‘Hannah Montana’ Anniversary Special: Miley Cyrus’ Secret Disney Boyfriend, How Her Relationship to Hannah Has Changed and Everything Else We Learned

Mar 24, 2026 8:00am PT ‘Hannah Montana’ Anniversary Special: Miley Cyrus’ Secret Disney Boyfriend, How Her Relationship to Hannah Has Changed and Everything Else We Learned By Kennedy French , Payton Turkeltaub 20 years ago, “Hannah Montana” premiered on Disney Channel, introducing a generation of tweens and their parents to the fictional-turned-real popstar who’d go on to sell millions of albums. But, arguably more importantly, audiences met Miley Cyrus, a 13-year-old “country bumpkin,” as she puts it herself. Almost immediately, Cyrus shot to stardom, becoming one of the defining faces of Disney Channel’s golden age. In the years since, she’s continued as an icon in her own right, releasing nine studio albums, selling more than 20 million records worldwide and nabbing 10 Grammy nominations and three wins. But, as the Hannah Montana song goes, “You’ll always find your way back home,” which is why Cyrus returned to celebrate the milestone anniversary (or “Hanniversary”) of the show that made her a star with the “ Hannah Montana 20th Anniversary Special.” With the help of host Alex Cooper and special guests like Tish Cyrus, Billy Ray Cyrus, Selena Gomez and even Chappell Roan, Cyrus retreads her Disney roots, performing hits like “The Climb,” returning to the series’ set and bringing along the fans who have been there from the beginning. Below are all the things we learned from the “Hannah Montana” anniversary special. Cyrus wasn’t the obvious pick for ‘Hannah Montana’ Despite ultimately defining the role, Miley Cyrus was not a unanimous choice. After an 11-month casting process narrowed to two finalists, executives were split. Then-Disney Channel president Gary Marsh made the call, writing in an email that he was “ready to pull the trigger on Miley,” acknowledging, “Is she a risk? Absolutely. Is she a potential star? Absolutely.” Cyrus, who had no prior acting experience, said her authenticity, not polish, is what ultimately set her apart.