The Shocking Truth: 5 Things You Never Knew About Jason Earles, The ‘Brother On Hannah Montana’ Who Felt ‘F***ed’ By Disney
Few characters define a generation of Disney Channel viewers quite like Jackson Stewart, the perpetually goofy and lovable older brother of Miley Stewart/Hannah Montana. The actor behind the iconic role, Jason Earles, brought a chaotic energy and comedic genius to the show from 2006 to 2011, creating one of the most memorable sibling dynamics in sitcom history. However, the story of Jason Earles is far more complex and surprising than his on-screen persona suggests, especially given the recent, candid revelations about his time at the Disney Channel.
As of late 2025, Earles remains a prominent figure in the industry, but his focus has shifted dramatically. He has transitioned from being a star in front of the camera to a powerhouse behind it, focusing on directing and coaching the next generation of young actors. The biggest headline, however, is the shocking May 2025 revelation where Earles opened up about the "harsh reality" of his original Disney contract, a candid admission that has stunned fans and reignited conversations about the treatment of child stars and young talent in Hollywood. This deep dive uncovers the man behind Jackson Stewart, his career trajectory, and the surprising truths he’s finally sharing.
Jason Earles: Full Biography and Profile
Jason Daniel Earles is an American actor, comedian, director, and martial artist best known for his long-running roles on the Disney Channel. His career spans over two decades, transitioning successfully from acting to a respected mentorship role within the industry.
- Full Name: Jason Daniel Earles
- Date of Birth: April 26, 1977
- Place of Birth: San Diego, California, U.S.
- Current Age (as of 2025): 48 years old
- Education: Rocky Mountain College (B.A.)
- Notable Roles: Jackson Stewart in Hannah Montana (2006–2011), Rudy Gillespie in Kickin' It (2011–2015), Dewey Wood in High School Musical: The Musical: The Series (2022)
- Spouses: Jennifer Earles (m. 2002; div. 2013), Katie Drysen (m. 2017)
- Career Niche: Acting coach and director for younger talent
The Age Controversy: Why Jackson Stewart Was 28
One of the most persistent and mind-boggling facts about Hannah Montana is the significant age difference between Jason Earles and the character he played. This detail often resurfaces, shocking new generations of fans.
The 12-Year Gap That Broke the Internet
When Hannah Montana first premiered in 2006, the character Jackson Stewart was meant to be a typical, goofy teenager, only a few years older than his sister Miley Stewart (Miley Cyrus).
However, Jason Earles was born in 1977, making him 28 years old when the show began.
Miley Cyrus, born in 1992, was only 13 at the time. This meant there was a 15-year age gap between the on-screen siblings, and a 12-year gap between Earles and the character's intended age.
Earles’ ability to convincingly portray a teenager for five years, even into his mid-30s, is a testament to his comedic acting skills and youthful appearance. The internet continues to be stunned by this fact, making it a permanent piece of Disney Channel trivia and a major source of topical authority for his career.
From Disney Star to Directing Mentor: Jason Earles’ Career Evolution
Following the end of Hannah Montana in 2011, Earles successfully avoided the common pitfalls of typecasting by immediately jumping into another long-running Disney XD series, Kickin' It.
On Kickin' It, he played Rudy Gillespie, the eccentric sensei of the Bobby Wasabi Martial Arts Academy, a role that allowed him to continue showcasing his physical comedy and martial arts background.
A New Niche: Coaching and Directing
In the years since his major acting roles, Jason Earles has found a significant new niche as a director and acting coach, a role he has fully embraced as of 2025.
He leverages his extensive experience from both Hannah Montana and Kickin' It to mentor and guide younger talent, helping them navigate the unique pressures of the industry.
His work is often focused on helping new Disney stars and other young actors hone their craft, providing them with a wealth of practical knowledge that only a Disney veteran can offer.
He has also returned to the screen in a recurring role as Dewey Wood in the Disney+ series High School Musical: The Musical: The Series, a nod to his Disney roots while working with a new generation of performers.
The May 2025 Contract Revelation: 'I Got F***ed'
Perhaps the most compelling and current update on Jason Earles is his candid discussion about the financial realities of his time on Hannah Montana, an interview that made headlines in May 2025.
The 'Worst Contract Ever'
Earles openly discussed the restrictive and financially unfavorable contract he signed with Disney Channel early in his career.
In a direct quote that resonated across the entertainment world, he stated that he felt he "got f***ed" by the terms of his original agreement.
This revelation speaks to a larger, ongoing conversation in Hollywood about residuals, contract fairness, and the often-harsh business side of children's television, especially for actors who sign on early in their careers without significant leverage.
His honesty about the "harsh reality behind his Disney pay" provides a crucial, unfiltered perspective from a former Disney star who is now in a position to speak freely.
Jason Earles’ Post-Disney Filmography and Entities
While Jackson Stewart and Rudy Gillespie are his most famous entities, Earles has a diverse filmography that establishes his topical authority in both comedy and independent cinema. His ability to move between major network television and smaller projects shows a dedicated, working actor.
- Major TV Roles:
- Hannah Montana (2006–2011) as Jackson Stewart
- Kickin' It (2011–2015) as Rudy Gillespie
- High School Musical: The Musical: The Series (2022) as Dewey Wood
- Film Appearances:
- National Treasure (2004)
- American Pie Presents: Band Camp (2005)
- Hannah Montana: The Movie (2009)
- Super Buddies (2013)
- Second Chances (2023) as Taco Tom (Post-production)
- Directing and Coaching:
- His directorial work includes episodes of Disney XD's Kickin' It and other projects, solidifying his role behind the camera.
- He is recognized as a notable acting coach, mentoring stars on set and through workshops.
The story of Jason Earles is a fascinating case study in Hollywood longevity. He navigated the intense scrutiny of the Disney machine, survived the viral shock of his true age, and is now using his experience to shape the careers of others. His recent transparency regarding his contract has cemented his status not just as a nostalgic figure, but as an important voice advocating for fairness in the entertainment industry. The legacy of Jackson Stewart is secure, but the future of Jason Earles as a director and mentor is arguably more impactful.
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