Jason Earles: Disney Star’s Evolution from Actor to Mentor and Back to Screen

A Lasting Legacy in Disney Entertainment

Jason Daniel Earles, the American actor widely recognized for his role as Jackson Stewart in the Disney Channel sitcom Hannah Montana and Rudy Gillespie in Disney XD’s Kickin’ It, has evolved his career in remarkable ways.

Behind the Scenes Mentor

Beyond his success as an actor, Earles has made significant contributions to High School Musical: The Musical: The Series, serving as an acting coach for the show’s first two seasons. In this role, he has functioned as a mentor to the newer actors on the set.

The connection between Earles and the young cast runs deep, as many of them grew up watching Hannah Montana and were fans of his work. The cast frequently suggested that he should appear in the show, even if just as a background character like a janitor or a teacher walking through the hall.

Return to the Screen

Earles has now taken on the role of camp director Mr. Dewey Wood in the series. His character is described as a very curmudgeonly guy who likes to kill the joy in any situation he’s around – as Earles puts it, ‘you’ve never seen anybody love to hate being someplace as much as Dewey does.’

The role has created what Earles describes as a ‘meta and bizarre’ dynamic, reminiscent of Disney Channel’s early crossover episodes. This unique situation has led to interesting moments on set.

Personal Life and Current Projects

In his personal life, Earles was married to Jennifer Earles from 2002 to 2013, and later married Katie Drysen on August 12, 2017. He maintains an active social media presence with 238,000 followers on Instagram, where he shares updates about his upcoming shows and projects.