Drew Roy Reflects on ‘Hannah Montana’ After Miley Cyrus’ Anniversary Comments

Drew Roy, who portrayed Jesse on the Disney Channel’s hit series Hannah Montana, recently addressed the show’s 20th anniversary and comments made by Miley Cyrus during the celebration. Roy shared his gratitude for the opportunity and provided an update on his life, although his wife subtly responded to his absence from the anniversary special.

Celebrating Two Decades of ‘Hannah Montana’

The 20th anniversary of Hannah Montana sparked a wave of nostalgia, but also some discussion surrounding the show’s cast and relationships. Roy took to Instagram on April 1, 2026, to express his appreciation for the experience. “Twenty years? Wow, it’s hard to believe,” he said in a video posted to his account. “Although, looking at my face it makes sense. But, seriously, I had to come on and say thank you.”

Roy emphasized the impact the show had on his life, noting he came from a modest town and was grateful for the opportunity to work alongside the talented cast, including Miley Cyrus and Emily Osment. He fondly remembered his role as Jesse, Hannah Montana’s band member and eventual love interest. US Magazine reports that Roy described the experience as “incredible.”

The Love Triangle and Miley’s Preference

During the Hannah Montana 20th Anniversary Special, Miley Cyrus revisited the iconic love triangle between Hannah/Miley Stewart, Jake Ryan (played by Cody Linley) and Jesse. Cyrus ultimately declared her preference for Jesse, stating he aligned more with her personality, while Jake suited Hannah’s character. First Curiosity notes that Linley acknowledged his character’s actions hurt Cyrus.

Where is Jesse Now?

Roy’s recent Instagram post also served as a life update. While he didn’t detail his current profession, he mentioned he is now a husband and a father of two. His wife, Rennee Roy, addressed his absence from the anniversary special on Instagram, explaining the family’s decision to prioritize a quieter life away from the spotlight. The Tab reports that Rennee explained they moved to a location where their sons could grow up with family and enjoy a more normal childhood.

Rennee highlighted Drew’s continued passion for acting and his appreciation for the opportunities he’s had, emphasizing that he cherishes the memories and relationships formed during his time on Hannah Montana.

A Lasting Legacy

Despite the years that have passed, Hannah Montana continues to resonate with fans. Drew Roy’s recent comments and his wife’s statement demonstrate the enduring impact of the show and the lasting connections forged by its cast and crew. The anniversary celebration has reignited interest in the series and prompted reflection on the characters and storylines that captivated audiences two decades ago. Yahoo Entertainment covered Roy’s initial response to the anniversary and Cyrus’ comments.