“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 explained. Earles played Miley's brother "Jackson" on the Disney Channel series. “The show premiered, we told them, ‘She’s a pop star,’ [and] suddenly, she was a pop star.”
He continued, “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. 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.”
Now, Earles plays an acting coach on High School Musical: The Musical: The Series — in which the "good 4 u" singer was a series regular before dropping her chart-topping debut album Sour. Back in May, it was announced that Rodrigo would instead be returning for the third season of the Disney+ series as a recurring guest.