'Hannah Montana' 's Jason Earles on Mentoring the Next Generation of Disney Stars: 'It's Wild'

"It's just fascinating to see in the front row as it goes down," the Hannah Montana alum tells PEOPLE about watching the High School Musical: The Musical: The Series cast rise to fame

Photo: Anne Marie Fox/Disney

Jason Earles is still getting the best of both worlds.

More than 11 years after starring on Hannah Montana, the actor returns to his Disney roots in High School Musical: The Musical: The Series season 3.

Speaking with PEOPLE, the Disney Channel alum talks about how his role in the upcoming season came about and what it's been like working alongside the show's talented group of stars, including Olivia Rodrigo, Joshua Bassett, Sofia Wylie and Matt Cornett.

Though Earles plays a new character named Dewey, a counselor at Camp Shallow Lake where the students are spending their summer, he has actually been working on the Disney+ series as an acting coach since season 1.

He explains that before the show started filming, he was approached by the former Disney Channel casting head Judy Taylor about working behind the scenes with the cast as "an in-house camp counselor, den mother and mentor."

"They really were worried about making sure the kids had a very safe environment to be young performers [and] have all the resources that they need for their mental health and their professional development," explains Earles, 45. "I was thrilled to be able to provide that for the kids going into it as they started. That was the genesis of it. Then, I just loved them all so much that I just keep coming back."

Jason Earles High School Musical The Musical The Series
Jason Earles/Instagram

This season is especially fun for Disney fans as Earles also shares the screen with High School Musical alum Corbin Bleu, with whom he previously worked on the pilot of Hannah Montana.

"As the two elder statesmen on the set, we're observing this new cast and just seeing how incredibly talented they are," Earles says. "[Corbin] jumped right in the role of being a mentor for the kids, wanting to be somebody that they could come to and ask advice."

Despite Bleu playing himself on the show and Earles playing a different character, the actor clarifies that Hannah Montana does exist in the show's universe — and fans can anticipate a handful of meta references about "the absurdity of the whole situation" throughout the season.

"The first season people were, 'Oh my God, this is crazy meta.' Season 3 is 10 times that," he says. "It's just really, really out there. Season 2, for me, was a little more serious. I love the fact that in season 3 we've gotten back to more of the fun. It feels a little bit more High School Musical and a little less Dawson's Creek."

Having been a part of the show since the very beginning, Earles admits it's been "wild" watching a whole new set of Disney stars rise to stardom firsthand. He even notes that Olivia Rodrigo's recent music success has reminded him a lot of Miley Cyrus's early career.

Miley Cyrus, Olivia Rodrigo
Kevin Mazur/WireImage, Harry Durrant/Getty

"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," he says. "The show premiered, we told them, 'She's a pop star,' [and] suddenly, she was a pop star."

"And then Olivia Rodrigo when 'drivers license' dropped, the world just decided that she was the biggest pop star on the planet. It happened so quickly," he continues. "It was so shockingly similar to Miley's rise that I was like, 'How can I possibly be this close to this twice in one lifetime?' It's just fascinating to see in the front row as it goes down."

While Earles has become well-known for his role as Jackson on Hannah Montana, he never imagined the show would amount to the success it did when it first premiered in 2006.

"I actually thought I was going to single-handedly ruin the show because when we did the pilot, Jackson originally was really introverted, and he didn't know how to deal with his sister's success at all," he explains. "I had an orangutan hand puppet that I talked with. The concept was so dumb, and it made the show so childish that I don't think anybody would've watched the show. Then we ended up cutting it two days before we shot the pilot and it ended up being the Jackson that you came to know."

HANNAH MONTANA - "Been Here All Along" - Disney Channel's "Hannah Montana" honors military families with a touching episode that includes cameo appearances by real families of the armed services and two new Hannah Montana songs: the heartfelt ballad "Been Here All Along" and the upbeat "I'm Still Good," a performance interspersed with greetings from military families to their deployed loved ones. The "Hannah Montana Forever Family Salute" premieres SUNDAY, AUGUST 22 (8:00-8:30 p.m., ET/PT). 40 special messages from military families will air throughout the evening (8:00-9:30 p.m., ET/PT) and will be available with the episode at DisneyChannel.com/Salute.
Eric McCandless/Disney Channel via Getty

He also contributes Cyrus's role on the show as a big reason why it took off.

"She's so funny and so talented," he says of his former costar. "She was the perfect blend of somebody who was really pretty and could have decided she wanted to be perfect all the time but she was so silly and didn't take herself so seriously that she couldn't be the butt of the joke. She was so relatable. It really felt like, when you watch her, [you] could be best friends with her. She seems like she'd be a lot of fun. And she was. And is."

Even after all these years, Earles says "it's really humbling" to have been a part of something as big as Hannah Montana and witness the impact it had on so many people. "To run into adults now who say that it had such an impact on a big chunk of their childhood, it's so much bigger and so much better received than I thought it ever had a chance of being," he says.

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Season 3 of High School Musical: The Musical: The Series premieres Wednesday on Disney+.

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