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Miley Cyrus’ Hannah Montana 20th Anniversary Special: 7 Best Moments

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If you grew up hooked on Hannah Montana, Miley Cyrus has a very special nostalgic present you’re going to absolutely love.

To commemorate 20 years since she first donned that iconic blonde wig, the Grammy winner recently took part in an exciting anniversary special, which premiered on Disney+ in the early hours of Tuesday morning.

Over the course of the hour-long special, Miley revisited the classic Disney Channel series, performing iconic songs from its soundtrack, taking part in one-off skits and interviews and reuniting with almost the entire cast.

Here are seven of the biggest highlights from Hannah Montana’s 20th anniversary special, including stand-out performances, surprise revelations and A-list guests…

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1. It turns out Miley Cyrus almost missed out on the role of Hannah Montana completely

Miley Cyrus’ long and complicated road to being cast as Hannah Montana is a well-documented one, with the child performer originally auditioning when she was far too young for the part, only to be asked back around a year later when producers deemed they couldn’t find anyone as good as her.

However, what fans might not realise is just how close Miley came to not being cast in the show at all.

Former Disney exec Gary Marsh recalled: “We were down to the last two girls, and you were this 12-year-old pistol, raw and real, and fresh out of Tennessee. And you both left… there [were] 10 people in the room, and we took a vote. It was not a landslide.

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“People put forth their real opinion, and I had made a decision, and I wrote an email to the team. It said, ’we pride ourselves not just on creating great television, but on creating stars. I’m ready to pull the trigger on Miley. Is she a risk? Unquestionably true. Is she a potential star? Absolutely.

“’And whatever comes of this decision, I’m thrilled that all of us will be able to sit down over a drink in a few years and remember this moment when we decided to forsake the safe route for the riskier one and the greater reward’.”

2. Miley Cyrus had a surprising revelation about dating a fellow child star during her Hannah Montana days

Dylan Sprouse was my boyfriend,” Miley admitted, referring to the child star, who at the time was known for The Suite Life Of Zac & Cody and his work as Ben on Friends. “I think he was the cutest.”

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She added that Dylan and his twin brother Cole Sprouse’s father “would take us to sushi”.

Miley quipped: “It was a two-for-one. Like, bring the brother. Hello!”

Cole and Dylan Sprouse at Miley Cyrus’ 16th birthday party in 2008

Jim Smeal/BEI/Shutterstock

The future chart-topper would go on to share the screen with her childhood sweetheart in a cross-over episode between Hannah Montana, The Suite Life Of Zac & Cody and That’s So Raven.

3. Miley Cyrus also had a great story about how Taylor Swift came to write music for the Hannah Montana movie

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As well as writing songs for Hannah Montana: The Movie, Taylor Swift also made a cameo in the 2009 film.

“This was kind of the beginning of her career,” Miley recalled in the new special. “They were looking for someone that would authentically – no shade – be performing in a barn.”

She continued: “We both performed in the barn, and so she came into the performance, and she had written a song for the Hannah Montana movie, maybe even two. But she actually wrote the finale song, You’ll Always Find Your Way Back Home.”

“Credit where credit’s due. She ate with that one,” Miley added.

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Miley Cyrus praises Taylor Swift and says her pen stands the test of time 💛

“She actually wrote the finale song [For Hannah Montana The Movie]. Credit where credit’s due. Banger. Stands the taste of time. She ate with that one” pic.twitter.com/4SAFn7dvgZ

— Miley Official (@MileyCyrusBz) March 24, 2026

4. Miley Cyrus was also reunited with another fellow Disney alum in the Hannah Montana special: Selena Gomez

Miley and Selena Gomez started their careers around the same time, with the latter appearing in Disney projects like Wizards Of Waverly Place around the time Hannah Montana was becoming a TV and musical phenomenon.

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Selena even appeared in three episodes of the show as Mikayla, a rival pop star to Hannah Montana.

As a surprise for Miley during one segment, Selena made an impromptu appearance in the anniversary special, where they reflected on their early starts on the Disney Channel.

“The whole Meet Miley album was my life,” the Only Murders In The Building star enthused. “You created culture, babe!”

5. The Hannah Montana special also featured an unexpected appearance from Chappell Roan

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One thing producers managed to keep under wraps before the special was that it would feature a short interview between Miley and woman of the hour, Chappell Roan, who was a Hannah Montana superfan growing up.

During their conversation, the Pink Pony Club singer also thanked Miley for her contributions to pop culture, claiming: “You walked so I could run. What I do on stage [or] when I go on a red carpet and I can just be… that’s because you took a lot of heat for that in 2012 and 2013. I don’t have to deal with that as much because the world took it out on you.”

Chappell added: “I’m so grateful that I get to be a part of this – I mean, I grew up watching Hannah at my grandparents’ house. It just means so much and I’m so grateful to you.”

Chappell Roan makes Miley Cyrus cry and thanks her for changing culture:

“You walked so I could run. I can go on a red carpet [naked] because you took a lot of the heat. I don’t have to deal with it as much, the world took out on you. I grew up with Hannah Montana.” pic.twitter.com/kQAhlDib8I

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— Miley Official (@MileyCyrusBz) March 24, 2026

6. Of course, the Hannah Montana special featured plenty of musical performances, but this rendition of The Best Of Both Worlds is what fans have really been waiting for

We’re definitely going to have that on repeat for the foreseeable…

7. And in case you’re wondering, yes, Miley Cyrus can still Hoedown Throwdown with the best of ’em

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Once you’ve popped it, locked it and, indeed, polka dotted it, you clearly never forget it.

Hannah Montana: 20th Anniversary Special is now streaming on Disney+.

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