Emily Osment Reflects on 'Hannah Montana' 20 Years Later

The actress shares a memento from the Disney Channel series as the show approaches its 20th anniversary.

Published on Feb. 9, 2026

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Emily Osment, who played Lilly Truscott on the hit Disney Channel series 'Hannah Montana', is reminiscing about her time on the show as it approaches its 20th anniversary. Osment shared a photo on Instagram of two scripts - one from a 2007 episode of 'Hannah Montana' and another from her current series 'Georgie and Mandy's First Marriage'. She noted that the 20-year milestone makes her feel 'old', but that she's still doing what she loves. Meanwhile, the show's star Miley Cyrus has teased that big plans are in the works to celebrate the 20th anniversary of the series that launched her career.

Why it matters

The 'Hannah Montana' series was a major hit for the Disney Channel, running for four seasons from 2006 to 2011 and launching the career of its star, Miley Cyrus. The show's 20th anniversary is a significant milestone that will likely be celebrated by the cast and crew, as well as the many fans who grew up watching the series.

The details

In her Instagram post, Emily Osment shared a photo of two scripts - one from a 2007 episode of 'Hannah Montana' and another from her current series 'Georgie and Mandy's First Marriage'. Osment played the role of Lilly Truscott, the best friend of Hannah/Miley and the girlfriend of Oliver Oken, on seasons 3 and 4 of the Disney Channel series. Osment noted that the show's 20-year anniversary makes her feel 'old', but that she's still doing what she loves. Meanwhile, Miley Cyrus, who starred as the titular character, has teased that big plans are in the works to celebrate the 20th anniversary of the series that launched her career.

  • The 'Hannah Montana' series ran for four seasons between March 2006 and January 2011.
  • The show's 20th anniversary will be celebrated in 2026.

The players

Emily Osment

An actress who portrayed Lilly Truscott, the best friend of Hannah and the girlfriend of Oliver Oken, on seasons 3 and 4 of the Disney Channel series 'Hannah Montana'.

Miley Cyrus

The star of the Disney Channel series 'Hannah Montana', who played the dual role of average teenager Miley Stewart and pop star Hannah Montana.

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What they’re saying

“On the heels of our Hannah Montana 20 year milestone, our beloved Georgie and Mandy's First Marriage director Mark Cendrowski brought in his old copy of an HM episode this morning. Proves a few things. First, that I'm old, second that I'm still doing what I love but mostly, MOSTLY that Mark won't leave me alone after all these years and i'm really starting to freak out about it.”

— Emily Osment (Instagram)

“It's so crazy to think, too, that I started as a character that I thought was going to be impossible to shed. And now that's something that when I walk into a space, it's looked at as this sense of nostalgia or something that you have from your childhood, but I've now been as kind of integrated into everyone's life as the character itself. So that's exciting to get to celebrate that.”

— Miley Cyrus (SiriusXM's TikTok Radio)

What’s next

Miley Cyrus has teased that big plans are in the works to celebrate the 20th anniversary of 'Hannah Montana' in 2026.

The takeaway

The 20th anniversary of the hit Disney Channel series 'Hannah Montana' is a significant milestone that will likely be celebrated by the cast and crew, as well as the many fans who grew up watching the show that launched Miley Cyrus' career. The series' enduring popularity and the nostalgia it evokes demonstrate the lasting impact of the show on popular culture.