Nothing short of a busy week for Lainey Wilson, the country star dazzled on the red carpet as she attended the Hannah Montana 20th Anniversary Special on Monday. The night celebrated the career of Miley Cyrus and how she helmed the popular series for the Disney network. It seemed that Wilson and Cyrus once again crossed paths at the 2026 iHeartRadio Music Awards. But this time, the spotlight was on Wilson as she took the stage to add a little country to the event.

Kicking the night off, Ludacris returned to the iHeartRadio Music Awards to host. Last hosting the ceremony in 2024, the rapper received a massive honor when it was announced he would be given the iHeartRadio Landmark Award for his contributions as a pioneer in hip-hop. Much like Ludacris, Wilson was wearing several hats throughout the evening. Standing on stage, Wilson performed “Wildflowers and Wild Horses”, “Heart Like A Truck”, and “Hang Tight Honey.”

But before celebrating and heading to the afterparty, Wilson showcased the talents that landed her a spot in country music. And to make it better, Cyrus was only a few feet away. Honored with the iHeartRadio Innovator Award, Miley Cyrus watched on as Wilson brought a dose of country grit to the stage, turning the moment into a full-circle celebration of two artists.

The Deep Connection Between Lainey Wilson And Miley Cyrus

While not one to hide her past, Wilson often discussed the inspiration she received from Cyrus. While attending the Hannah Montana celebration, the singer explained how a teacher once asked a student to dress up as the character for her daughter’s birthday. That single request changed Wilson’s entire life.

“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.”

While juggling her dream of being a country singer and cosplaying Hannah Montana, Wilson quickly learned about the stress, commitment, and determination it takes to succeed in the music industry. “ 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.”

Now standing on one of music’s biggest stages at the iHeartRadio Music Awards 2026, Wilson proved just how far those early lessons have taken her. And with Cyrus watching, it was a reminder of where the journey began, and just how far Wilson has come.