Jason Earles Shares His 'All-Time Favorite, Most Honest' “Hannah Montana” Moment with Miley Cyrus That He Improvised
Jason Earles Shares His 'All-Time Favorite, Most Honest' “Hannah Montana” Moment with Miley Cyrus That He Improvised
Tereza ShkurtajSat, March 28, 2026 at 6:00 PM UTC
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Jason Earles.Credit: Amy Sussman/Getty -
On March 23, Jason Earles made an appearance at the Hannah Montana 20th Anniversary special premiere in Los Angeles
During the event, the 48-year-old actor recalled his "favorite hijinks" moment from the franchise's history, saying it took place in 2009's Hannah Montana: The Movie
He explained why it fit so perfectly during his on-screen sister Miley Stewart’s (Miley Cyrus) emotional reveal scene
For many fans, Hannah Montana remains one of Disney Channel’s most beloved sitcoms, thanks in large part to its humor and heartfelt family dynamic.
At the center of that dynamic was Jason Earles as Jackson Stewart, the goofy yet fiercely loyal older brother to Miley Stewart. His onscreen chemistry with "little sister" Miley Cyrus helped define the show’s charm, capturing the chaos and care of a real sibling relationship.
Reflecting on the series during a recent conversation with Entertainment Weekly, Earles looked back on a standout memory that perfectly summed up Jackson’s personality. “My favorite hijinks is actually in the movie,” the 48-year-old actor told the outlet, referring to the 2009 film, Hannah Montana: The Movie.
Jason Earles in 'Hannah Montana: The Movie.'Credit: Disney
That special moment came in the film when Miley performs “You'll Always Find Your Way Back Home” for a large hometown crowd after revealing her secret identity as Hannah Montana — an emotional scene centered around her connection to her fans and roots.
As Earles explained, “There's an improv moment at the end after the whole, like, secret reveal, and then she takes the secret back, and she's driving by on the truck, and they pan across the audience, and I just throw the big loser sign at her.”
The playful jab captured everything fans loved about Jackson — his ability to undercut serious moments with humor while still showing unwavering support for his sister. Throughout the show’s four-season run, Jackson and Miley constantly got on each other’s nerves in classic sibling fashion.
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Yet underneath all the teasing was a deep bond, with both characters repeatedly proving they would do anything for each other. Their shared sense of humor became a cornerstone of that relationship, making the improvised “loser sign” feel especially authentic.
“That's, like, my all-time favorite, most honest ‘Jackson moment’ for the whole run,” Earles told Entertainment Weekly.
Jason Earles and Miley Cyrus on 'Hannah Montana.'Credit: Eric McCandless/Disney Channel via Getty
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This year, Hannah Montana celebrated its 20th anniversary with a special, which premiered on Tuesday, March 24 — exactly two decades after the original 2006 debut.
The special featured rare behind-the-scenes footage, recreated sets, and performances of classic songs alongside a new track from Cyrus. Cast members including Moises Arias, Cody Linley, and Ashley Maria Perez de Tangle attended the premiere, while Emily Osment and Mitchel Musso were notably absent.
The Hannah Montana 20th Anniversary Special is available to stream on Disney+ and Hulu.
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Source: “AOL Entertainment”
