Honestly, it’s been over twenty-five years since Patrick Verona sat on those stadium bleachers and got serenaded by a marching band. Twenty-five years. Let that sink in for a second. When we talk about the 10 Things I Hate About You actors, we aren't just talking about a cast that got lucky with a Shakespearean adaptation; we're looking at a group of people who essentially defined the "cool" DNA of the late nineties.
They weren't just faces on a poster. They were icons.
The movie was basically The Taming of the Shrew but with more Doc Martens and letters of intent for Sarah Lawrence. But the real magic wasn't just the script. It was the specific lightning-in-a-bottle energy of the ensemble. Some of them became Oscar winners. Others walked away from the spotlight entirely. A few, heartbreakingly, aren't with us anymore.
If you grew up watching Kat Stratford snap at her English teacher, you probably feel like you know these people. But their paths since 1999 have been anything but predictable.
The Ledger Legacy: More Than Just a Grin
Heath Ledger. Just saying the name feels heavy now. Before he was the Joker, before he was Ennis Del Rio, he was just a kid from Australia with a thick accent and a smile that could actually melt a camera lens.
He didn't want to be a teen heartthrob. That's the part people forget. After the movie blew up, Ledger was offered every "pretty boy" lead in Hollywood. He turned them down. He almost went broke waiting for something that wasn't a rom-com. He wanted to be a "serious" actor, and eventually, the world caught up to his ambition. His work in Brokeback Mountain changed the industry. His performance in The Dark Knight changed cinema history.
📖 Related: Big Brother 27 Morgan: What Really Happened Behind the Scenes
When he passed away in 2008, it felt like the air went out of the room. He remains the emotional heartbeat of the 10 Things I Hate About You actors, the one who proved that "teen movies" could be a launchpad for genuine greatness.
Julia Stiles and the Art of the Quiet Career
Julia Stiles was the only person who could have played Kat. Period. She had this intellectual sharpness that didn't feel scripted; it felt like she was actually annoyed by everyone around her.
What's cool about Julia is that she didn't chase the blockbuster dragon forever. Sure, she was a massive part of the Bourne franchise, playing Nicky Parsons with a subtle, evolving grit. But she also went back to school. She studied English Literature at Columbia University while she was one of the biggest stars on the planet. Think about that. Most people would be at parties; she was in a library.
Recently, she’s been killing it in the series Riviera and had a scene-stealing role in Hustlers. She’s also stepped behind the camera to direct. She’s the blueprint for how to have a long-term career without losing your mind to the paparazzi machine.
The Joseph Gordon-Levitt Evolution
If you look at Cameron James in 10 Things, he’s so... earnest. He’s the "nice guy" who actually wins. Joseph Gordon-Levitt was already a veteran by then because of 3rd Rock from the Sun, but this movie showed he could carry a film.
👉 See also: The Lil Wayne Tracklist for Tha Carter 3: What Most People Get Wrong
He took a break too. He went to Columbia (must be something in the water on that set) and then came back to become the king of the indies. From 500 Days of Summer to Inception, Joe—as everyone calls him—became a symbol of the modern polymath. He started HitRecord, a collaborative media platform. He directed Don Jon.
He doesn't look like that floppy-haired kid anymore, but that same "I'll do whatever it takes to get the girl/save the day" energy is still there in his performances.
Larisa Oleynik: The Girl Next Door Gone Rogue
Bianca Stratford was supposed to be the shallow one, but Larisa Oleynik gave her a spine. Larisa was already huge from The Secret World of Alex Mack. She was the ultimate nineties "it girl."
After the movie, she didn't disappear, but she definitely stepped back from the "leading lady" frenzy. She’s been a working actor’s actor. You might have spotted her in Mad Men as Ken Cosgrove’s wife or in Pretty Little Liars. She does a lot of theater too. Honestly, she seems like one of the most well-adjusted people to ever come out of that era of teen stardom.
The Supporting Players Who Stole the Show
You can't talk about the 10 Things I Hate About You actors without mentioning the people in the margins.
✨ Don't miss: Songs by Tyler Childers: What Most People Get Wrong
- David Krumholtz (Michael): He’s a legend. From The Santa Clause to Numb3rs to Oppenheimer. Yes, he was in Oppenheimer. He’s become one of the most respected character actors in the business.
- Gabrielle Union (Chastity): This was just the beginning for her. Bring It On happened a year later, and she’s now a mogul, an author, and a massive advocate for inclusion in Hollywood. She literally doesn't age. It’s suspicious.
- Andrew Keegan (Joey Donner): The ultimate "eat me" guy. He became a bit of a meme later in life when he started a spiritual center called Full Circle in Venice Beach. It was very "California," and the internet had a field day with it, but he seems happy.
- Allison Janney (Ms. Perky): She had about five minutes of screen time and stole every single second. She’s won Oscars and Emmys since then. She’s basically acting royalty.
The Director's Vision
Gil Junger directed this thing, and he’s often the unsung hero. He allowed the actors to improvise. That poem Kat reads at the end? Julia Stiles actually cried. It wasn't in the script for her to break down like that, but Junger kept the camera rolling. That's why it feels real. That's why we’re still talking about it.
Why This Cast Still Matters Today
Most teen movies from 1999 are unwatchable now. They’re cringey or dated. But this one holds up because the cast was overqualified for the material. They treated a high school comedy like it was high art.
They weren't just "actors." They were a collection of personalities that perfectly mirrored the friction of being a teenager—the desire to be cool vs. the desire to be yourself.
Actionable Steps for Fans and Collectors
If you’re looking to dive deeper into the world of these actors, don't just re-watch the movie on a loop. Here is how to actually engage with their legacies:
- Watch the "Serious" Pivot Films: To see the range of these actors, watch Ledger in Candy, Stiles in Business of Strangers, and Gordon-Levitt in Brick. It reframes how you see their performances in the 1999 film.
- Track the Shakespearean Roots: If you’re a film nerd, watch the 1967 version of The Taming of the Shrew with Elizabeth Taylor. It makes the "Easter eggs" in 10 Things much more rewarding.
- Support Current Projects: Follow Julia Stiles’ directorial debut Wish You Were Here or Joseph Gordon-Levitt’s continued work on HitRecord. Supporting their current evolution is the best way to honor the nostalgia.
- Look for the Anniversary Screenings: Many independent theaters run 35mm screenings of the film for its anniversaries. The chemistry between Ledger and Stiles hits differently on a massive silver screen.
The reality is that we'll never get another cast quite like this. It was a specific moment in time when the industry was willing to take a chance on a bunch of "nobodies" who turned out to be the future of Hollywood. They grew up, and so did we.
For those looking to build a collection of 90s cinema, focusing on the filmography of these specific performers provides a comprehensive map of the transition from the indie boom to the modern blockbuster era.