If you spent any time near a TV in the mid-2000s, you know Jason Earles as Jackson Stewart, the goofy, snack-obsessed older brother of Miley Stewart in Hannah Montana. The reason he's a viral sensation every few years is the "Age Reveal." When the show started in 2006, he was 29 years old playing a 16-year-old. Today, in 2026, he’s 48 and honestly looks like he could still pass for a grad student.

But for our kids, he’s transitioned from "funny brother" to "cool mentor." In the last few years, he’s been working as an acting coach and producer for Disney+ projects. He was a series regular and a mentor to the cast of High School Musical: The Musical: The Series, helping stars like Olivia Rodrigo and Joshua Bassett navigate the "Disney Machine."

When your kids see him trending on TikTok or YouTube, it's usually because of a "then vs. now" edit or a clip of him doing insane physical stunts that he’s still pulling off in his late 40s.

There’s a specific brand of "Disney Channel Humor" that Jason Earles basically pioneered. It’s loud, it’s physical, and it’s centered on the idea that being the "uncool" person is actually the coolest way to be.

If your kid is asking about "that guy from the memes," here are the shows that actually hold up.

Ages 7+ It’s the classic. While the "secret identity" plot is the hook, the B-plots involving Jason Earles and Billy Ray Cyrus are often the funniest parts for parents. It’s safe, it’s clean, and it’s a time capsule of 2006 fashion (for better or worse). Check out our full guide to Hannah Montana

Ages 6-11 This is the "boy-centric" answer to the Disney sitcom formula. It’s focused on a group of misfits at a karate dojo. Earles plays the adult mentor who is often more immature than the kids. It’s great for kids who like Cobra Kai but aren't ready for the teen drama and violence of that show.

Ages 10+ Earles joined the cast in later seasons as a camp director. This show is much more "meta" and modern. It deals with theater kid culture, LGBTQ+ relationships, and the pressures of social media. It’s a step up in maturity from his earlier work.

Jason Earles is one of the few Disney stars who seems to have come out the other side of the "child star" factory completely intact and healthy. He’s often spoken about the pressures young actors face, which makes him a great entry point for a conversation with your kids about digital fame.

If your kid is obsessed with becoming a YouTuber or a TikTok star, Earles' career is a good example of "longevity through craft." He didn't just stay famous for being a face; he learned how to produce, how to coach, and how to stay relevant by helping others.

Learn more about helping kids handle the pressure of social media fame

Parents often worry that mid-2000s sitcoms are just "loud noise and bright colors." While Hannah Montana definitely has its "laugh track" moments, the performances—especially Earles' physical comedy—are actually quite skilled. It’s not educational in the "math and science" sense, but it’s high-quality entertainment that doesn't rely on the mean-spiritedness found in some modern "influencer" content.

Since the 20th Anniversary Special is the reason he's trending, use it as a "bridge" moment.

Q: How old was Jason Earles in Hannah Montana? Jason Earles was 29 years old when the show started in 2006 and 34 when it ended. He was playing a character who started the series at age 16, which has become a legendary "fun fact" in pop culture.

Q: Is Jason Earles in the new Hannah Montana special? Yes, Jason Earles is a confirmed lead for the 20th Anniversary Special on Disney+, appearing alongside Miley Cyrus and the rest of the original cast to celebrate the show's legacy.

Q: What is Jason Earles doing now in 2026? As of 2026, Jason Earles is primarily working as an acting coach and mentor for young Disney talent, while also appearing in "legacy" roles and producing behind-the-scenes content for Disney+.

Q: Is the show Kickin' It appropriate for a 7-year-old? Yes, Kickin' It is very appropriate for 7-year-olds; it features slapstick comedy and "cartoonish" martial arts action with positive themes about teamwork and perseverance.

Jason Earles is trending because he’s a rare constant in the ever-changing world of kid’s media. Whether he’s the goofy brother from your childhood or the mentor in your kid’s favorite show, he represents a "safe" side of the internet and TV.

If your kids are diving into the Hannah Montana archives this month, don't fight it. It's a chance to share a bit of your own pop-culture history with them—just be prepared to explain why everyone was wearing three layered tank tops and low-rise jeans in 2006.