Jason Earles is reflecting on his past days as Jackson Stewart on the hit Disney TV show “Hannah Montana.” While celebrating the show’s 20th anniversary in late March 2026, the Disney alum revealed what he would tell his younger self while filming the series in the early 2000s.
What Would Jason Earles Tell His Younger Self While Filming ‘Hannah Montana’ In 2006?
On March 23, 2026, the cast of “Hannah Montana” gathered at the El Capitan Theatre in Los Angeles, California, to celebrate the show’s 20th anniversary.
While speaking with PEOPLE, Earles, 48, reflected on his early days filming the series alongside Miley Cyrus.
“I think just… settle in sooner,” Earles said, adding that he was concerned he was not the right fit for the series when production began.
“I was really nervous about fitting in and if my humor was the right sense of humor for the show and if I was… approaching it as an actor the right way,” he said. “I think I was just not as confident as early as I could have been.”
Earles Was Nervous About Filming ‘Hannah Montana’ For A Bigger Reason
Earles was not only worried about his on-set skills, according to The Blast. During an episode of his podcast, “Best of Both Our Worlds,” the actor revealed he was concerned he would be fired from the series due to a secret he was holding on to.
“I was desperately afraid that I was going to be fired and recast because I had a big secret,” he said before admitting he lied to producers about his age during the audition.
“When I auditioned for the show, I lied to them and told them I was 18 years old,” he revealed, despite actually being 28.
Earles And Other ‘Hannah Montana’ Alum Gather On The Red Carpet For The Show’s Disney+ Special
Earles is not the only “Hannah Montana” alum reflecting on their time on the show. According to a previous report from The Blast, Cyrus sat down with the host of the “Call Her Daddy” podcast, Alex Cooper, to talk about the show’s impact on pop culture during a Disney+ special.
“Hannah Montana will always be a part of who I am. What started as a TV show became a shared experience that shaped my life and the lives of so many fans, and I’ll always be thankful for that connection,” Cyrus said about the TV show. “The fact that it still means so much to people all these years later is something I’m very proud of. This ‘Hannahversary’ is my way of celebrating and thanking the fans who’ve stood by me for 20 years.”
Actor Shanica Knowles, who played one of the show’s mean girls, also shared a moving message as she looked back on the series, calling it “a wild ride.”
In her message, Knowles spilled the tea on what it was like to work with Cyrus, calling the “Flowers” singer one of the most “down-to-earth home girls” she has ever worked with, and then mentioned some of their childhood experiences.
“The world may see you as Miley Cyrus, but I’ll always see you as the girl I had fun slumber parties with, wrote songs together with, talked about boys together with, and stayed up all night laughing on the phone with. I’ll always see you as just…Miley,” Knowles wrote.
Emily Osment Says The Disney Show ‘Changed My Life’
While the “Hannah Montana: 20th Anniversary Special” premeire included a handful of the show’s main cast, Cyrus’ on-screen besties, Emily Osment and Mitchel Musso, were notably absent.
On Instagram, Osment said her absence was due to her work on the CBS show “Georgie & Mandy’s First Marriage.”
The actress also shared an emotional message in her caption, saying that working on “Hannah Montana” not only “changed my life” but also gave the performer “a lifelong respect for this medium of comedy.”
Osment went on to say that she is always moved when meeting “HM” fans over the years, adding that the “sweet messages” mean more to her than people know.
“Thank you for letting me into your living rooms and I hope to still be there many years from now. Would never be where I am without you guys,” she finished.
Musso Thanks The Fans For Sticking With Him Over The Years
Musso, meanwhile, reflected on the show with a carousel of his own images. In the caption, the “Hey” singer said the show would forever be “wrapped around my heart,” before thanking the audience for sticking by his side over the years.
“Thank you for believing in a goofy kid from Texas who wore some questionable outfits with a haircut like that,” he wrote. “To all of you, thank you for welcoming me into your homes and hearts 20 years ago and still allowing me to be here today. I’m honored we get to share all of this together.”
