Old School Americana & Nostalgia


What Happened to Jason Earles? What Jackson From ‘Hannah Montana’ is Doing Now

What Happened to Jason Earles? What Jackson From ‘Hannah Montana’ is Doing Now

For four seasons, Jason Earles had a front-row seat to watch Miley Cyrus star in Hannah Montana as her brother, Jackson Stewart. Earles did have some experience in the sitcom world before landing on the Disney Channel series. Since it’s been a stretch from starring on Hannah Montana, what in the world has Earles been doing? Let’s take a look and see.

But we will start our journey with a little backtracking here. Earles appeared in the CBS sitcom Still Standing along with National Treasure in 2004. Then came his turn on Hannah Montana, where Earles got his fair share of laughs on there. Watching the way that Earles interacted with Cyrus, some people might think that they are related.

Earles was asked about that very thing during part of an interview for WIRED‘s AutocompleteInterview a few years ago. “I will say that even though I’m not genetically related to the Cyruses, Billy Ray, like, almost immediately adopted me as an official Cyrus and was calling me Jason Ray Cyrus,” Earles said.

‘Hannah Montana’ Star Jason Earles Befriends Cyruses

“They had a spare room made up for me in their house so if I didn’t want to drive back and forth, I would crash at their place. They were exceptionally wonderful and gracious, so I do consider Miley to be like family and really like a little sister, but we do not share any genetics at all.”

At the start of his time on Hannah Montana, Earles was 29 years old…but he was playing a 16-year-old. Go figure.

Well, after Hannah Montana closed up shop, Earles got a part on another Disney Channel show titled Phil of the Future. On there, he played Grady Spaggett. Earles and some other Hannah Montana cast members also popped up on the Disney Channel Games in 2007 and 2008.

During the third and fourth seasons of High School Musical: The Musical: The Series, Earles scored cameo appearances. Earles also was an acting coach on there since the show’s first season.

He talked with People about being on the show and working with the cast.

“I was thrilled to be able to provide that for the kids going into it as they started. That was the genesis of it,” Earles said. “Then, I just loved them all so much that I just keep coming back.”

Actor Compares Olivia Rodrigo, Miley Cyrus Situations

Earles also pointed out a comparison between lead star Olivia Rodrigo, who had a big hit song and seven Grammy nominations, and Hannah Montana lead star Miley Cyrus.

“For me, what has been mind-blowing is I was there during Hannah Montana, and I watched Miley turn into the biggest pop star in the world overnight,” Earles said. “The show premiered, we told them, ‘She’s a pop star,’ [and] suddenly, she was a pop star.”

That’s quite interesting to note. Yet some Hannah Montana fans might be interested in seeing a reboot of the Disney Channel show. Could it happen? Earles talked about it in an interview with E! Online in 2022. “A Hannah spin-off, sequel, or reimagining makes a lot of sense,” Earles said. “I think the right people would have to be involved.” That would include Miley Cyrus in some way.

Earles married his longtime girlfriend Katie Drysen in August 2017. At this time, they do not have any children.