Jason Earles Spills the Tea on Miley Cyrus, Jackson’s Funniest Moments, and Hidden Easter Eggs

Jason Earles is celebrating two decades since Hannah Montana first aired, reflecting on his time playing Miley Cyrus’s older brother, Jackson Stewart. Earles, who was in his late 20s when the show began, shared that many of Jackson’s funniest moments were improvised — including his iconic falls and quirky catchphrases.

Bond With Miley Cyrus

Earles spoke fondly about his on-screen relationship with Miley, describing their sibling dynamic as adversarial but deeply protective. “I really love anytime Jackson got to have a heart-to-heart with Miley,” he said, noting those moments felt authentic and true to their bond.

Favorite Jackson Memories

Among his favorite memories are Jackson’s pogo stick antics, the “cheese jerky” song, and mimic fights that became fan favorites. Earles also revealed that he snuck in Easter eggs from his favorite films, including Tootsie and Back to the Future.

The Show’s Impact

Earles recalled realizing the show’s massive reach when fans began approaching him at the gym. He admitted that the series’ success and cultural impact still surprise him today. “Sweet niblets! I’m old!” he joked when reflecting on the 20-year milestone.

Cast Connections and New Projects

Though the cast doesn’t see each other often, Earles said they remain happy to reconnect whenever possible. He has also launched a Hannah Montana podcast, revisiting the show’s legacy and sharing behind-the-scenes stories with fans.

A Legacy of Laughter

Earles expressed gratitude for the opportunity to entertain a generation. “Thank YOU, Jason and the cast, for providing us with endless hours of entertainment growing up,” he said, acknowledging the enduring love for the Disney Channel classic.