Lainey Wilson dazzled in a sheer, open-back jumpsuit with dramatic, long sleeves flowing from her wrists as she attended the highly-anticipated Hannah Montana 20th Anniversary Special premiere on Monday evening (March 23).

Wilson, 33, has a personal connection with the beloved character after working as a Hannah Montana impersonator as a teen. She spent weekends performing at birthday parties, where she opened the shows as herself, and transformed into headliner Hannah Montana with a signature blonde wig and costumes inspired by the iconic character. Miley Cyrus, 33, scored her breakout role as the title character of the Disney sitcom — focused on a typical teenager who lives a secret double life as a pop star — that premiered on March 24, 2006. The finale aired on January 16, 2011.

Wilson spoke with Robin Roberts for the Lainey Wilson: Bell Bottom Country special that year. The country star said during that interview that she’d “had a teacher who asked me to put on a Hannah Montana wig and show up at her little girl’s birthday party. Well, of course, I took it too far. I had the wig. I had the portable sound system. And I would open up for myself. …I would be like, ‘Hey y’all, I’m Lainey Wilson, blah, blah, blah.’ I’d sing a few songs that I wrote, and then I’d go backstage or wherever the backstage area was — that might mean somebody’s bedroom at somebody’s house — and throw on my Hannah Montana getup and get out there, and put on like a 15-song concert. I mean, I would do 3-year-old birthday parties one day and I’d be playing (at a) nursing home the next day. So I had to learn, how you speak to 3-year-olds is not how you speak to the elderly. You know, like you have to learn your audience. And it taught me a lot.”

Wilson has since shared her connection to Hannah Montana with Cyrus, including when she covered “The Best of Both Worlds,” a classic Hannah Montana anthem that served as the show’s theme song, in August 2024. Cyrus, then 31, made history as the youngest person to become a Disney Legend at the D23 event. Wilson wrote in a caption on Instagram at the time, “from performing as Hannah Montana on flat bed trailers at birthday parties to honoring the legend herself…now that right there is what ya call a full circle moment. [Miley Cyrus] you’re such an inspiration. Thank you for letting me honor you.” Wilson added later that she’s “incredibly honored to have been a part of such a special night. No one deserved it more than you, sister. Thank you for being you.”

“Those full circle moments where you’re just like, ‘you can’t make this up,’ you know?” Wilson said during a recent appearance on No Filter, an Australia-based interview podcast hosted by Kate Langbroek, when asked about meeting Cyrus. “She’s great. I mean, we know a lot of the same people. I told her, I was like, Hannah Montana meant a lot to me. It kept some money in the bank for five years for me. She has influenced more people than I think that she even realizes. …I think she is a rock star. She’s a rock star.”

The Hannah Montana 20th Anniversary Special is streaming on Disney+ and Hulu as of Tuesday (March 24). See photos of Wilson’s premiere look below.

Wilson is among the country artists nominated at the 2026 iHeartRadio Music Awards, returning this spring to Dolby Theatre in Los Angeles, California. She’s also taking the stage during the show. See the list of country artists nominated here, and find additional details (including the lineup) here.

Like in years past, iHeartRadio is letting the fans choose the winners in several new and established categories. Fan voting will determine this year’s Favorite Broadway Debut, Favorite TikTok Dance, Favorite Debut Album, Best Lyrics, Best Music Video, Favorite On Screen, Favorite Tour Photographer, Favorite Soundtrack, Favorite Tour Style, Favorite Tour Tradition and Favorite K-pop Collab. Social voting begins on January 8th, and will close on March 19th at 11:59pm PT for all categories. Fans can vote by visiting iHeartRadio.com/awards.

Tune in to see which artists will take home an iHeartRadio Music Award on Thursday, March 26th at 8pm ET live (PT tape-delayed) on FOX. The show will also be broadcast on iHeartRadio stations across the country and on the iHeartRadio app.

Andy Woods