Key moments
Jason Earles, best known for his portrayal of Jackson Stewart on the iconic Disney Channel series Hannah Montana, has remained a significant figure in the show’s legacy. As fans celebrate the 20th anniversary of the series, which first aired in 2006 and concluded in 2011, Earles’ contributions and reflections on the show have come to the forefront.
The Hannah Montana 20th anniversary special was released on March 24, 2026, marking two decades since the show first captivated audiences. Earles, now 48 years old, has been actively engaging with fans through a Hannah Montana-themed podcast, where he shares anecdotes and insights from his time on the show.
In a recent interview, Earles recounted a humorous moment when Disney executives advised him to delay starting a family due to his age at the time of casting. “I was like, ‘No kids.’ He’s like, ‘Let’s go ahead and keep it that way for a few years,’” he recalled, illustrating the unique circumstances surrounding his early career.
While Earles has embraced his role in the series, not all cast members have participated in the anniversary celebrations. Notably, Emily Osment, who played Lily Truscott, did not attend the reunion. At 34 years old, Osment has expressed her gratitude for the impact Hannah Montana had on her life, stating, “Hannah Montana changed my life, it gave me a lifelong respect for this medium of comedy, it taught me discipline, patience, timing and respect working in an adult space so young.”
Miley Cyrus, who starred as Miley Stewart/Hannah Montana, has also reflected on her time in the series, emphasizing her desire to preserve the essence of the show. “I didn’t want to do this modern approach to Hannah. I wanted to keep it preserved,” she stated, highlighting the show’s lasting significance in her career.
The enduring popularity of Hannah Montana has solidified its status as a pop culture pillar, with fans reminiscing about the show’s themes of family, friendship, and the challenges of adolescence. As the anniversary approaches, many are looking back at the show’s influence on their lives and the careers of its stars.
As reactions to the anniversary special continue to pour in, fans and former cast members alike are expressing their appreciation for the series that shaped a generation. Jason Earles’ ongoing involvement through his podcast and public appearances serves as a reminder of the lasting impact Hannah Montana has had on its audience and the entertainment industry.