, The Dark Knight Rises, Looper, Lincoln, and Snowden among countless others.
Joseph Gordon Levitt, although adorable in his teen years, has proven to the world that he is a credible, talented actor whose versatility allows him to shine whether he’s playing an indie rom-com love interest, or a key part in a thriller filled with action.
Most recently, JGL voiced Slowen Lo in Star Wars: The Last Jedi, and with multiple projects he’s involved with having been announced and in post-production, it seems that this actor’s workload has yet to slow down.
13 Julia Stiles (Katerina “Kat” Stratford)
Julia Stiles was very much a darling of the 1990s and 2000s, and she appeared in many cult teen-classics like Save the Last Dance, Down to You, and The Prince and Me, among many others.
Despite being in a whole host of different projects including film and TV, one of Stiles’ most recognizable roles in recent years was her part in The Bourne films, in which she plays Nicky. In terms of the amount of work the actress has taken on over the years, her projects have overall seemed strong and have not seemed to wane, although it’s safe to say that she is not really on our radars as much these days.
Perhaps Stiles peaked in her days as a 90s and 2000s rom-com queen, but if you look closely enough, you’re still likely to find her popping up on your screen, especially if you’re tuning into British TV series Riviera.
This most recent project has garnered Stiles a lot more attention of late, although the reviews of the show haven’t exactly been stellar. If anything, Stiles has proven that she can tackle any genre of TV and film, from rom-coms to action thrillers, so we’re certain there will be more in store for this actress in the near-future.
12 Andrew Keegan (Joey Donner)
Although Andrew Keegan was a familiar face as a teen actor in the 1990s and early 2000s, starring in shows such as Party of Five and 7th Heaven, he is undoubtedly best remembered as the self-centered, wannabe model Joey Donner in 10 Things I Hate About You. With his handsome looks, and lothario swagger, Keegan was an instant match for Donner’s character, making him the bad boy we all kind of loved despite his very obvious shortcomings.
Since 10 Things, Keegan has done a lot of TV work and short movies, but it’s clear that since his teen hunk days, his roles have slowed down quite a bit.
He's definitely not on most people’s cultural radars anymore.
Although he might not be doing as much screen-work as he used to, Keegan has been keeping himself busy in other ways. Several years ago, Keegan began his own spiritual movement and “church” called Full Circle, based in Venice, California.
Keegan has also spoken out in support of bringing back 10 Things I Hate About You in some kind of capacity, telling US Weekly: “I was thinking they should do some kind of remake or revisit to that project. Maybe that would happen. I think it would be really cool. This seems to be happening a lot. There is a lot of nostalgia around those kinds of projects. So I’m just putting it out there.”
11 Susan May Pratt (Mandella)
Although she might have just had a secondary part in 10 Things I Hate About You, Susan May Pratt’s character Mandella certainly made an impact on anyone who watched the movie. With her bohemian style and love of Shakespeare, Mandella was a calm, artsy counterpart to her best friend Kat’s more temperamental character.
10 Things I Hate About You was one of Pratt’s first big roles, having only appeared in bit parts in a few other projects, including one episode of Law & Order. Following her role in 10 Things, Susan May Pratt was in a couple of beloved teen classics: Drive Me Crazy and Center Stage in 1999 and 2000 respectively.
Since the late 1990s and early 2000s though, Pratt’s roles have failed to be anything but side parts.
She did appear in Charmed, Private Practice, Mad Men, and CSI, but most of these TV roles were as minor characters and just guest appearances, failing to land any significant, recurring parts.
Instead of focusing on the lack of success her acting career brought her, Susan May Pratt decided instead to turn her attentions back on books. According to a feature on Pratt in Buzzfeed, the actress went back to school in order to finish her Bachelor’s degree in business. Clearly a plan B is never a bad thing.
10 David Krumholtz (Michael Eckman)
David Krumholtz was Joseph Gordon-Levitt’s right-hand man in 10 Things I Hate About You, playing the neurotic, hopelessly unpopular character Michael Eckman. Before earning a role in 10 Things, Krumholtz’s most notable role was playing Bernard in The Santa Clause which, even though we can all agree is a childhood classic, isn’t exactly an award-winning part.
Despite being in a handful of well-known movies since 10 Things I Hate About You, including Harold and Kumar Go to White Castle, Superbad, and Sausage Party, Krumholtz’s career has mainly been successful in the area of television work.
It seems that his aptitude for playing a great geek came in handy, as he landed himself a key part in Numb3rs, which ran from 2005 to 2010.
One of David Krumholtz’s most recent roles was in Woody Allen’s 2017 film Wonder Wheel, which the actor has stated he regrets doing. Flying the flag for the #MeToo movement, Krumholtz took to Twitter in January this year to state: “I deeply regret working with Woody Allen on Wonder Wheel. It’s one of my most heartbreaking mistakes.”
For some this statement might be counted as too little, too late, but Krumholtz is one amongst many actors who have spoken out against Allen over the allegations made against him by daughter Dylan Farrow.
9 Gabrielle Union (Chastity)
Although most rom-com aficionados will probably most associate Gabrielle Union with her unforgettable role as Isis in the cheertastic film Bring It On, it should never be forgotten that she also featured in none other than 10 Things I Hate About You. Playing the part of Chastity, Bianca’s Stratford’s supposed best friend in the film, Gabrielle Union delivered a distinct unlikability to the role, which was required of her character.
Union had already starred in a number of big projects before being cast as Chastity in 10 Things I Hate About You, including Moesha, Sister, Sister, She’s All That, and 7th Heaven. Post-10 Things, Union continued to enjoy success in films and TV shows such as Clueless and ER and the movie Love & Basketball, but it was definitely her starring role in Bring It On that really shot her to fame.
Since then, Union has continued to be in the spotlight and gained roles in films such as Bad Boys II, Running with Scissors, Cadillac Records, and Top Five, as well as some incredible roles in hit TV shows including The West Wing, Ugly Betty, and Flashforward among many others.
Most recently, Union has been enjoying success on the BET TV show Being Mary Jane, and she will be starring in the lead role of the movie Breaking In, set to be released in May 2018.
8 Allison Janney (Ms. Perky)
Although Allison Janney isn’t in 10 Things I Hate About You for very long, her role as Ms. Perky steals the movie. But hey, that’s pretty much typical of Allison Janney, isn’t it? Put her in anything and she’ll shine brighter than anyone else. Her depiction of Ms. Perky as the aspirational romance novelist principal of the school is hilarious, and no one could have delivered the lines quite like she did.
Before 10 Things I Hate About You, Janney was already a seasoned actress with a roster of credits to her name. In 1999 alone, the same year that 10 Things came out, Janney was also starring in The West Wing as C.J Cregg, a part which won her four of her seven Emmys, as well as starring in the Academy Award-winning movie American Beauty.
Janney has had a hugely successful career over the years, and has starred in other major films and TV shows, including The Help, The Hours, Miss Peregrine's Home for Peculiar Children, and many others.
Of course, Janney’s latest triumph was her Oscar-win for her supporting role in I, Tonya, a part which captivated all audiences of the film and for which she certainly deservedly her golden statue.
7 Larry Miller (Walter Stratford)
Larry Miller is best known for his teen rom-com roles, and aside from his unforgettable role as Kat and Bianca’s father Walter Stratford in 10 Things I Hate About You, he’s probably best known for his role playing Paolo, the sassy stylist in The Princess Diaries films.
Larry Miller’s list of credits is exceptionally long, with many TV and film appearances under his belt. However, no one who grew up in the 1990s and 2000s will ever not think of him as the strict father figure in 10 Things who forced his daughters to wear a faux pregnancy tummy in order to learn the important lesson of abstinence.
Since appearing in 10 Things I Hate About You, Larry Miller’s biggest roles have been in 8 Simple Rules, Law and Order, and the previously mentioned Princess Diaries movies.
He also reprised his role as Walter Stratford in the short-lived TV series 10 Things I Hate About You, based on the movie.
Most recently, Miller has acted in the TV mini-series High School Cupid, a Cupid Inc. Story and has two movies in which he has a part which are currently in post-production, including Second Act starring Jennifer Lopez, Milo Ventimiglia, and Vanessa Hudgens.
6 Daryl Mitchell (Mr. Morgan)
Daryl Mitchell was absolutely brilliant as Mr. Morgan in 10 Things I Hate About You, the unconventional English teacher in whose class we witnessed Kat break her icy front while reading an emotional poem to Patrick. Any kid who watched the movie is sure to have wished they had a teacher like Mr. Morgan, who told it like it was and wasn’t about to put up with any of his students’ shenanigans.
Before his role in the film, Daryl Mitchell had been working in film and TV since 1990, having made appearances on The Cosby Show, Law & Order, The Fresh Prince of Bel-Air, and The John Larroquette Show. Post 10 Things I Hate About You, Mitchell went on to appear in cult classic Galaxy Quest and he had a recurring part in Veronica’s Closet until 2000.
However, in 2001 Daryl Mitchell experienced a tragic motorcycle accident that paralyzed him permanently from the waist down.
Once bound to a wheelchair, it seems that Mitchell found some difficulty in being cast for as many projects as he was getting before, making his acting career somewhat limited.
Despite his accident though, Mitchell persevered with his desire to act and scored a number of parts, mostly in TV shows. These include Ed, Brothers, and most recently NCIS: New Orleans.
5 Kay Hanley (as herself in band Letters to Cleo)
Aside from the great story and admirable acting in 10 Things I Hate About You, one of the best things about the movie is its soundtrack. Very much mirroring the music Kat loves listening to, the film’s soundtrack features a whole host of iconic '90s bands including Salt-N-Pepa, The Notorious B.I.G., Save Ferris, and Letters to Cleo.
In fact, Kay Hanley, the lead singer of Letters to Cleo, makes a cameo appearance in the club scene and at the end of the film during the high school prom. Hanley performs “Cruel to be Kind” with a ska band, which in the movie we are led to believe is arranged by Patrick especially for Kat, since Letters to Cleo is her favorite band.
Letters to Cleo were big in the 1990s, but the band disbanded in 2000. They did reunite in 2016 and released an EP called “Back to Nebraska”, but since then, it’s been pretty quiet in terms of the band as a whole and for Kay as a soloist too.
However, 10 Things I Hate About You and its continued popularity have certainly led to many people discovering and rediscovering this awesome band, giving Letters to Cleo an even bigger legacy than they might have had without this now-cult film.
4 Kyle Cease (Bogey Lowenstein)
Ah, Bogey Lowenstein, the unsuspecting wine and cheese guy whose house got trashed in one of TV’s greatest-looking high school parties. Although technically we didn’t really need Bogey Lowenstein to be the way he was for the movie to work, we’re sure glad we got him as he added that extra bit of hilarious contrast to the other students we got to meet throughout the movie. Clearly the high school in 10 Things I Hate About You had some very niche groups of people, and although we might not all be able to relate to these particular social group distinctions from our own high school experiences, it sure did make for a fun movie.
Bogey Lowenstein was actor Kyle Cease’s first on-screen role, and it seems that he hasn’t done all that much since.
Two years after 10 Things, Cease went on to appear in Not Another Teen Movie but apart from that, his other acting credits appear to be in random, not very known TV shows.
However, even though Kyle Cease hasn’t been tearing it up on our screens, he has been busy in other ways. Not only is he a New York Times best-selling author for his book I Hope I Screw This Up, he’s also gained notoriety as a stand-up comedian, and, based on all of his life experiences in show businesses and comedy, he’s also a transformational speaker. Not bad Bogey, not bad at all.
3 Monique Powell (as herself in band Save Ferris)
Another great band from the 1990s highlighted in 10 Things I Hate About You is Save Ferris. At the end of the movie during the prom scene, lead singer of Save Ferris, Monique Powell, sings "Cruel to be Kind" alongside Letters to Cleo front-woman Kay Hanley. The prom scene is one of the best moments in the film, not only for the great musical performances but also, of course, because that’s when Bianca punches Joey straight in the nose.
Save Ferris, whose name comes from the '80s classic movie Ferris Bueller’s Day Off, formed in 1995 and, despite a ten-year hiatus between 2003 and 2013 and multiple changes to the band’s lineup, is still going strong today.
In February 2017, Save Ferris released their first EP in 18 years called “Checkered Past”.
Save Ferris was an incredibly important band in the 1990s, not only for their original ska rock sound, but also for being one of the few ska rock bands to be fronted by a woman. Monique Powell’s voice was the soundtrack to a generation, and their notoriety for great music still lives on and continues to inspire people. Again, thanks to 10 Things I Hate About You, a wider audience probably got introduced to this great band, and we can all be grateful for this movie’s superb selection of tunes.
2 David Leisure (Mr. Chapin)
David Leisure’s role as Mr. Chapin was unconventional to say the least. The detention scene with the packet of Cheetos is one of the more bizarre moments in the movie, and we’re not sure if Kat flashing him would make it into a 2018 edit of the movie. It wasn’t exactly the most believable of episodes in the film, but then again, how likely is it that the school’s bad boy hunk would serenade you with “Can't Take My Eyes Off Of You ”?
David Leisure had already been acting since the 1980s before getting his role as Mr. Chapin in 10 Things I Hate About You, and his list of movie credits before this film include Airplane!, Airplane II: The Sequel and The Brady Bunch Movie, as well as a whole host of TV appearances in shows such as ALF, Married with Children, and The Golden Girls. The same year 10 Things I Hate About You came out, Leisure was also appearing in six television series, so clearly he was a busy man.
After 10 Things I Hate About You was released, David Leisure continued to work in TV and film, with his most notable roles being in the daytime soap operas The Young and the Restless and Days of Our Lives. Leisure hasn’t been in anything in since 2015 however, so evidently he has finally given into his name and is hopefully enjoying some good Leisure time.
1 Heath Ledger (Patrick Verona)
One of the brightest stars the world lost all to soon was, of course, Heath Ledger, who tragically passed away in 2008, at only 28 years old. Known for both his pretty boy looks as well as his striking talent as an actor, Ledger was a singular star who pushed the limits of his craft as well as his own self.
One of his best known and most loved roles was as Patrick Verona in 10 Things I Hate About You, where we collectively fell in love with his character who turned from edgy bad boy into the boyfriend we all secretly hoped to be and/or be with. Heath Ledger’s role in 10 Things was his first real breakout role in film, having previously gained fame from the Australian TV series Home and Away. His impressive and varied filmography shows someone who wasn’t afraid to take risks, and whose dedication to cinema and acting seemed to have no bounds.
Heath Ledger’s final on-screen performance was in The Imaginarium of Doctor Parnassus, released in 2009, although he of course became most famous for his portrayal of The Joker in The Dark Knight. No one will ever forget his magnetizing spin on the infamous Batman villain, a role for which he posthumously received an Oscar for Best Supporting Actor.
Who was your favorite character in 10 Things I Hate About You? Let us know in the comments!