Billy Ray Cyrus sits in the family room of his brother's house, which lies next to his own sprawling property in the bucolic hinterlands of Nashville.

He's talking about Old Town Road, then in its 19th week at the top of the charts, the longest such streak in history. It still feels unstoppable, but Cyrus senses its record-shattering run is almost over, and he's right. Within days, he and Lil Nas X will be deposed by Billie Eilish's Bad Guy.

But the unlikely collaboration between the 58-year-old country singer from Flatwoods, Kentucky, and the 20-year-old rapper from Atlanta was still the unquestioned soundtrack of northern summer, ascending from viral smash to mainstream hit to world-eating cultural phenomenon.

It created a special bond between the pair, which makes sense because Cyrus is one of the few people who can understand the very peculiar position now occupied by Lil Nas X.


Achy Breaky Heart was the Old Town Road of its day, a genre-bending, gatekeeper-offending, once-in-a-generation crossover sensation that changed the culture forever.

"This young man had clearly defined exactly what he wanted to happen, and that's the way you reach your dreams," Cyrus says.

Cyrus is serious and polite and peppers his conversation with a mixture of backwoods mysticism, shrewd observations on the entertainment industry and Dale Carnegie-esque inspirational sayings.

He believes in intuition, and spirits.

Lil Nas X, left, and Billy Ray Cyrus accept the song of the year award for
Lil Nas X, left, and Billy Ray Cyrus accept the song of the year award for "Old Town Road" at the MTV Video Music Awards. Photo / AP

He has also been at the forefront of the cultural conversation at three pivotal and very different points in the past 30 years: For Achy Breaky, for the Disney Channel smash Hannah Montana, in which he played the father of his real-life daughter Miley, and Old Town Road. But he was always here, plugging along, even when the conversation turned away. He has been directed by David Lynch and befriended by George Jones, and he just performed at Glastonbury.

Unlike Friends or the Spice Girls, Achy Breaky Heart was a piece of 90s pop culture few felt nostalgic for.

"I wish Billy Ray Cyrus would make a comeback" is not something anybody has ever said out loud, probably not even Billy Ray Cyrus.

Lil Nas X didn't care about any of that, or maybe he just didn't know. He had grown up with Hannah Montana, and Cyrus was one of the few country singers he was familiar with. In December, hoping to create a viral moment for his new country-trap song, he tweeted in Cyrus' direction ("Twitter please help me get Billy Ray Cyrus on this").


In mid-March, Cyrus got an email from an executive at Columbia Records, asking whether he would listen to a track by a young Atlanta artist named Lil Nas X. It had a link to a site called TikTok. Cyrus was mystified. "I'm going, 'Who is Lil Nas? And what is TikTok?' "

TikTok, Cyrus soon discovered, was a social media app specialising in highly meme-able homemade videos.

He spent hours studying Old Town Road. "It was different for me, but I loved it." Hip-hop artist and songwriter Jocelyn "Jozzy" Donald worked with him on his guest verse. Jozzy told Cyrus her mom had a crush on him during the Achy Breaky years. He didn't seem to find it surprising. Everybody's mom did.

Jozzy told Cyrus she wanted him to approach the song as a rapper would. "I said, 'We're going to role reverse,' "Jozzy recalled. "You're going to be Magic Johnson, and Lil Nas is going to be Larry Bird."

About this time the original version of Old Town Road was deemed insufficiently country, and it was removed from the Billboard country charts.

"I started freaking because something inside my spirit knew that this was a special moment, and something very important in my life," Cyrus recalls. "My spirit was just going crazy, and I kept pushing. It just looked like it was going to go away."

Billy Ray Cyrus salutes the crowd at the Canadian Country Music Awards in Calgary. Photo / AP
Billy Ray Cyrus salutes the crowd at the Canadian Country Music Awards in Calgary. Photo / AP

When the remix landed atop the Billboard Top 100 a few weeks later, it wasn't just a hit, it was a populist uprising. And it was something that looked familiar. "The country world was trying to do to Lil Nas exactly what they did to Billy Ray Cyrus with Achy Breaky," Jozzy says. "This was his redemption, a little bit."

Growing up in Kentucky, Cyrus played baseball. He wanted to go pro, but when a voice inside his head told him he would be a musician instead, he listened. "When I traded that catcher's mitt in and bought a left-handed guitar, I didn't look back." For 10 demoralising years, he struggled. He got married, got divorced and built up a local following. During a now-legendary stand at the Ragtime Lounge in Huntington, West Virginia, he played to full houses every night, an early version of the international celebrity that would follow.

Closing in on 30 he played his song Some Gave All, an ode to veterans Cyrus views as the most consequential song of his career, for Harold Shedd at Mercury Records and got a record deal on the spot.

His first single was a goofy, danceable ear worm called Don't Tell My Heart. At least that's what it was called until Cyrus politely suggested renaming it Achy Breaky Heart.

Cyrus and the song's writer, Don Von Tress, soon became close friends. "I was struck by his charisma and his honesty," Von Tress recalls.

Cyrus approached his impending stardom like he was training for the pursuit of a sports championship. He quit drinking, for one thing. "To this day, I can't even drink a beer or nothing," he says.


Achy Breaky was instantly polarising. Pop fans embraced it as a novelty hit. Country purists saw it as degrading and ridiculous. His debut album went on to sell 9 million copies.

Success was alienating. Cyrus toured and recorded nonstop.

Artists often have complicated relationships with the hits that made them famous: Sometimes a song isn't representative of their body of work, or it's embarrassing, or they just tire of it. Ask Cyrus whether this might be the case for him, and he looks incredulous. "Are you crazy?"

Cyrus had enough post-Achy Breaky hits to fend off official one-hit-wonder status, but by the release of his third album, country radio no longer welcomed him. His father suggested he reinvent himself as an actor, like Kenny Rogers and Dolly Parton did.

Parton — who embraced the entire Cyrus family, which grew to include his second wife, Tish, and six kids. (Dolly is godmother to Miley.) — also urged him to diversify. Cyrus set his mind to acting and soon found himself with a small part in Lynch's 2001 mind-bending masterpiece, Mulholland Drive.

He went on to play a small-town doctor who moves to the big city in the Pax network series Doc, which ran for 88 episodes. In 2005, he was cast as Robby Stewart in Hannah Montana, opposite a tweenage Miley.


The series launched his daughter into orbit and gave Cyrus a new public identity: Miley's dad.

Now Cyrus is enjoying his third foray into pop cultural relevancy in as many decades. He's very famous again, but it's an odd kind of fame: It's his, but not his. He's Hannah Montana's dad, Lil Nas X's sidekick. He has begun writing songs again. "I may just have peace of mind for the first time ever."