Drew Roy celebrates Hannah Montana’s 20th anniversary, now flies for Delta

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• 🔥 Quick Facts
• From Bad Boy to Pilot: Drew Roy’s Unexpected Career Transformation
• The Missing Anniversary Celebration: Why Drew Roy Wasn’t There
• How Drew Roy Became a Pilot: A Six-Year Journey of Dedication
• Family Life: Marriage, Children, and Choosing Privacy Over Publicity
• What Does Drew Roy’s Absence Mean for Hannah Montana Fans and Future Reunions?

Drew Roy, who played Miley’s love interest Jesse on Hannah Montana, shocked fans by skipping the 20th anniversary celebration that premiered on Disney+ today, March 24. Instead, the actor-turned-pilot is soaring to new heights, having recently joined Delta Air Lines as a First Officer in February 2025. The surprising career pivot has sparked widespread curiosity about his life beyond Hollywood.

From Bad Boy to Pilot: Drew Roy’s Unexpected Career Transformation

Drew Roy built his early career playing edgy, rebellious characters on Disney Channel and beyond. After Hannah Montana ended in 2011, he landed significant roles in Falling Skies, Timeless, and The Last Ship. He also appeared in films like Sugar Mountain and Secretariat. However, acting was never his true passion. Over the past six years, Roy quietly pursued an entirely different dream, one that required far more dedication than starring in television shows.

His final acting role came in 2021 when he reprised his character Griffin in the iCarly revival. After that project wrapped, Roy made the definitive decision to leave Hollywood behind. According to his social media, his new life consists of two primary loves: flying jets and his family. This stark contrast to his Disney days reflects a man who found his true calling in the cockpit rather than on camera.

The Missing Anniversary Celebration: Why Drew Roy Wasn’t There

Fans erupted on social media when it became clear that Drew Roy would not be appearing in the Hannah Montana 20th Anniversary Special that premiered today on Disney+. The special featured an exclusive interview between Miley Cyrus and podcast host Alex Cooper, along with behind-the-scenes archival footage and musical performances. Other cast members, including Cody Linley who played Jake Ryan, attended the red carpet premiere in Hollywood.

Roy, however, was conspicuously absent from both the star-studded premiere event and the special itself. While Disney did not publicly explain his absence, sources indicate he chose not to participate. Given his commitment to his new career at Delta Air Lines, combined with his preference for a private family life away from the spotlight, the decision aligns with his recent trajectory. His wife Renee Roy remains his biggest cheerleader, celebrating his professional accomplishments on social media rather than seeking red carpet attention.

How Drew Roy Became a Pilot: A Six-Year Journey of Dedication

Career Detail	Information
Training Duration	Approximately 6 years of intensive pilot training
Certification	Qualified jet pilot with commercial rating
First Major Achievement	Promoted to First Officer, Delta Air Lines, February 2025
Spouse’s Comment	“What you have accomplished in the last 6 years, most cannot do in a lifetime”

“From Falling Skies to flying planes. I am so proud of this man. I know absolutely no one that works as hard as you. What you have accomplished in the last 6 years, most cannot do in a lifetime. I’m in awe of this. Of you. You impress me every day. We are truly ecstatic to be a part of the Delta Family. May I present you, Delta First Officer Drew Roy.”

Renee Roy, Drew Roy’s wife, in an Instagram post celebrating his promotion

Family Life: Marriage, Children, and Choosing Privacy Over Publicity

Drew Roy married Renee Gardner in 2015, and the couple celebrated their 10-year anniversary in December 2025. In a heartfelt Instagram post, Renee opened up about their relationship, sharing the ups and downs behind closed doors. She wrote about the fights, career changes, cross-country moves, and postpartum struggles that tested their bond. Despite these challenges, their marriage grew stronger through adversity.

The couple shares two sons and has deliberately kept their children out of the entertainment industry spotlight. Drew’s Instagram bio perfectly summarizes his current priorities: flying jets and loving on my wife and kids. This shift toward family-first values represents a complete reinvention from his days as a teenage television heartthrob. Roy posts rarely but meaningfully, choosing to share aviation moments rather than personal details.

What Does Drew Roy’s Absence Mean for Hannah Montana Fans and Future Reunions?

The Hannah Montana 20th Anniversary Special represents a watershed moment for the beloved Disney series, bringing back Miley Cyrus for her first major public embrace of the character in years. The absence of Drew Roy, who was central to the show’s final seasons and romantic storyline, raises questions about whether future reunions or projects might include him. Roy’s decision to skip the celebration appears intentional and reflective of his boundaries regarding his past career.

For fans who grew up watching Jesse and Miley’s complicated love story unfold across four seasons, Roy’s absence is bittersweet. However, his redirection toward aviation and family suggests he has found genuine fulfillment beyond the entertainment world. Whether he will ever return to act or make special appearances for nostalgia-driven projects remains uncertain. What is clear is that Drew Roy is thriving in his new identity as a pilot and devoted family man, and for him, that is far more rewarding than any reunion could offer.