Then and Now: Hannah Montana stars Miley Cyrus, Emily Osment and more through the years

The cast of Hannah Montana reunited on March 23 for the premiere of the 20 years reunion special of their beloved show. Ahead of the special, we take a look at how the cast of the Miley Cyrus show have transformed in the last two decades

Updated On: 2026-03-24 02:42 PM IST

Compiled by : Athulya Nambiar

Hannah Montana

Miley Cyrus — Miley Stewart / Hannah Montana

Miley Cyrus played the lead role of Miley Stewart, a regular Malibu teenager living a secret double life as global pop star Hannah Montana. The character balanced school, friendships, and fame while hiding her superstar identity from the world. Her journey revolved around growing up, family bonds, and the pressures of celebrity life

Miley’s emotional arc, music performances, and comedic timing made her the heart of the show. The role turned Cyrus into a worldwide teen icon and launched her music career. Today, she is a Grammy-winning global pop star known for hits like Flowers and bold artistic reinventions

Emily Osment — Lilly Truscott / Lola

Emily Osment played Lilly Truscott, Miley’s loyal best friend who later adopts the alter ego Lola Luftnagle.
Lilly is quirky, energetic, and fiercely protective of Miley and her secret

The friendship between Lilly and Miley became one of the show’s emotional anchors. Osment later built a steady TV career and currently stars in the sitcom Georgie & Mandy’s First Marriage

Jason Earles — Jackson Stewart

Jason Earles portrayed Jackson Stewart, Miley’s older brother and the family’s resident prankster.
Known for his goofy humor and laziness, Jackson often landed in ridiculous situations. Despite sibling squabbles, he deeply cared for Miley and often helped protect her secret

Earles continues acting in Disney projects and family comedies, staying active in television

Moises Arias — Rico Suave

Moises Arias played Rico Suave, the mischievous child entrepreneur who owned the beach shack.
Rico frequently bossed around Jackson and schemed to make more money. His sarcastic wit and mini-tycoon attitude made him a memorable side character

Rico’s antics added sharp comic relief and rivalry-driven humour. Arias later transitioned into indie films and fashion, earning acclaim for offbeat roles

Anna Maria Perez de Tagle & Shanica Knowles — Ashley Dewitt & Amber Addison

Anna Maria Perez de Tagle and Shanica Knowles played Ashley and Amber, the school’s fashionable mean-girl duo. They were Miley and Lilly’s stylish but shallow classmates. Known for their “Oh my gosh” catchphrase, they delivered iconic comic sass

Their exaggerated high-school drama added satirical humour to teen culture. Both actresses later worked in television, music, and stage projects

Billy Ray Cyrus — Robby Ray Stewart

Billy Ray Cyrus played Robby Ray Stewart, Miley’s widowed father and manager.
A former country singer, he guides Miley through fame while raising his children.
Robby is warm, wise, and often delivers heartfelt life lessons

The real-life father-daughter chemistry added authenticity to the show. Cyrus continues making country music and acting in television and film projects

Cody Linley — Jake Ryan

Cody Linley portrayed Jake Ryan, a teen heartthrob actor and Miley’s on-again, off-again love interest.
Jake struggles to maintain a normal teenage life while being famous. His romance with Miley became one of the show’s central relationship arcs

Jake’s appearances often triggered emotional turning points in Miley’s life. Linley later appeared in TV films, reality shows, and continues creative media work

Mitchel Musso — Oliver Oken

Mitchel Musso played Oliver Oken, Miley’s dramatic and talkative best friend. Oliver idolised Hannah Montana before discovering Miley’s secret identity. His over-the-top personality and loyal friendship added chaotic comic energy

Oliver’s band and romantic subplot with Lilly became key storylines. Musso later pursued music and voice acting, including Disney animated series roles

The Hannah Montana 20 year reunion special is now streaming on JioHotstar in India

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