Miley Cyrus took the opportunity to reminisce about her early career during the “Hannah Montana 20th Anniversary Special,” which premiered on March 23, 2026, in Los Angeles. The beloved Disney Channel series, which aired from 2006 to 2011, catapulted Cyrus to fame as she juggled the dual roles of a pop star and a typical teenager. The special, now available on Disney+ and Hulu, featured a range of behind-the-scenes secrets, surprise guest appearances and a musical performance by Cyrus that generated significant excitement among fans.
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In a candid interview with Alex Cooper, host of the “Call Her Daddy” podcast, Cyrus reflected on her time working alongside various Disney stars. One of the most surprising revelations was her secret romantic involvement with fellow actor Dylan Sprouse of “The Suite Life of Zack & Cody.” Cyrus fondly recalled her crush, stating, “Secretly, okay, Dylan Sprouse was my boyfriend. I think he was the cutest.” Their outings typically included sushi dinners supervised by his father and accompanied by his twin brother Cole, adding a wholesome context to their youthful romance.
The special also delved into the making of the “Hannah Montana: The Movie,” where Taylor Swift made an unforgettable appearance. Cyrus reminisced about how the filmmakers wanted to feature a performer who could naturally fit into the film’s setting, explaining, “They were looking for someone that would authentically… be performing in a barn.” Swift’s performance of “Crazier” during the barn dance scene became iconic, and Cyrus referred to one of the film’s songs, “You’ll Always Find Your Way Back Home,” as a classic that “stands the test of time.”
As her music career progressed, Cyrus acknowledged the personal connections she had fostered during her time on Disney. At the height of her fame, she began dating Nick Jonas, who was part of the emerging Jonas Brothers. During this period, Cyrus arranged for her then-boyfriend and his brothers to open for her on the “Best of Both Worlds Tour.” She admitted to making this decision so she could have him by her side while touring, highlighting the young couple’s sweet yet complicated relationship.
Reflecting on her past, Cyrus also shared some of her teenage crushes, revealing her infatuations with her co-stars. She mentioned feeling drawn to Mitchel Musso, who played her best friend on “Hannah Montana,” and later developed a crush on Zac Efron, acknowledging the youthful excitement of navigating friendships and their complexities in the spotlight.
Accompanying Cyrus in the anniversary special was her long-time friend Selena Gomez, who played Mikayla, her character’s rival on the show. Gomez offered a humorous take on her memories of filming, notably recalling her discomfort in her character’s makeup. The playful banter between the two friends during the special underscored their enduring friendship and camaraderie formed since their Disney days.
In a surprise addition to the event, singer Chappell Roan expressed heartfelt gratitude to Cyrus for paving the way for younger artists. Roan credited Cyrus for her courage and resilience in the industry, thanking her for making it easier for her and other artists to navigate their careers. This moment highlighted Cyrus’s influence on the next generation of performers and the personal growth they have both experienced since their early days in entertainment.
Cyrus concluded the special on a rich emotional note, performing a new song, “Younger You,” which she dedicated to her child self and the journey she has undertaken since her “Hannah Montana” days. She reflected on celebrating two decades since the show’s inception, expressing gratitude for the experiences it afforded her. “It’s been an honour to celebrate 20 years with Hannah Montana, and I’ve looked back at every memory with a heart full of love,” Cyrus shared, reminding fans of the impact that the beloved character had on her life and career.
The “Hannah Montana 20th Anniversary Special” not only provided a nostalgic look back at a pivotal moment in pop culture history but also served as a testament to profound personal growth and evolution for Miley Cyrus and her fellow cast members. With heartfelt stories, revelations, and a reminder of the legacy of “Hannah Montana,” the special resonated with a generation that grew up during a significant era in children’s television.