Billy Ray Cyrus near his ranch, enjoying his third moment of superstardom, which came via “Old Town Road.” (Nathan Morgan for The Washington Post)

On this hot August morning, Billy Ray Cyrus sits in the family room of his brother’s house, which lies adjacent to his own sprawling property in the bucolic hinterlands of Nashville. He’s talking about — what else? — “Old Town Road,” then in its 19th week at the top of the charts, the longest such streak in history. At this moment, it still feels unstoppable, but Cyrus, a longtime student of chart positions, 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, Ky., and the 20-year-old rapper from Atlanta was still the unquestioned soundtrack of 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 currently 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 approvingly.

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. He looks for signs in things. He’s a you-miss-one-hundred-percent-of-the-shots-you-don’t-take kind of guy.

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

Unlike “Friends” or the Spice Girls, “Achy Breaky Heart” was a piece of ’90s pop culture few people 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 only country singers he was familiar with. In December, the rapper, hoping to create a viral moment for his brand-new country-trap song, tweeted in Cyrus’s 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. There was an accompanying 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 specializing in highly meme-able homemade videos. He was mad at himself for not already knowing that. “I’m a student of the game. I should have known what TikTok is. I’m always looking for the next competitive edge.”


Cyrus and his “Old Town Road” collaborator, Lil Nas X. (Frazer Harrison/Getty Images for Stagecoach)

Cyrus made plans to enter the studio the next day. He spent hours studying “Old Town Road” like it was homework. “[I] learned it really good,” he says, “because it was different for me, but I loved it.”

Cyrus was paired with hip-hop artist and songwriter Jocelyn “Jozzy” Donald, who worked with him on his guest verse. Jozzy told Cyrus that her mom had a crush on him during the “Achy Breaky” years, which he didn’t seem to find 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. We’ve gotta get you the hottest bars.’ ”

It was around this time that the original version of “Old Town Road” was deemed insufficiently country, and it was removed from the Billboard country charts. The decision brought usually subterranean issues of race and genre in the music industry into the daylight. Cyrus says he can’t really speculate on those, but he knew that whatever was happening wasn’t good. He was also worried that, as the designated country guy, his services would no longer be needed on a song he felt a connection to. “I started freaking because something inside my spirit knew that this was a special moment, and something very important in my life,” he recalls. “My spirit was just going crazy, and I kept pushing. It just looked like it was going to go away.”

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,” he says. For 10 demoralizing years, he struggled. He briefly moved to Southern California in search of a record deal and became a successful car salesman instead. He returned home, got married, got divorced and built up a local following. During a now-legendary stand at the Ragtime Lounge in Huntington, W.Va., he played to overflow crowds every night, an early version of the all-encompassing international celebrity that would follow.

Cyrus could have reigned there indefinitely, but he was closing in on 30, and he worried that if he didn’t get a record deal soon, he never would. And he was starting to get a bad feeling about the Ragtime. “I felt like I was gonna die,” Cyrus recalls. He means it literally. “The bar was getting pretty rough, and it was getting so packed, it was uncontrollable. Like, every single night, you just couldn’t get people in there. It was getting crazy.”


Cyrus at the height of “Achy Breaky Heart” mania in 1992. (Mark Humphrey/AP)

His intuition also told him something good was about to happen. He played his song “Some Gave All,” an ode to veterans that Cyrus views as the most consequential song of his entire 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, who had field-tested the song for audiences at the Ragtime, 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. “Back in the day when everybody had to have a Stetson stapled to their forehead, here’s this guy with a mullet and a cut off sweatshirt and high-top tennies.”

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. “My inner voice said, ‘You’re gonna have to really be on top of your game, and alcohol could be a problem.’ . . . I just quit. If I hadn’t, it’d be a different deal for me. I don’t think I’d even be alive. (Then) ‘Achy Breaky’ came out, and I just ran with it.”

“Achy Breaky” was instantly polarizing. Pop fans embraced it as a novelty hit. Country purists saw it as degrading and ridiculous. (That the accompanying video, featuring a hip-swiveling Cyrus, helped set off a nationwide line-dancing craze somehow made it worse.) His debut album went on to sell 9 million copies.

Success was alienating. Cyrus toured and recorded nonstop, with Von Tress his frequent collaborator and travel companion. It was hard for them to relate to anybody else. “We were right in the middle of that tornado,” Von Tress recalls. “When it exploded, it was just mind-boggling. It dominated everything.”

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?” he asks. “Are you nuts? Don’t ever think that about me.”

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. “I said, ‘I’m not an actor,’ ” Cyrus recalls. “And he said, ‘I’m sure it’s just like everything else. You just gotta start. You’ll learn.’ ”

Parton and Cyrus had been friends for years. Parton embraced the entire Cyrus family, which grew to include his second wife, Tish, and six kids. (Dolly is godmother to Miley.) Parton describes Cyrus in an email thusly: “He’s tender but tough, pretty but rugged, mysterious but personable. He’s a man’s man but definitely a woman’s kind of guy! Oh, and did I mention he’s talented? He’s a great singer, songwriter, and entertainer. I’ve loved him from the start.”

Parton 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.” The director proved influential in molding the singer’s minimalist acting style. “He was encouraging,” Cyrus remembers. “I had him on such a high pedestal because I was such a fan.”

Cyrus 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, who played a pop star undercover as an ordinary girl.

The series launched his daughter into orbit and gave Cyrus a new public identity: Miley’s dad. (Five days before this interview, Miley and husband Liam Hemsworth announced their separation; Cyrus doesn’t talk much about Miley.)

Working together drew father and daughter closer, even if the circumstances were unnatural. “It’s obviously incredibly unusual for a tweenage girl to work full time with her own dad,” says Disney Channel President Gary Marsh. “It’s even more unusual for a dad to work with his own daughter, as a colleague. As far as I could tell, they were the same dynamics I see now with my own 13-year-old daughter.”

“Hannah Montana” upended life for the Cyrus family, who were soon followed everywhere by paparazzi. “The good news is, I like people,” Cyrus says. “I fear more the day that nobody gives a s---. I think that’s a scarier reality, going out somewhere and nobody even caring.”


(Nathan Morgan/For The Washington Post)

Cyrus was more famous than he’d been in years, but his music career was flagging. During the 2000s and much of the ’10s, he tried everything: Patriotic albums. Christian albums. Heavy metal. “Dancing With the Stars.” He ditched Billy Ray and renamed himself Cyrus. He even grew his mullet back, hoping that audiences shared his nostalgia for that iconic, long-ago hairstyle. (They did not.)

By the time he and Von Tress finished work on “The SnakeDoctor Circus,” a concept album about the American condition that emphasized topical concerns such as opioid addiction, Cyrus thought he might never write another song. When “SnakeDoctor” was released in May, he says, “I figured that was probably it for me.”

But 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. For Cyrus, celebrity has seldom directly translated into record sales. “SnakeDoctor” did not chart, even at the fevered height of “Old Town Road” summer.

His success this go-round might be proximal, but it’s also easier to handle. After decades in which he worked himself to exhaustion onstage and on sets, straining his marriage and missing large portions of his kids’ childhoods, he can now do exactly as he pleases. He enjoys collaborations with younger artists and recently released the country-rock throwback song “Chevys and Fords,” a collaboration with singer Johnny McGuire. He has begun writing songs again. “I may just have peace of mind for the first time ever,” he says. “I feel like I can just lay my burden down.”

The one word Cyrus repeatedly uses to describe his life after “Old Town Road” is “magical.” “It’s just a beautiful, magical story that I look back on and I go, ‘I can’t imagine my life now without it,’ ” he says. “I never dreamed another one would come back around. I would’ve been fine. But now, looking back on it, this was my story.”