When Hannah Montana premiered on Disney Channel in March 2006, viewers met Jackson Stewart—the goofy, scheming older brother of Miley Stewart. Jackson was supposed to be around 15 or 16 years old. But the actor playing him, Jason Earles, had a secret: he was actually 29 years old.

Born on April 26, 1977, Earles was nearly three decades old when he first donned Jackson's signature bowling shirts and pulled off the antics of a high school slacker. By the time the show wrapped in 2011, he was 34, still convincingly playing a character who had aged to only 23.

Hollywood's Worst-Kept Secret

The age gap became one of Disney Channel's most fascinating casting choices. While Miley Cyrus was actually a teenager (13 when the show started), her on-screen older brother was old enough to have been her real-life parent. Yet somehow, it worked.

Earles' youthful appearance and comedic timing made the illusion seamless. Fans had no idea they were watching someone who could have graduated high school before some of the show's youngest viewers were even born. The casting choice wasn't unusual for Hollywood—playing younger has always been a thing—but the nearly 15-year age difference between actor and character was extreme even by industry standards.

Why Cast Older?

There are practical reasons networks prefer adult actors for teen roles:

Labor laws: Adult actors can work longer hours without restrictions on minors
Consistency: No awkward growth spurts or voice changes mid-season
Experience: Professional maturity for demanding shooting schedules
Reliability: No need for on-set tutors or parent supervision

For a show filming multiple episodes back-to-back, having a seasoned 30-year-old actor instead of an actual teenager made production smoother. Earles delivered consistent performances without the unpredictability of adolescence.

The Legacy

Jason Earles' portrayal of Jackson Stewart became iconic precisely because viewers never questioned it. His commitment to the role—from physical comedy to perfect timing—proved that age is just a number when the performance is right. The show ran for 98 episodes across four seasons, and Jackson remained a fan-favorite character throughout.

Today, the revelation that Jackson was played by someone pushing 30 is a fun piece of Hannah Montana trivia. It's a testament to Earles' talent that an actor born in 1977 could make millions of viewers believe he was just another teenager navigating high school drama.

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