If you grew up during the peak Disney Channel era, you probably remember Jackson Stewart as the goofy, cheese-jerky-loving older brother who was constantly getting roasted by Miley. He felt like every other high schooler on TV—maybe a little shorter, definitely more chaotic, but fundamentally a kid.
Except he wasn't.
Honestly, the "Hannah Montana" Jason Earles situation is one of those Hollywood facts that breaks your brain the more you think about it. While Jackson was navigating the perils of learner's permits and high school crushes, the actor playing him was closer to his mid-life crisis than his middle school graduation. It's a classic case of "Disney Magic" meeting biological reality, and once you see the numbers, you'll never watch the reruns the same way again.
The Age Gap That Shocked the Fandom
Let’s get the stats out of the way because they are wild. When Hannah Montana premiered in 2006, Miley Cyrus was 13 years old. Her character, Miley Stewart, was roughly the same age. Jason Earles was playing Jackson Stewart, a 16-year-old.
In reality? Jason Earles was 29.
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Think about that for a second. By the time the show wrapped its final season in 2011, Jason was 34 years old. He was playing a teenager while being only 15 years younger than Billy Ray Cyrus, the man playing his father. To put it in an even weirder perspective, Jason is actually only three days younger than WWE legend John Cena. When Cena guest-starred on the show, they looked like two different generations, yet they were born in the same week of April 1977.
Why Nobody Noticed
Usually, when a 30-year-old plays a teen (looking at you, Grease), it's painfully obvious. You see the crows-feet or the receding hairline and just sort of "agree" to believe the lie. But Jason actually pulled it off.
A big part of this was a condition he has called Kallmann syndrome. It’s a rare genetic condition that essentially delays or prevents the onset of puberty by affecting the production of certain hormones. For Jason, this meant he retained a youthful face, a higher voice, and a smaller stature (he's about 5'5") well into his adult years. While he's mentioned in interviews that looking like a kid was sometimes a "blessing and a curse" in his personal life, in the world of Hollywood, it was a golden ticket.
How He Almost Lost the Role to a Puppet
This is a piece of Hannah Montana trivia that sounds like a fever dream but is 100% true. In the very early stages of development, the character of Jackson was completely different.
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Jason recently revealed on the Magical Rewind podcast that in the original pilot script, Jackson was a shy, introverted kid who couldn't handle his sister's fame. His coping mechanism? Talking through an orangutan hand puppet.
"It was awful," Earles admitted. He actually spent days working with a professional puppeteer to get the movements right. It wasn't until a few days before filming the pilot that the writers saw Jason and Miley bantering and making fun of each other in the kitchen. They realized the "annoying older brother" vibe was way more relatable and funny than a guy with a puppet. They scrapped the orangutan three days before the cameras rolled, and the Jackson Stewart we know was born.
Life After the Wig: What Happened to Jason?
After the show ended, Jason didn't just disappear into the Disney vault. He stayed within the Mouse House ecosystem but moved into roles that actually matched his maturity—even if he still looked like he could be in college.
- Kickin' It: He played Sensei Rudy Gillespie on the Disney XD series for four seasons. This was a pivotal move because he also started directing episodes, proving he had more than just comedic timing.
- Mentoring: He eventually transitioned into a behind-the-scenes role as an acting coach. Most notably, he worked with the cast of High School Musical: The Musical: The Series, helping stars like Olivia Rodrigo and Joshua Bassett navigate the same Disney machine he survived.
- The Disney Channel Games: He was basically the MVP of these summer specials, appearing as a leader for the Blue and Red teams across multiple years.
Why the "Hannah Montana" Jason Earles Legacy Matters
A lot of people find the age gap "creepy" in retrospect, but it’s actually a testament to his talent. Being nearly 30 and keeping up with the energy of a 13-year-old Miley Cyrus is exhausting work. He had to match her slapstick energy without making it feel like an adult was mocking a child.
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His presence on set also provided a stable anchor for the younger cast. He was an adult who understood the industry, which likely helped when the show became a global phenomenon and the pressure on the kids became immense.
Actionable Takeaways for Fans and Creators
- Don't trust the "teen" look: Hollywood often hires adults to play teens because they can work longer hours without the strict labor laws that apply to minors. If a teen character looks 25, they probably are.
- Watch the early seasons again: Now that you know he's 29, watch his physicality. He uses high-energy movements and specific vocal inflections to mask his actual age.
- Follow his directing work: If you're a fan of sitcom structures, Jason's episodes of Kickin' It show a clear understanding of the "Disney formula" from someone who lived it for a decade.
If you’re diving back into a nostalgia binge, pay attention to the scenes between Billy Ray and Jason. Knowing they are only 15 years apart makes their "father-son" talks feel like two guys who could have gone to the same high school at the same time. It's a testament to the makeup team, Jason's genetics, and the fact that in Hollywood, age really is just a number on a casting sheet.
To see how Jason looks today, you can find him on Instagram where he frequently shares throwbacks and updates on his current directing projects.