The story of "Old Town Road" is a wide-ranging one that spans several genres, continents and generations, but it begins and ends on the Internet. That's where the artist born Montero Hill decided to be a rapper in the first place (mostly to amuse his Twitter followers); that's where he bought a dusty-sounding, Nine Inch Nails-sampling beat from a Dutch producer named YoungKio for $30; that's where he released the two-minute, country-themed song (uploading it to SoundCloud, YouTube and iTunes) in December 2018; and of course, that's where he promoted it, feeding it into Twitter memes and generating fake buzz for it on Reddit and eventually getting it to catch on and go viral through TikTok, the short video-sharing service whose booming popularity and impact was starting to spill over into larger pop culture. By the time Lil Nas X was signed to Columbia Records in March 2019, he'd already laid all the groundwork necessary for it to become a No. 1 Hot 100 hit -- which it did, on the chart dated April 13 -- just as an unsigned 20-year-old screwing around online and trying to not get kicked out of his sister's house.
Viral hits were nothing new to pop music in the 2010s, from Rebecca Black and Psy becoming YouTube sensations at the decade's beginning, to Twitter and Instagram driving challenges that propelled "Black Beatles" and "In My Feelings" to chart-topping success in the decade's second half. But "Old Town Road" was something of a first in the way it was engineered from its very inception to be an Internet hit, actively pushed and promoted as such by its creator (who was then still far more practiced with producing viral content than he was with producing actual music) at every turn until social media had almost no choice but to let it take over. And while in past eras that naked self-promotion might've been gotten Lil Nas X branded as uncool or inauthentic, in 2019 -- when labels are less omnipotent than ever, and artists are more responsible for shaping their own destinies than ever -- it just made him a savvy DIY practitioner.
But there's a difference between getting a song to No. 1 and keeping it at No. 1, and Lil Nas X was hardly content with the former: Three days before the song was announced as the top song in the country, the song's first remix was revealed, with a well-known country artist as a special guest. Throwing out new remixes of a song in large part to goose stream and/or download totals and try to get a song over the chart hump was a well-established practice among artists nearing the Hot 100's top in the 2010s, often with an exciting or headline-grabbing guest artist in tow. But Lil Nas X's greatest inspiration came with the casting not of a particularly hip or timely country star as his supporting act, but '90s proto-viral star and Hannah Montana dad Billy Ray Cyrus. It was a left-field choice that felt authentic to the Lil Nas X experience, and indeed was something that he had effectively wished into existence by tweeting about it months earlier. And rather than feel tacked on -- as many guest remix contributions do -- Cyrus' verse fleshed out the song, made it feel complete.
Of course, Cyrus' contributions to "Old Town Road" were as much spiritual as they were practical. From nearly the beginning of the song's ascent, questions abounded about whether or not "Road" was, as Lil Nas X had initially tagged the song on SoundCloud and iTunes for largely marketing reasons, a country song. That discussion was largely ignited in March when Billboard made the call to remove the song from the Hot Country Songs chart, due in part to Lil Nas X's lack of recording history in the genre, and an unclear promotion or marketing plan by Columbia to country radio and streaming platforms. Questions were raised about who in the industry gets to decide what is and isn't a country song, about whether certain demographics were getting unfairly excluded in a genre largely dominated by white males, and about how genre should even be defined in an era where lines were getting blurrier every day. Regardless, Cyrus functioned as a sort of genre ambassador on the remix, both lending Lil Nas X his approval and helping him navigate the country space, almost rendering the entire argument over the original song a moot point.
Due to the combination of media exposure following the Billboard chart decision, and the higher plane of popularity the song reached following the Cyrus remix, "Old Town Road" reached a level of cultural omnipresence rarely seen in the 2010s. But rather than leave well enough alone with it and let the song continue to gather steam on its own, Lil Nas X and his team continued to push on it, recording several new remixes for the song that continued to keep it in the headlines, while garnering extra streams and downloads and to help keep it humming at No. 1 on the Hot 100. And when there wasn't a new remix to debut, the rapper still found new ways to keep the song in the mix -- a new video, the release of his accompanying 7 EP, a Twitter campaign -- and prevent its momentum from ever sagging. In the meantime, several of the biggest pop stars in the world (Taylor Swift, Shawn Mendes, Ed Sheeran) released new songs, but each proved unable to knock Lil Nas X from his perch at No. 1, as his run on the chart started to threaten the same 16-week history Luis Fonsi & Daddy Yankee's Justin Bieber-featuring "Despacito" had tied two years earlier.