Jason Earles is experiencing deja vu. After first watching his Hannah Montana costar Miley Cyrus skyrocket to pop star fame in the late 2000s, he’s now witnessed a second Disney Channel leading lady — Olivia Rodrigo — do the exact same thing in the early 2020s.
And in a recent interview with People, the 45-year-old actor opened up about what it’s been like to be a part of someone else’s massive career transformation two times over. “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 told the publication. “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,” he continued. “It happened so quickly. 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.”
After wrapping up Hannah Montana — on which he played Cyrus’ brother Jackson — in 2011, Earles would continue on to join the crew of High School Musical: The Musical: The Series, which gave Rodrigo her big break playing Nini Salazar-Roberts. He signed on as an acting coach for the Disney + series’ young stars and has now joined the cast for its upcoming third season.
“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,” he said of his time working on the show, a spinoff of Disney’s High School Musical films. “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.”
While Rodrigo’s role on Disney’s Bizaardvark was her initial stepping stone to success, it was her role on HSMTMTS that established her as a young singer-songwriter to watch. A song she wrote and sang for the show, “All I Want,” charted on the Billboard Hot 100 and kickstarted the international fame she went on to solidify with No. 1 singles “Drivers License” and “Good 4 U” and her Grammy-winning debut album Sour.
Meanwhile, Cyrus almost instantly became an idol for young girls across the planet by playing Miley Stewart/Hannah Montana on Disney Channel. A portion of her 53 Billboard Hot 100 charting songs were released through the show, including “The Climb,” “He Could Be The One” and “Nobody’s Perfect.”
“She’s so funny and so talented,” Earles told People of his former onscreen sister. “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.”