It feels like just yesterday that we were tuning into the Disney Channel to watch Miley Stewart navigate her double life as a pop superstar. But believe it or not, the iconic series Hannah Montana first graced our screens 20 years ago, premiering on March 24, 2006. The show quickly became a global phenomenon, catapulting its young star, Miley Cyrus, into international superstardom. As the 20th anniversary approaches, it’s the perfect time to look back at how Miley and the rest of the beloved cast have evolved since their days in the sparkly world of Hannah Montana.
Miley Cyrus, who was just 12 years old when she landed the role of Miley Stewart/Hannah Montana, has openly reflected on her journey from child star to a multifaceted artist. Her 2023 single “Used To Be Young” offered a poignant and honest look back at her “wild” younger years, filled with both nostalgia and a mature perspective. Now, with new music and visual projects continuing to make waves, Miley is set to appear in a special Hannah Montana reunion on Disney+ to commemorate the show’s milestone anniversary. Engaged to musician Maxx Morando, she remains a significant force in the entertainment industry, while Hannah Montana continues to captivate new generations, with all episodes available for streaming on Disney+.
Miley Cyrus: From Teen Idol to Global Superstar
Miley Cyrus’s transformation since her days as Hannah Montana is nothing short of remarkable. Her role as the titular character in the Disney Channel series, which ran for four seasons from 2006 to 2011, not only made her a household name but also a massive teen idol. She even reprised her role in the 2009 film, Hannah Montana: The Movie, further solidifying her status.
After her Disney tenure, Miley embarked on a highly successful music career, releasing a string of critically acclaimed albums such as Bangerz, Plastic Hearts, and Endless Summer Vacation. Her discography boasts numerous chart-topping singles, including “The Climb,” “Party in the U.S.A.,” “Wrecking Ball,” and the global hit “Flowers.” Her 2023 single “Used to Be Young” marked a significant moment of reflection, offering fans a glimpse into her personal growth and her perspective on her formative years. Miley has also continued to explore her artistic expression through visual albums, with her 2025 project Something Beautiful earning considerable critical attention.
Beyond music, Miley has also continued to act. She starred in the 2010 drama The Last Song, a role that famously led to her meeting ex-partner Liam Hemsworth. More recently, she made a notable appearance in an episode of the acclaimed anthology series Black Mirror, showcasing her versatility as a performer.
The Supporting Cast: Where Are They Now?
While Miley Cyrus was undoubtedly the star of Hannah Montana, the show wouldn’t have been the same without its vibrant supporting cast. Let’s take a look at what some of the other key players have been up to since the show wrapped.
- Emily Osment (Lilly Truscott/Lola Luftnagle): Miley’s best friend and partner-in-crime, Lilly, was played by Emily Osment. After Hannah Montana, Osment continued her acting career with roles in films like Kiss Me and Dadnapped. She also lent her voice to the animated series Family Guy and starred in the ABC Family (now Freeform) sitcom Young & Hungry. More recently, she’s been a prominent figure in the world of voice acting, notably as the voice of Sandy Cheeks in SpongeBob SquarePants and as the lead in the Netflix series The Kominsky Method.
- Jason Earles (Jackson Stewart): Miley’s older brother, Jackson, provided much of the comedic relief. Jason Earles has remained active in television, appearing in shows like Kickin’ It and Hotel Du Loone. He also reprised his role as Jackson Stewart in the Hannah Montana spin-off series So Random!. Earles has also ventured into directing and producing, showcasing a broader range of talents behind the camera.
- Billy Ray Cyrus (Robby Ray Stewart): Playing Miley’s father and manager, Robby Ray, Billy Ray Cyrus brought his country music charm to the show. He continued to release music and tour extensively after Hannah Montana. He also starred in the CMT sitcom Still the King and has made notable appearances in films. His personal life has also been a frequent topic of public discussion in recent years.
- Mitchel Musso (Oliver Oken/Mike Standley): Oliver, Miley’s other best friend, was portrayed by Mitchel Musso. Musso also pursued a music career, releasing albums and singles. He continued acting in Disney Channel projects, including the series Pair of Kings. While his acting career has been less prominent in recent years, he remains a beloved figure from the
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