In late 2018, a kid from Georgia named Montero Lamar Hill spent $30 on a beat. He was living on his sister's floor, basically out of options, and used a Nine Inch Nails sample to record a weird, catchy track about horses and Maseratis. You know it as "Old Town Road." But before it was a 14-times Platinum juggernaut, it was a song that Billboard didn't want.
Then came the "Achy Breaky Heart" legend himself.
The pairing of Billy Ray Cyrus and Lil Nas X is honestly one of the weirdest, most effective pivot points in modern music history. It wasn't just a remix. It was a tactical strike against the Nashville establishment and a bizarrely wholesome friendship that actually changed how we define "country" music today.
The Billboard Rejection That Started Everything
Most people remember the song being a hit immediately. It wasn't. It blew up on TikTok first through the #YeehawChallenge. People would film themselves in regular clothes, then "snap" into full cowboy gear as the beat dropped. It was fun, it was viral, and it worked.
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By March 2019, the song actually debuted on the Billboard Hot Country Songs chart at number 19. It sat right there between Kelsea Ballerini and Morgan Wallen. But then, the "gatekeepers" stepped in. Billboard quietly removed the song, claiming it didn't "embrace enough elements of today’s country music."
Wait, what? Critics and fans were furious. People pointed out that white artists had been blending pop and country for years without getting booted. Lil Nas X was "extremely disappointed," but he had a plan. He’d actually tweeted months earlier, back in December 2018, that he wanted Billy Ray Cyrus on the song. Why? Because he grew up watching Hannah Montana.
How Billy Ray Actually Got Involved
It wasn't some corporate boardroom meeting. Tish Cyrus, Billy Ray’s wife, played him the song over coffee on March 16, 2019. Billy Ray loved it instantly. He felt it was "honest" and "humble."
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When Billboard threw the song off the charts, Billy Ray didn't just stay silent. He tweeted at Nas, saying that when Waylon Jennings got "outlawed" from the industry, he took it as a compliment. He told the kid: "Welcome to the club!"
When they finally got into the studio, Billy Ray was nervous. He did about ten takes. He tried a Johnny Cash voice. He tried different characters. At one point, the songwriter Jozzy told him, "Nas is imitating an artist like you—so you need to sound like you!" He finally let loose, added that iconic whistle at the end, and history was made.
Why Billy Ray Cyrus and Lil Nas X Still Matter
This collaboration did more than just break the record for the longest-running number-one single in Billboard history (19 weeks!). It forced a conversation about race and genre that the industry had been avoiding for decades.
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- The "Yeehaw Agenda": The song tapped into a larger cultural movement of Black Americans reclaiming cowboy culture.
- Genre-Bending is Now Standard: Look at the charts today. You’ve got Post Malone doing country and Beyoncé releasing Cowboy Carter. That door was kicked open by a $30 beat and a country veteran who refused to think "inside the box."
- The Diamond Factor: By October 2019, the remix was certified Diamond. It became the fastest song to ever reach 10 million units in the U.S.
Honestly, the most heartwarming part is the genuine respect between them. Billy Ray has called Nas a "light in this world." Nas, for his part, gave Billy Ray his first-ever CMA Award. Before this, Billy Ray hadn't had a hit of this magnitude since 1992.
What You Can Learn From This Viral Success
If you're a creator or just interested in how the "culture" moves, this story is a masterclass in staying authentic. Lil Nas X didn't change his sound to fit Nashville; he brought Nashville to him.
- Don't wait for permission. Nas self-released the song and marketed it himself on social media before a label ever touched it.
- Lean into the "No." When Billboard said it wasn't country, the remix with Billy Ray became a massive "yes" that the public couldn't ignore.
- Collaborate outside your bubble. The magic happened because two people from different worlds (and generations) decided to ignore the critics.
If you want to understand the current landscape of music, go back and listen to that remix. Notice the banjo (which is actually a sample of Trent Reznor). Listen to the trap drums. It’s a mess of styles that shouldn't work, but it’s basically the blueprint for how pop music functions in 2026.
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If you're digging into the history of these two, check out the official music video. It features cameos from Chris Rock and Diplo, and it’s basically a short film that perfectly captures the "fish out of water" vibe of the whole era. You might also want to look up the "Old Town Road" performance at the 2020 Grammys—it features everyone from Mason Ramsey (the yodeling kid) to BTS, proving just how far this "little song that could" actually went.