Hannah Montana, one of the defining teen television series of the 2000s, rapidly achieved worldwide acclaim by expertly combining catchy pop music with relatable coming-of-age stories. The show not only dominated ratings and sold millions of albums but also inspired extensive global tours and a successful film adaptation. With anticipation growing around a possible 20th-anniversary special, it is timely to revisit the lives and careers of the cast members who became household names through the series. The name Emily Osment Hannah Montana remains closely tied to this memorable era of youth entertainment.
Main Cast Members and Their Career Paths Since Hannah Montana
Miley Cyrus took on the lead role of Miley Stewart, who lived a double life as the famous pop singer Hannah Montana while managing a typical teenage existence. Miley’s natural charisma and the show’s hit songs helped her rise as a prominent Disney star and a beloved youth icon. After the series concluded, Cyrus transitioned into film with roles such as in The Last Song and evolved into a Grammy-winning artist known for her daring music and unique style. Albums like Bangerz and Endless Summer Vacation have cemented her global pop star status.
Actor Cody Linley portrayed Jake Ryan, Miley’s romantic interest who charmed viewers as the appealing on-and-off boyfriend. Linley continued acting after the series, including appearances in Cheaper by the Dozen and competing on Dancing with the Stars. More recently, he has focused on his music career and independent creative ventures.

Moisés Arias played the mischievous Rico Suave, known for his entrepreneurial schemes and teasing of Jackson Stewart. After Hannah Montana, Arias shifted toward more mature and diverse roles, starring in indie films like The Kings of Summer and sci-fi projects such as Ender’s Game. He has built a reputation for choosing unconventional and varied performances, including his part in the first season of Fall Out.
Billy Ray Cyrus, already a celebrated country musician, brought authenticity to his role as Robby Ray Stewart, Miley’s father and manager. His continued relevance in the music scene was highlighted by his collaboration on the viral hit Old Town Road, and he remains active in both music and television appearances.
Mitchel Musso portrayed Oliver Oken, one of Miley’s closest friends who knew her secret identity. Post-Hannah Montana, Musso lent his voice to Jeremy in the cartoon Phineas and Ferb and appeared in the series Pair of Kings. Although he has stepped back from on-screen acting, Musso remains engaged in music and voiceover work.
Jason Earles played Jackson Stewart, Miley’s older brother known for his humorous presence on the show. Afterward, he sustained a Disney connection through his role in the sitcom Kickin’ It and frequently participates in fan conventions and various television projects.
Emily Osment’s Growth Beyond Lilly Truscott
Emily Osment gained widespread recognition for her performance as Lilly Truscott, Miley Stewart’s loyal best friend who helped her balance everyday life with the challenges of stardom. Since Hannah Montana, Osment has matured into roles in popular adult sitcoms such as Young & Hungry and Young Sheldon. Alongside acting, she has pursued her passion for music, steadily building a career that complements her on-screen work.
Continuing Legacy and Future Prospects for the Cast and Series
More than two decades after its debut in 2006, Hannah Montana stands as one of Disney Channel’s most iconic series, profoundly shaping a generation and launching lasting careers for many of its stars. The show’s availability on Disney+ allows new audiences to discover its charm and music. Rumors of a 20th-anniversary reunion have stirred excitement among fans eager to relive the magic and reunite with the beloved cast, including Emily Osment and her co-stars. Such an event would not only honor the show’s legacy but also celebrate the evolution of its cast members over the years.
