EXCLUSIVE: Cowboy Boot Shopping and the Real Meaning Behind "Old Town Road" With Lil Nas X

Plus Khalid, Brendon Urie, and more take the 'Yeehaw Challenge'

In-between trying on boots, we learned a lot about Lil Nas X and the earliest versions of his unstoppable song, "Old Town Road." From TikTok sensation to massive worldwide phenomenon, the 20-year-old stands at the center of the biggest hit of 2019, continuing his march into every corner of the culture before he has even released his debut album.

In the exclusive interview above, Lil Nas X talks about the time after dropping out of school and moving in with his sister, working on his music and starting with the seeds of what became "Old Town Road." In a house full of family, the clock was ticking for the singer to get it together and get out on his own, and early frustrations in the industry left him in a tough position. "This was during the time that I just had a song that was doing okay, then it slowed down" he explains. "I'm just kinda like, sad that, it's not what I thought it was gonna be, and my sister wants me gone and it looks like everything is closing in on me."

With pressure mounting, Lil Nas X considered stopping music to go back to school, but the discovery of a beat on YouTube quietly started the biggest success story of the year. "I started to write the song, and it started off as a loner, runaway cowboy" details Lil Nas X about the first phases of the hit. It would grow into something different, with the wild west imagery doubling for some of the trouble he was dealing with in his own life.

"Later on, through the month of me switching words in and melodies, and things out and stuff, I changed it so that the horse would be a symbol for not having much to work with and the Old Town Road be a path to success."

Something resonated, and the song caught fire on the social video sharing app. The Yeehaw Challenge was born with people posting clips of themselves dancing to the song Lil Nas X crafted in his sister's home. Eventually it would spill over into the mainstream, gaining so much steam that it began climbing the Country charts. Fueled by the controversy over its inclusion, "Old Town Road" got the injection it needed to become a monster. It's popularity has put it everywhere from wedding receptions to movie trailers, gaining co-signs from the biggest names in Country and Hip Hop along the way.

Somehow on the verge of reconsidering his path, Lil Nas X managed to create the most unifying song in years.

Everything that Lil Nas X has added to the viral hit in the time since has only furthered the reach and power of "Old Town Road." The video now has over 104 million views, and a remix featuring Billy Ray Cyrus has sent the song into another stratosphere. "I wanted Billy Ray on this song, since like two days after I made the song" he says. "I was nervous because I didn't know what he was gonna be like, but he's like this very humble guy, and he's just saying uplifting things the entire time."

What started with the Yeehaw Challenge has grown to challenge some of the biggest records in all of music. You can watch more from Lil Nas X in the exclusive interview above.

Before we wrapped up our boot-buying trip with the "Old Town Road" star, he issued a fresh challenge to all other artists. "I'm sending this hat on the road, I want to see who's gonna rock out to 'Old Town Road.'" We asked everyone from Brendon Urie, to Khalid, to Dan + Shay to give it a try. Even BTS told us how they rock with the singer. See our own Yeehaw Challenge below.