In a heartfelt reflection, Jason Earles recently celebrated the 20th anniversary of the beloved Disney Channel series Hannah Montana, which first aired in 2006. Earles, who played the iconic character Jackson Stewart, shared his thoughts on the show that not only entertained millions but also shaped his career and life.
The Hannah Montana 20th anniversary special was released on March 24, 2026, marking two decades since fans were first introduced to Miley Stewart, played by Miley Cyrus. The show, which ran until 2011, became a pop culture phenomenon, leaving a lasting legacy in the hearts of its viewers.
Reflecting on his journey, Earles recalled how he was asked by Disney executives to wait a few years before starting a family after he had initially lied about his age to land the role. “I was like, ‘No kids.’ He’s like, ‘Let’s go ahead and keep it that way for a few years,’” he said, highlighting the unique circumstances of his early career.
While many cast members reunited for the anniversary, not everyone was present. Notably, Emily Osment, who played Lilly Truscott, did not attend the reunion. At 34 years old, Osment expressed her gratitude for the show, 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.” Her words resonate with many who grew up watching the series.
As the anniversary approached, Earles also took to hosting a Hannah Montana-themed podcast, further connecting with fans and reminiscing about the show’s impact. The podcast serves as a platform for him to share behind-the-scenes stories and engage with the community that has supported him over the years.
In a touching moment, Osment expressed her appreciation for the fans, saying, “I wanted to say hello and thank you to everybody that has stuck by us for all these years.” This sentiment reflects the deep bond that the cast shares with their audience, a relationship that has endured through the years.
Meanwhile, Miley Cyrus, who has evolved significantly since her days on the show, expressed her desire to preserve the essence of Hannah Montana. “I didn’t want to do this modern approach to Hannah. I wanted to keep it preserved,” she stated, emphasizing the importance of the show’s original charm and its place in pop culture history.
As the community celebrates this milestone, the legacy of Hannah Montana continues to thrive, reminding fans of the joy and laughter it brought into their lives. Jason Earles, now 48 years old, remains a cherished figure in this narrative, embodying the spirit of a show that changed the landscape of children’s television.
