7 Shocking Facts About Jackson Of Hannah Montana: What Jason Earles Is Doing Now (2025 Updates)
Few characters define the Disney Channel era quite like Jackson Stewart, the goofy, perpetually hungry older brother of Miley Stewart (Miley Cyrus) on Hannah Montana. The actor behind the iconic role, Jason Earles, has successfully navigated the transition from a beloved sitcom star to a multi-faceted director, producer, and acting coach in the entertainment industry. As of late 2024 and heading into 2025, Earles continues to make waves, taking on new, surprising roles both in front of and behind the camera, proving his career is far from over.
The biggest surprise for many fans remains the vast age difference between the actor and the teenager he played—a fact that has recently resurfaced and stunned a new generation of viewers. Below, we dive into the latest updates on Jason Earles's life, his surprising new movie roles, his directorial work, and a complete look at his career trajectory since leaving Malibu.
Jason Earles: Complete Biography and Profile
Jason Earles, the actor best known as Jackson Stewart, has a diverse background in acting, comedy, and even martial arts. His career spans over two decades, with a significant portion dedicated to the Disney brand.
- Full Name: Jason Daniel Earles
- Date of Birth: April 26, 1977
- Place of Birth: San Diego, California, U.S.
- Education: Rocky Mountain College, Billings, Montana (B.A. in Theatre Arts)
- Profession: Actor, Comedian, Director, Producer, Martial Artist
- Years Active: 2003–Present
- Spouse(s): Jennifer Earles (m. 2002; div. 2013); Katie Drysen (m. 2017)
- Notable Roles: Jackson Stewart (*Hannah Montana*), Sensei Rudy Gillespie (*Kickin' It*), Dewey Wood (*HSMTMTS*)
- Net Worth: Estimated at $8 Million
- Key Milestone: Nominated for a Teen Choice Award in 2009 for his role in *Hannah Montana*.
The Shocking Age Reveal and Transition to Directing
One fact about the production of Hannah Montana that continues to generate buzz is the age of Jason Earles during the show's run. When the series premiered in 2006, Earles was 29 years old, playing the 16-year-old older brother, Jackson Stewart.
This age difference, which meant he was significantly older than his on-screen sister, Miley Cyrus, became a famous piece of Disney trivia. Earles has embraced the humor of the situation, often noting the surreal experience of playing a high schooler well into his 30s.
From Comic Relief to Disney Director
After the four-season run of Hannah Montana concluded in 2011, Earles immediately transitioned to another major Disney XD hit, Kickin' It. In this series, he played Sensei Rudy Gillespie, the eccentric owner and sensei of the Bobby Wasabi Martial Arts Academy.
More importantly, this period marked his pivot to behind-the-scenes work. Earles began directing episodes of Kickin' It, eventually accumulating numerous directing credits across various Disney and non-Disney shows. His experience on set, which he has described as wanting to create a "safe environment" for the younger cast, proved invaluable for this new phase of his career.
His directorial work includes episodes of:
- *Kickin' It*
- *Gamer's Guide to Pretty Much Everything*
- *WTH: Welcome to Howler*
- *Dwight in Shining Armor*
Jason Earles’s Freshest Roles and 2025 Projects
Jason Earles has been consistently busy, with his most recent credits demonstrating a commitment to both acting and coaching, often within the Disney universe that launched his fame. His involvement in one of Disney's most popular modern franchises highlights his continued relevance.
1. Return to Disney in *HSMTMTS* (2022)
Earles made a notable return to the Disney ecosystem by joining the cast of *High School Musical: The Musical: The Series* (HSMTMTS) in Season 3.
He played the role of Dewey Wood, the quirky and enthusiastic camp director of Camp Shallow Lake. Beyond his on-screen role, Earles served as an acting coach for all four seasons of the series, mentoring the new generation of Disney stars.
2. Upcoming 2025 Film Role: *Worst Man*
Looking ahead to 2025, Earles is set to appear in the movie *Worst Man*. This project, along with other recent film credits, showcases his move into independent and feature film work, stepping away from the long-form sitcom format.
3. Recent Filmography (2023–2024)
His film career remains active, with two recent projects of note:
- *Second Chances* (2023)
- *Combat Radios A Christmas Carol for a Cure* (2024)
These roles ensure that Jason Earles's career is constantly evolving, providing fans with fresh content well over a decade after *Hannah Montana* ended.
The Jackson Stewart Legacy and Cast Reunions
The character of Jackson Rod Stewart was more than just comic relief; he was the grounding force and the "normal" sibling to the superstar Miley Stewart. He was often seen working odd jobs, eventually securing employment as a video game tester in the series finale, "Wherever I Go."
His relationship with his father, Robby Ray (Billy Ray Cyrus), and his on-again, off-again girlfriend, Siena, were central to his storyline, providing a humorous contrast to Miley's double life as Hannah Montana.
A Disney Channel Reunion
The bond forged on the Disney set remains strong. In 2017, Jason Earles married his longtime girlfriend, Katie Drysen, at a beautiful ceremony in Toluca Lake.
The wedding was a mini-Disney Channel reunion, with several former co-stars in attendance, including Emily Osment (Lilly Truscott), Moises Arias (Rico), and even his *Kickin' It* castmates.
Furthermore, Earles has been a part of several recent *Hannah Montana* cast reunions, including one notable gathering with Emily Osment, Mitchel Musso (Oliver Oken), and Moisés Arias. While a full series reboot remains unlikely—especially without the full participation of Miley Cyrus—Earles has publicly commented that he believes a reunion is possible, showing his continued affection for the show that defined his early career.
From playing an over-aged teenager who loved his chicken wings to directing and coaching the next wave of talent, Jason Earles's journey is a testament to longevity and versatility in Hollywood. His latest projects confirm that the man who played Jackson Stewart is now a respected figure shaping the future of family entertainment.
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