Key moments
Jason Earles, best known for his role as Jackson Stewart on the iconic Disney Channel series Hannah Montana, is in the spotlight as the show celebrates its 20th anniversary. The series, which originally aired from 2006 to 2011, has left an indelible mark on pop culture, and Earles’ contributions to the show continue to resonate with fans.
On March 24, 2026, the Hannah Montana 20th anniversary special was released, rekindling nostalgia for a generation that grew up with the show. Earles, now 48 years old, has embraced his role in the series and remains connected to its legacy through various projects, including hosting a Hannah Montana-themed podcast. This platform allows him to engage with fans and share behind-the-scenes stories from the show.
Reflecting on his time on the show, Earles shared a humorous anecdote about his early days in the industry. He recounted how Disney executives advised him to wait a few years before starting a family after he had lied about his age to secure his role. “I was like, ‘No kids.’ He’s like, ‘Let’s go ahead and keep it that way for a few years,’” he recalled, highlighting the unique challenges young actors face in Hollywood.
While Earles has remained a prominent figure in the Hannah Montana universe, not all original cast members participated in the anniversary celebrations. Notably, Emily Osment, who played Lilly Truscott, did not attend the reunion. At 34 years old, Osment has expressed her gratitude for the opportunities the show provided her, 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 the titular character, also shared her thoughts on the show’s legacy. She expressed a desire to preserve the original essence of Hannah Montana, stating, “I didn’t want to do this modern approach to Hannah. I wanted to keep it preserved.” This sentiment resonates with many fans who cherish the show’s original charm.
The impact of Hannah Montana extends beyond its original run, as it continues to influence new generations of viewers. The show’s blend of humor, music, and relatable themes has solidified its status as a beloved classic. As the 20th anniversary unfolds, fans are reminded of the laughter and lessons the series imparted.
As the celebrations continue, reactions from fans and former cast members highlight the enduring legacy of Hannah Montana. Earles’ journey from a young actor to a podcast host reflects the show’s lasting influence on his life and career. With the anniversary special, both old and new fans can relive the magic that made Hannah Montana a cultural phenomenon.