Jason Earles is an actor, comedian and director best known for playing Jackson Stewart on Disney’s Hannah Montana.
If you grew up watching Disney Channel in the 2000s, chances are Jason was a huge part of your childhood.
In this episode, Jason takes us behind the scenes of one of Disney Channel’s most iconic shows as we celebrate its 20th anniversary this year. He opens up about the surprising story behind landing the role of Jackson, working alongside Miley Cyrus and Billy Ray Cyrus, finding his character’s comedic voice, and what it was really like saying goodbye after four seasons and 101 episodes.
Jason also reflects on revisiting Hannah Montana two decades later through his podcast, Best of Both Our Worlds, and shares what has surprised him most about watching the series back. Beyond Jackson Stewart, we dive into his journey as an actor, his work mentoring the next generation of Disney talent, his transition into directing, the challenges that shaped him and what he’s most excited about in this next chapter.
Plus, we have some fun along the way — including Jason’s most embarrassing moment, irrational fears, favorite memories from the show, Jackson’s biggest red flag, and what he thinks Jackson’s Instagram bio would say today!
It’s a nostalgic, funny and honest conversation with the man behind one of Disney Channel’s most unforgettable characters.