Jason Earles

Jason Daniel Earles is an American actor, comedian, director, and acting coach. He is best known for playing Jackson Stewart, the lovable older brother, on the Disney Channel series Hannah Montana, and Rudy Gillespie, the sensei, on the Disney XD show Kickin' It. Earles started acting at age three and built a career in theatre before transitioning to screen. His comedic timing and everyman charm made him a fixture of 2000s Disney Channel programming. Today, he continues to act, directs multi-camera sitcoms, and hosts a podcast celebrating the 20th anniversary of Hannah Montana. Fans remember him as the goofy big brother who brought warmth and humor to millions of households. [edit]

Earles was born in San Diego, California, and moved around as a child, living in Ohio and Washington state before his family settled in Oregon. He graduated from Glencoe High School in Hillsboro. His love for performing started early: at age three, he played Hansel in a stage production of Hansel and Gretel. In high school and college, he dove into theatre, earning four KC/ACTF Irene Ryan nominations for his work at Rocky Mountain College in Billings, Montana. After graduating with a BA in theatre arts in 2000, he moved to Los Angeles to pursue acting. His first television credit was a sketch on MADtv in 2003, and he made his film debut in 2004 as Thomas Gates in National Treasure. In 2005, he appeared in American Pie Presents: Band Camp as Ernie Kaplowitz. [edit]

Earles landed his breakthrough role in 2006 when he was cast as Jackson Stewart on Disney Channel's Hannah Montana. The show ran for 98 episodes and turned him into a household name. Interestingly, he was 28 when the show began, playing a 16-year-old character; producers did not realize his real age for the first eight episodes. During the show's run, he won a Teen Choice Award in 2009 for Hannah Montana: The Movie. After the series ended in 2011, he starred as Rudy Gillespie in the Disney XD martial arts comedy Kickin' It for 84 episodes. In 2013, he voiced Santa in the web series The Most Popular Girls in School. More recently, he played Dewey Wood in seasons 3 and 4 of High School Musical: The Musical: The Series on Disney+. He has also worked as a director on multi-camera sitcoms. As of 2026, he hosts the podcast Best of Both Our Worlds: The Official, Unofficial Hannah Montana Podcast and has upcoming film projects Second Chances and Worst Man. [edit]

Earles is widely recognized for his comedic timing and the role of Jackson Stewart, the lovable, goofy older brother. Media portrays him as a nostalgic figure for millennial and Gen Z audiences who grew up on Disney Channel. He engages with fans through his podcast and social media, maintaining a lighthearted, self-aware tone. His social media voice is playful and appreciative of the fan community. Audiences connect with his genuine, down-to-earth personality and the warmth he brought to his Disney roles. [edit]

The cultural footprint of Jason Earles remains anchored in the enduring legacy of Hannah Montana, where he is revered not merely as an actor but as the beloved brother who defined a generation of Disney nostalgia. Within the decentralized community that surrounds the franchise, Earles operates under the informal moniker "Duke of Earles," a title derived from his social media handle that has become a touchstone for fans celebrating the show's 20th anniversary. This fanbase, largely subsumed under the broader Hannah Montana audience, has demonstrated significant influence by driving high-profile reunion events, including the April 2026 premiere of the Hannah Montana 20th Anniversary Special. Their collective demand also catalyzed the launch of Best of Both Our Worlds: The Official, Unofficial Hannah Montana Podcast in March 2026, a project designed to satisfy the appetite for behind-the-scenes narratives and reunion content.

iFANN has evaluated this profile within its Global Fame Engine, yet the data indicates that Jason Earles does not currently hold a placement in the published rankings, standing as EVALUATED_UNRANKED without a specific global or topical score. While the actor maintains a proactive presence through Cameo messages and digital engagement, the absence of a formal ranking reflects a status where his fame is deeply nostalgic rather than currently dominant in global metrics. The narrative surrounding his career is further enriched by verified lore regarding his casting, specifically the widely retold story that he claimed to be 18 when he was actually 28 to secure the role, a deception that reportedly surprised co-star John Cena and led to executive concerns about family dynamics during production.

This physical comedy lore extends to accounts of the toll the slapstick took on his body, adding a layer of professional respect to his persona. Though the fanbase lacks a single official name beyond the franchise umbrella, their devotion ensures that Earles remains a central figure in the celebration of 2000s pop culture, bridging the gap between the original broadcast era and modern retrospectives.[edit]

Jason Earles holds a blue belt in Brazilian jiu-jitsu and is an avid video game player with a particular focus on Destiny. A devoted supporter of the Cleveland Browns, he maintains his allegiance despite the team's historical struggles. In a notable production shift, the original concept for Jackson Stewart involved a hand puppet, but the prop was scrapped three days before shooting the pilot when a scene without it proved more effective. Earles frequently embedded subtle references into episodes, such as a Back to the Future guitar riff in the episode She's a Super Sneak. He has shared the screen with a diverse array of talent including Larry David, Brooke Shields, Dolly Parton, James Spader, Michael Chiklis, and Nicolas Cage.

A widely retold story from the 20th anniversary era details how Earles admitted to lying about being 18 when he was actually 28 to secure the role, a confession that became a central piece of fan folklore regarding his casting. Another anecdote involves co-star John Cena expressing shock upon learning Earles was 33 years old during their interactions, cementing the narrative of his successful physical deception. Fans also recall his favorite on-set memory involving the cheese jerky song, a musical number cited as a quintessential example of the series' absurd humor. Retrospective interviews confirm that the extensive physical comedy required for the character often took a genuine toll on his body, transforming his legacy from simple comic relief to one of endurance.[edit]

Earles married his first wife, Jennifer, in 2002; they divorced in 2013. He married Katie Drysen on August 13, 2017. The couple lives in Toluca Lake, California, with their two cats, Donut and Zeke. No children are publicly reported from either marriage. Earles has not shared details about his parents or siblings publicly. [edit]

Earles is closely associated with his Hannah Montana co-stars Miley Cyrus, Billy Ray Cyrus, Emily Osment, Mitchel Musso, and Moisés Arias. On Kickin' It, he worked with Leo Howard and Olivia Holt. He also shared the screen with Nicolas Cage in National Treasure and Dolly Parton on Hannah Montana. More recently, he acted alongside Joshua Bassett on High School Musical: The Musical: The Series. [edit]

Earles married his first wife, Jennifer, in 2002, before his Hannah Montana fame. The marriage ended in divorce in 2013. No details about the split or any children from that relationship have been made public. On August 13, 2017, he married Katie Drysen. The couple lives in Toluca Lake, California, with their two cats. As of 2026, Earles remains married to Drysen, and no children have been reported from either marriage. [edit]

Updated for 2026, research by the iFANN Editorial Team places Jason Earles' net worth at $2 Million. His financial standing stems primarily from acting salaries accrued during his long-running roles on Hannah Montana and Kickin' It, alongside directing fees for multi-camera sitcoms. Additional revenue streams include earnings from his podcast Best of Both Our Worlds and residuals generated through syndication and streaming of his Disney productions. No major endorsements, business ventures, or real estate holdings are publicly documented. His wealth has accumulated steadily through his acting career, though he has not pursued high-profile commercial deals.[edit]

Earles won a Teen Choice Award in 2009 for his performance in Hannah Montana: The Movie. He also received four KC/ACTF Irene Ryan nominations for his collegiate theatre work but did not win. [edit]