Jason Earles is revisiting one of the more surprising behind-the-scenes stories from Hannah Montana — and it turns out he wasn’t the only one keeping a secret on set.
Speaking on the debut episode of the Best of Both Our Worlds podcast, released March 17, Earles revealed that he was 28 years old — and already married — when he auditioned to play Jackson Stewart, the teenage older brother of Miley Cyrus’s character. At the time, he told producers he was 18.
“I was desperately afraid that I was going to be fired and recast because I had a big secret,” Earles said, explaining that the role was written as a 16-year-old and he doubted anyone would believe his casting if his real age were known.
The decision to bend the truth, he said, was partly encouraged. Casting director Lisa London — who had previously been told a similar age adjustment by Earles — urged him to stick with the claim during auditions. The gamble paid off, and he ultimately landed the role.
Still, the actor admitted he spent much of the early production period worried the truth would surface. That moment came roughly halfway through the first season.
According to Earles and cohost Douglas Danger Lieblein, the secret wasn’t uncovered until around episode eight. Earles recalled being approached by a Disney executive during a taping night and asked directly about his age — and his personal life.
“I remember he said, ‘You’re 28? And you’re married?’” Earles said. “And I had to admit, yeah — the person I’d been seen with on set was my wife.”
Despite the tense exchange, the revelation didn’t cost him the role. Earles remained with the show for its entire four-season run from 2006 to 2011. In fact, he later learned that his decision to conceal his age may have worked in his favor.
He recalled a conversation with showrunner Steven Peterman, who told him the production might have reconsidered casting him had they known the truth during the pilot stage.
The age gap between Earles and his character — and much of the cast — was notable. Cyrus was just 13 when the show began, while her co-stars Emily Osment and Mitchel Musso were in their early teens, and Moisés Arias was even younger. Meanwhile, Cyrus’ real-life father, Billy Ray Cyrus, played their on-screen dad.
Lieblein noted on the podcast that Earles’ presence ultimately helped shape the show’s dynamic. Though he was an adult off-camera, his youthful look allowed him to blend seamlessly with the younger cast — something that contributed to the series’ success.
The story has since resurfaced online, drawing widespread attention and amusement from fans who continue to marvel at how convincingly Earles pulled off playing a teenager well into adulthood.
Hannah Montana premiered in 2006 and became a defining pop culture staple of the era, launching Cyrus into global stardom. For viewers, Jackson Stewart was always the goofy older brother — even if, behind the scenes, he was much older than anyone realized.
