Behind the Scenes with Jackson Stewart: Hannah Montana’s Brother

Jackson Stewart, “Hannah Montana”

When it comes to iconic family sitcoms, “Hannah Montana” holds a special place in the hearts of many.

The show not only catapulted Miley Cyrus to stardom but also introduced us to an unforgettable character, her on-screen brother, Jackson Stewart.

Portrayed by Jason Earles, Jackson’s quirky antics and brotherly moments were pivotal to the show’s success.

jason earles hannah montana
Jason Earles “Hannah Montana”
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Who is Jason Earles?

Jason Earles, born on April 26, 1977, took on the role of Jackson Stewart, the older brother of Miley Stewart, played by Miley Cyrus in the iconic TV show Hannah Montana.

Despite being nearly 30 when the show began, Earles convincingly played the teenage Jackson, who was 16 at the start of the series.

His character was known for his comedic timing, love for video games, and the typical brother-sister banter that added a layer of relatability to the show.

Jason Earles


Jackson Stewart’s character was essential in balancing the surreal aspects of Hannah Montana’s double life with the normalcy of teenage struggles.

He grounded the show with his down-to-earth personality and represented the average American teenager, despite the extraordinary circumstances of his family.

His role highlighted the importance of family support and the everyday challenges of growing up.

What happened to Jason Earles after the show ended?

After “Hannah Montana” ended, Jason Earles continued to pursue his acting career. He took on various roles, including:

  • Flynt Rogers in Brat TV’s “Hotel Du Loone” in 2018.
  • A character named Angel in Pure Flix’s “Mood Swings” in 2019.
  • The role of Dewey Wood, a camp director in the Disney+ series “High School Musical: The Musical: The Series” in 2022.

Additionally, he has an upcoming role as Taco Tom in a film titled “Second Chances,” set to be released in 2023.

Earles has also been involved behind the scenes, teaching acting classes to children in New York in 2011. His dedication to the craft extends beyond the screen, serving as a great example and mentor for aspiring actors.

Jason Earles
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On a personal note, Jason Earles married Katie Drysen in 2017, and they remain married. He tends to keep his family life private, focusing on his career and occasionally hinting at the possibility of a “Hannah Montana” spinoff in the future.

It’s clear that Earles has been quite active in the entertainment industry since his days on the popular Disney show.

Jason Earles’ Diverse Portfolio of Proffesional Projects

Jason Earles has been quite active in the entertainment industry, both in front of and behind the camera. Here are some of his notable involvements:

  • Acting: After “Hannah Montana,” Earles continued acting, notably as Rudy Gillespie in the Disney XD series “Kickin’ It,” which aired from 2011 to 2015. He also appeared in various films such as “Hunted” and “Battle Drone,” showcasing his versatility as an actor.
  • Voice Work: He has done extensive voice-over work, including for the popular web series “The Most Popular Girls in School”.
  • Directing: Earles has added director to his list of talents, directing multi-camera sitcoms in recent years.
  • Teaching: He served as an acting coach for “High School Musical: The Musical: The Series” and guest-starred in the show as Dewey Wood, a camp counselor.
jason earles high school musical
Jason Earles “high school musical”
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His diverse range of projects reflects his dedication to the craft and his ability to adapt to various roles within the industry.

Earles continues to contribute to the world of entertainment, influencing new generations of actors and creators.

How has Jason Earles Evolved as an Artist over time?

Jason Earles’ evolution as an artist over time reflects a journey of versatility and growth.

Starting with his role as Jackson Stewart in “Hannah Montana,” Earles has expanded his repertoire to include a variety of characters and projects.

Here’s a look at his artistic evolution:

Versatility in Roles: From playing a teenager on “Hannah Montana” to a martial arts instructor in “Kickin’ It,” Earles has shown a wide range in his acting abilities. He has taken on roles that challenge him and allow him to explore different facets of his talent.

Voice Acting: Earles has lent his voice to several animated characters, demonstrating his skill in bringing to life characters through voice alone.

Martial Arts: Not just an actor, Earles is also a skilled martial artist, which has influenced his roles and allowed him to perform his own stunts in action-oriented projects.

Directing and Teaching: Moving behind the camera, Earles has ventured into directing, further expanding his understanding of the creative process. He has also shared his experience by teaching acting, influencing the next generation of performers.

Jackson Stewart Hannah Montana
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Continuous Learning: Earles’ involvement in various aspects of entertainment, from acting to directing, shows his commitment to learning and adapting within the industry.

Overall, Jason Earles has evolved from being known primarily for a single role to becoming a multifaceted artist with a diverse set of skills and experiences.


Jackson Stewart, as portrayed by Jason Earles, was more than just Hannah Montana’s brother; he was a symbol of adolescence, family, and the comedic relief that made the show a hit.

Moreover, his character left an indelible mark on pop culture, reminding us of the importance of laughter and the enduring bond of family.

Furthermore, in revisiting the legacy of “Hannah Montana,” we celebrate not only the titular character but also the supporting roles that made the series unforgettable.

Jackson Stewart, with his humor and heart, will always be a cherished part of the Stewart family story.




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