THEN AND NOW: The cast of '10 Things I Hate About You'

Kat's antisocial attitude kept her friend group small and angered her younger sister, Bianca, who wasn't allowed to date until Kat did. Boys were afraid of Kat, which made it difficult for Bianca to find someone to date her sister. 

Stiles, 44, broke out thanks to her role in "10 Things I Hate About You" and went on to star in movies including "Save the Last Dance," "The Prince and Me," "Orphan," and "Silver Linings Playbook."

She's also known for playing Nicky in four "Jason Bourne" movies, starting with "The Bourne Identity."

She earned Golden Globe and Emmy nominations for starring on Showtime's "Dexter." 

In 2019, the actor starred alongside Jennifer Lopez in "Hustlers," portraying the real-life journalist who wrote the story that inspired the film. 

From 2017 to 2020, she starred on the British series "Riviera," and from 2022 to 2023, she starred on the Prime Video series "The Lake."

This year, she made her directorial debut with the romantic drama "Wish You Were Here," starring her "Orphan" costar Isabelle Fuhrman and Mena Massoud.

Stiles has been married to Preston Cook since 2017, and they have three children together.

Bianca wanted to date Joey, so she tried to find someone to date her sister. 

Of course, she ended up falling for sweet (if a bit conniving) tutor, Cameron.

Before "10 Things," Oleynik played the lead role on "The Secret World of Alex Mack," which arguably made her one of the most famous people in the cast at the time. The teen star was also on "Boy Meets World" and "Third Rock From the Sun." 

Oleynik, 44, has had a number of guest roles since starring in "10 Things," including "Mad Men," "Hawaii Five-0," "Pretty Little Liars," and "Law and Order: Special Victims Unit."

She also had a recurring role on the Netflix series "Trinkets," which was canceled after two seasons in 2020. Additionally, she pops up on Nickelodeon series frequently, such as "Erin & Aaron," "The Healing Powers of Dude," and "Winx Club."

He was hired to date Kat, but ultimately fell for her anyway. He also gave many teens unrealistic expectations of having their high school's token bad boy serenade them with Frankie Valli.

Ledger's career took off after "10 Things." He starred in movies including "A Knight's Tale," "Monster's Ball," "Lords of Dogtown," and "Casanova."

He earned his first Oscar nomination for "Brokeback Mountain" and won a posthumous Oscar for playing the Joker in "The Dark Knight."

His final role was in the movie "The Imaginarium of Doctor Parnassus." 

Cameron instantly developed a crush on Bianca and tried to win her affection by finding her older sister a date. Over the course of the film, he begins growing a bit of a backbone and even tells Bianca off for using him.

Before starring in "10 Things," Gordon-Levitt was known for "Angels in the Outfield," "Roseanne," and "Third Rock From the Sun."

The actor has since earned two Golden Globe nominations for starring in "(500) Days of Summer" and "50/50."

His other roles include "Inception," "The Dark Knight Rises," "Don John," "Sin City: A Dame To Kill For," and "Snowden."

In addition, the actor had voice cameos in "Star Wars: The Last Jedi," "Knives Out," and "Glass Onion," all directed by his friend Rian Johnson.

In 2020, he starred in the Netflix film "Project Power" alongside Jamie Foxx. He also had a role in the star-studded Aaron Sorkin film "The Trial of the Chicago 7."

Gordon-Levitt, 44, has been married to Tasha McCauley since 2014, and they have three children.

Joey agreed to go along with Cameron's scheme to get Patrick and Kat to date so he could date Bianca, but it all blew up in his face after Kat revealed how truly slimy he was.

Before "10 Things," Keegan, 46, starred on "Thunder Alley," "7th Heaven," and "Party of Five." Since then, he has had a few small roles on projects including "CSI: Crime Scene Investigation" and "Hollywood Darlings." 

Keegan made headlines in April 2014 when he was interviewed by New York Magazine after founding a new religion he called Full Circle. Almost a year later, its headquarters were raided by the California's Department of Alcohol Beverage Control for selling kombucha without a permit, per Vice.

"We weren't aware that we needed any sort of special license to sell kombucha," said a Full Circle spokesperson. Full Circle shut down in 2017.

In 2024, Keegan addressed rumors that he was a "cult leader" on an episode of "Pod Meets World," a podcast hosted by "Boy Meets World" stars Danielle Fishel, Rider Strong, and Will Friedle.

"Looking back, it was insane. I was putting down tens of thousands of dollars, but we opened it up and spent three years and really did build an amazing friend group," he said.

Keegan continued, "For all intents and purposes, it was a really cool community center for a bunch of people in Venice for a few years."

"I look back at it now and I'm like, I don't know anybody else who is being called a cult leader, so it's kind of like a badge of honor," he said.

Keegan did not respond to a request for comment from Business Insider.

Since 2017, Keegan has continued to act and even appeared on an episode of "Trinkets" alongside his "10 Things" costar Larisa Oleynik.

Keegan has one daughter, born in 2016.

Michael gave Cameron a tour of the school and helped him out with his plan to steal Bianca away from Joey.

Michael also got a sweet love story of his own, falling for Kat's friend Mandella.

Krumholtz, 47, was known for playing Bernard the Elf in "The Santa Clause" — an important character for many people — before starring in "10 Things I Hate About You." He reprised the role in "The Santa Clause 2" and "The Santa Clauses."

He's since appeared in "Harold and Kumar Go to White Castle," "Superbad," "Hail, Caesar!," and "The Ballad of Buster Scruggs." He has also starred on "Numb3rs," "The Good Wife," "Living Biblically," and "Poker Face."

In 2023, he played real-life scientist Isidor Isaac Rabi in "Oppenheimer," which went on to win best picture at the Academy Awards.

This year, Krumholtz will appear in "Springsteen: Deliver Me From Nowhere" and is set to costar with another David (David Corenswet, aka Superman) in "Mr. Irrelevant."

Krumholtz has been married to Vanessa Britting since 2010. They have two children.

She didn't end up being the best friend to Bianca — after they broke up, Chastity swooped right in to date Joey herself.

"10 Things" was only Union's second movie (the first being "She's All That"), but she had starred on shows like "7th Heaven," "Sister, Sister," and "Clueless" before then.

Union, 52, broke out in "Bring It On," and her 2000s movie roles included "Deliver Us From Eva," "Bad Boys II," and "Top Five." She also starred as the titular character on "Being Mary Jane."

This decade, Union appeared in a remake of "Cheaper by the Dozen," the Disney film "Strange World," "The Inspection," and "The Perfect Find."

Next year, she will have a voice role in the animated film "Goat" and will also appear in "The Casket Girls" and "Forbidden Fruits."

Outside acting, Union has been married to NBA star Dwyane Wade since 2014, and they welcomed their first child together, daughter Kaavia, via surrogate in 2018.

She memorably had an obsession with Shakespeare.

She starred in "Center Stage" and had minor roles on shows including "Charmed," "Private Practice," and "Masters of Sex."

Pratt, 51, was married to actor Kenneth Mitchell from 2006 until his death in 2024. He had been diagnosed with ALS in 2018, per People. They share two children.

Perky wrote erotic literature while at work.

Janney, 65, had already been working on-screen for 10 years when she was cast in "10 Things." Her breakout role on "The West Wing" earned the actor multiple Emmy wins.

Some of her other roles include "Hairspray," "Juno," "The Help," "Spy," and voicing Peach in "Finding Nemo" and "Finding Dory." Janney also appeared in 2019's "Bombshell," based on the Fox News scandal centered on Roger Ailes. 

She starred on the CBS sitcom "Mom" from 2013 to 2021.

Of course, she also won an Academy Award for playing Tonya Harding's mother, LaVona, in "I, Tonya."

Currently, Janney is starring on the Netflix series "The Diplomat" and the Apple TV+ series "Palm Royale."

Walter was an obstetrician and made Bianca wear a fake pregnancy belly to put her off dating in high school. He was the one who made the rule that Bianca could date … as soon as Kat did.

The comedian is best known for starring in movies like "Pretty Woman," "Runaway Bride," "The Princess Diaries," and "Get Smart." 

Miller, 71, has also guest-starred on shows like "Curb Your Enthusiasm," "Shake It Up," and "Hot in Cleveland."

He's been married to Eileen Conn, a TV writer, since the '90s. They have two children.

Mr. Morgan was an English teacher who, to put it lightly, did not suffer fools.

Mitchell, 60, is also known for starring on "The John Larroquette Show" and "Brothers" and in "Galaxy Quest" and "Inside Man."

In 2001, Mitchell was involved in a motorcycle crash in South Carolina. "It was totally my fault," Mitchell told People at the time. "I took off in the dark without a helmet on a road I didn't know."

The actor starred as Patton Plame on "NCIS: New Orleans" for seven seasons, and was on "Fear the Walking Dead" from 2018 to 2022.

Mitchell stars in the new ABC sitcom "Shifting Gears" alongside Tim Allen, Kat Dennings, and Seann William Scott.

He has four children with his wife, Carol.