Billy Ray Cyrus Traces 'Old Town Road' Success With Lil Nas X Back to 'Hannah Montana'

It was 27 years between Billy Ray Cyrus' first CMA Award, and his second. In 1992, Cyrus won Single of the Year for "Achy Breaky Heart," winning his second at the 2019 CMA Awards, for Musical Event of the Year, for "Old Town Road" with Lil Nas X. His first award had to do with his talent, as did his second, although he acknowledges "Old Town Road" would have never happened for him if he hadn't starred alongside his daughter, Miley Cyrus, in Hannah Montana years ago.

"Little did I know that sitting back in Atlanta, while I was being Robby Ray and doing Hannah Montana, there was a little boy who had big dreams in Atlanta, and 10 years later our paths crossed," Cyrus told PopCulture.com and other media, backstage at the CMA Awards with Lil Nas X. "And because of Hannah Montana, he said, 'Can anybody get this song to Billy Ray Cyrus?' So for me, in a lot of ways, it's just kind of a reminder to do the best you can do, do what you do because you'll love it and you never know who's watching."

"Old Town Road" began climbing the charts at country radio earlier this year, before the song was banned for not being country enough. Fans still latched onto "Old Town Road," making it one of the few songs over the years that has won a CMA Award without being on radio. An anomaly for some, but normal for Cyrus.

"It's perfect for my career," Cyrus maintained. "The fact that the award that I win, the Event of Country Music was a song that was banned, and I think that best describes kind of my journey. I've never been one to really fit in, and never really wanted to do my own thing and make my own musical style. Waylon Jennings said Johnny Cash, [Willie] Nelson being an original ... Johnny Cash had said to me once about, 'Don't live your life like trying to fit in the box. Don't try to fit outside the box. Live it like there is no box. '

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"And I think that's one thing I brought to the table," he continued. "In his thinking was like, 'There is no box. There are no rules, no limits, no preconceived notions. Music is music and it's all about the fans.' And that's what this song, 'Old Town Road' was. It was the fan song. It was the people's song. It really wasn't about what critic agreed with it or what one tried to define it one way or another. It's what people like. That's what a hit is."

Photo Credit: Getty / Dimitrios Kambouris

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