Hannah Montana 20th anniversary special: More than a decade after Hannah Montana ended its run, the show’s legacy continues to spark nostalgia among fans.
The newly released Hannah Montana 20th Anniversary Special brought that nostalgia back in full force, with Miley Cyrus sharing several surprising revelations about her Disney Channel days.
During a candid conversation with podcast host Alex Cooper, the Grammy-winning singer revisited her early career, relationships, and memories from the iconic series. The special offered fans an intimate look behind the scenes, while also clearing up long-standing rumours that have followed the show for years.
Here are seven of the biggest revelations Miley shared during the special.
1. Dating Dylan Sprouse
One of the most talked-about moments came when Miley confirmed a long-rumoured childhood relationship with Dylan Sprouse. She said, “Dylan was my crush… Secretly, okay, Dylan Sprouse was my boyfriend. I think he was the cutest.”
The pop star explained that the two briefly dated during their Disney Channel years. She even recalled how the Sprouse twins’ father would sometimes take them out for sushi. Miley joked that the situation felt like a “two-for-one,” since Dylan’s twin brother Cole Sprouse often tagged along.
2. Why the Jonas Brothers joined her tour
Another revelation involved the 2007 Best of Both Worlds Tour. Miley shared that the Jonas Brothers ended up opening the tour largely because she was dating Nick Jonas at the time. She explained, “Literally, the reason that the Jonas Brothers were on tour with me was because Nick was my boyfriend, and I wanted to not leave my boyfriend.”
Miley added with a laugh, “So I’d be like, ‘OK, well, I’ll go on tour if my boyfriend can come.’ And they’re like, ‘Cute, have your boyfriend open for the show.’ Boom.”
3. A crush on co-star Mitchel Musso
The singer also admitted she had a crush on her Hannah Montana co-star Mitchel Musso, who played Oliver on the show. Miley joked that after landing the role, she quickly moved on from her hometown crush in Nashville and started paying more attention to her new Disney Channel colleagues.
4. Repairing her relationship with Billy Ray Cyrus
Another emotional highlight came when Miley spoke about reconnecting with her father, Billy Ray Cyrus, who played her dad in the series. She said, “I think when me and my dad are good, people, they feel better.” Reflecting on their complicated relationship in the past, she added, “It just feels good when the Cyruses are getting along.”
5. Taylor Swift x Hannah Montana
Miley also revealed how Taylor Swift appeared in Hannah Montana: The Movie. According to Miley, Swift was cast early in her career because producers wanted someone who could authentically perform in a barn setting.
She joked, “So the way that Taylor Swift ended up in the Hannah Montana movie was because this was kind of the beginning of her career, and they were looking for someone that would authentically, no shade, I guess, be performing in a barn.” Miley also praised Swift for writing the film’s closing track “You’ll Always Find Your Way Back Home.” Calling it timeless, she added, “She ate with that one.”
6. Selena Gomez’s awkward memory
During the special, Miley also reunited with fellow Disney alum Selena Gomez, who appeared in several episodes as rival pop star Mikayla. Gomez recalled feeling uncomfortable wearing heavy makeup for an alien-themed scene. “I remember feeling ugly in that. Because we’re, like, 15 and I want to feel pretty, and I’m like, ‘Ugh.’”
Miley sympathised and responded warmly, reminding viewers that despite their on-screen rivalry, the two stars eventually made peace.
7. Team Jesse or Team Jake?
Finally, Miley addressed one of the show’s most debated questions: whether her character should have ended up with Jake Ryan or Jesse. After some hesitation, she whispered her answer. “Jake.” Explaining her choice, Miley joked, “Because you know what? He’s always out there saying really nice things about me in the press.”
