Old Town Road: The Best Entertainment Case Study of 2019

Anthony McGuire
17 min readMay 8, 2019


Currently, the #1 song on the US Billboard Charts, the UK Single Charts, the Australian ARIA Charts and several other international charts is ‘Old Town Road’ by 20-year-old artist Lil Nas X (real name Montero Lamar Hill). The story behind the biggest song in the world right now is truly fascinating. If you understand why this song is significant, you will gain insight into how culture, media, and technology uniquely come together in the 21st century. It’s a window into the future of the entertainment industry and illuminates how the world is changing.

Through most of 2018, Lil Nas X was struggling financially, living with his sister in Atlanta and trying to become a rapper. He was creating his own music, uploading it to audio distribution platform Soundcloud, and then promoting his song through memes on social media. One of these songs was ‘Old Town Road.’ Lil Nas X bought the song’s beat from a 19-year-old producer from the Netherlands called YoungKio, off the website Beatstars. Lil Nas X paid around $40 for the beat.

YoungKio created the beat by remixing the original track ’34 Ghosts IV,’ which was written by industrial rock band Nine Inch Nails as part of the 2008 experimental album Ghosts I-IV. That album Ghosts I-IV was purposely released under a Creative Commons license, which meant that anyone was legally allowed to reuse, remix, and distribute the material so long as they provided credit to the writers. Now the combination of YoungKio, Trent Reznor (Nine Inch Nails) and Atticus Ross (Nine Inch Nails) are all listed on the song credits of ‘Old Town Road.’

In December 2018, Lil Nas X released ‘Old Town Road’ across several different platforms simultaneously — YouTube, Twitter, Soundcloud, Apple Music, and Spotify. On Soundcloud, he added tags to the song, including #Red Dead Redemption, #Country Trap, #Country Rap, and #Hick Hop. On YouTube, he uploaded a ‘music video’ for the song, consisting entirely of gameplay from the best-selling video game Red Dead Redemption 2.

Lil Nas X focused promoting the song through memes on different social media channels, especially Twitter. The most critical moment came when the #YeeHawChallenge was created and spread across popular short-form video mobile app Tik Tok. Users from around the world attempted the viral challenge by uploading videos of themselves drinking ‘yee yee juice’ and then transforming into a cowboy or cowgirl once the ‘Old Town Road’ beat dropped. Thanks at least in part to Tik Tok, the song became a huge hit and was climbing up the US Billboard Music charts in early 2019.

Given that the song was purposely created as a cross-genre combination of country music and rap music, ’Old Town Road’ was initially placed on the Billboard Hot Country charts. However, in mid-March Billboard removed ‘Old Town Road’ from the Country charts. Billboard’s public response justifying their decision included a statement that the song was “not embracing enough elements of today’s country music to chart in its current version.” As most digitally-savvy people realise, banning something on the internet usually results in the unintended consequence of giving that ‘banned’ content more publicity. This is also known as the Streisand Effect.

The chart removal sparked a huge debate within the music industry as to whether the song really is country, or whether such traditional genre classifications are even relevant in 2019. The public cried out in defense of Lil Nas X, with many considering Billboard’s actions the latest step in a racist ‘whitewashing’ of black artists within the country music genre, or at the very least a tone-deaf decision made by yet another out-of-touch gatekeeper of the music establishment. Celebrities and fellow artists voiced their support for Lil Nas X. One of those public supporters was country singer Billy Ray Cyrus, who tweeted,

“Been watching everything going on with OTR [Old Town Road]. When I got thrown off the charts, Waylon Jennings said to me “Take this as a compliment” means you’re doing something great! Only Outlaws are outlawed. Welcome to the club!”

What happened next? Lil Nas X reached out to Billy Ray Cyrus and they recorded a remix of ‘Old Town Road,’ with a new verse from Cyrus. The remix is now the #1 song on the overall Billboard charts, which is Billy Ray Cyrus’s very first Billboard #1 in his thirty year career as a country singer. Funnily enough, this is also the very first time Nine Inch Nails have had a song become a #1 Billboard Hit.

The song has taken on a life of its own, climbing music charts in countries all over the world. Athletes, singers, and all types of public entertainment figures are actively participating in the media uproar. Will Smith posted on Instagram referencing his role as a cowboy in 1999 film Wild Wild West, suggesting he would be the perfect person to star in the Old Town Road music video. Keith Urban, currently one of the biggest country singers in the world, recorded a banjo cover of the song. Ellen DeGeneres recorded herself dancing along to the song for the Ellen Show and Jimmy Fallon recorded a song parody for The Tonight Show. The NFL used ‘Old Town Road’ as opening music for the NFL Draft and numerous sports teams and individual athletes have uploaded content around the song. Even the main cast members of Avengers: Endgame all sang along to the song in a recent interview.

To top this off, Lil Nas X is now officially signed to Columbia Records and ‘Old Town Road’ has broken the U.S. record for single week streams of a song. Drake’s ‘In My Feelings’ was the previous record holder, streaming 116 million times in a single week last year. Old Town Road was streamed 143 million times in a single week.

The story behind Old Town Road is quite possibly the best case study ever to understand how technology, media, and culture now work in the 21st century. ‘Old Town Road’ isn’t just about music. It’s a look into the future of how technology is accelerating, categories are converging, and entertainment is internationalising.

Technology is Accelerating:

Lil Nas X is someone we might classify as Gen Z — a member of the generation of people born between the mid-1990s to the mid 2000s. It’s almost naturally implanted into the minds of Gen Z kids to understand, embrace, and reference internet culture better than any previous generation. Technology has changed the way that culture is communicated, particularly through social media. With more options to create and consume media, the amount of content available online is overwhelming. In order for you to cut through the noise, it’s critical for you to understand how to harness social media to build direct-to-fan relationships. Each step in the ascent of Old Town Road happened on social media, across different platforms.

Looking at Lil Nas X’s social media accounts is like receiving a masterclass in how social media should actually work when used well in capturing the pop culture zeitgeist. Lil Nas X mainly uses Twitter and Instagram to create feedback loops with his fans. He doesn’t just push out obvious promotional messages, but experiments with direct-to-fan interactions.

In some posts, he asks fans to build album art and publicly posts their fan submissions.

He releases previews of upcoming tracks, asking for creative feedback and adding hype. He reposts videos of fans dancing along to his songs from other social platforms, and reposts fan-created memes.

Fundamentally, Lil Nas X uses social media to do user testing on the ‘product’ that is his music and artist persona. He essentially sees social media as a tool for deep fan engagement, a mechanism to do free A/B testing, and a platform for 1-to-1 communication. By publicly recording what’s happening in his day-to-day life, in above average detail, he is authentically promoting all of his work. Reposting fan content also incentivises more fans to post, since he is making fans believe that there is a chance he might repost your content.

For example, here’s an instagram story I posted on ‘Old Town Road.’ I tagged Lil Nas X, but no response from him so far…I thought it was pretty clever.

Most of this sounds pretty straightforward, but Lil Nas X has truly succeeded in harnessing the power of social media. This is a rare feat. The vast majority of the world’s advertising agencies are packed with ‘hip’ creative directors who try to do the same thing and usually fail. Lil Nas X has been able to connect deeply with his fans. He doesn’t take himself too seriously and could serve as a case study for anyone who does marketing within the entertainment industry.

Pictured: Advertising Agency Executive Creative Director

One of the biggest songs of 2018 was ‘In My Feelings’ by Drake. Accompanying the song was the In My Feelings challenge, a specifically choreographed dance video that people would post on social media with the song playing in the background. These challenges are becoming a more common aspect of song releases and you can trace this back to the Ice Bucket Challenge of 2014.

The Ice Bucket Challenge was an internet meme that aimed to increase awareness about the disease ALS and encourage donations to medical research. People would upload videos of themselves dumping a bucket of ice water on their heads and then challenge their friends to do the same. Plenty of people got involved and celebrities of all types rushed to post their own videos. The Ice Bucket Challenge was itself a kind of digital media feedback loop. It was something you did as a result of someone challenging you, and it also required you to pass on the challenge to other people. You could describe the challenge as a real-life manifestation of a digital meme, a fun act or behaviour that people are encouraged to replicate, share, and add their own unique twist.

What is not so obvious is the fact that the technology required to upload high quality videos had been improving over the past few years and had only just got to the point where uploading a massive volume of videos like the Ice Bucket Challenge was possible. For many people, uploading their Ice Bucket Challenge (especially on Facebook) was the first video they had ever uploaded onto social media.

The ease of recording, editing, and uploading video content has gone through significant change. Because video technology today has advanced so much, you now have a huge proliferation of user-generated content. The breadth of video sub-categories available on the internet is impressive. From homemade makeup tutorials, to children unboxing presents, to videos of people reacting to hearing music, you now have brand new video categories that are continuing to diversify. The total amount of available video content is still increasing and accelerating in growth, as the technology itself progresses. Tik Tok is one of the latest manifestations of a new video platform and has played a huge role in helping Lil Nas X’s career.

Technology continues to progress to the point where we can now consume media and create digital feedback loops that previously weren’t possible. Technology creates brand new immersive opportunities for an artist to interact directly with their fans.

The artist Donald Glover (stage name Childish Gambino) created an augmented reality mobile app called Pharos, which is essentially a game that allows you to place an AR layer of ethereal artistic worlds on top of whatever your camera sees. You can unlock music, share your journey with friends through a multiplayer mode, and even interact with a virtual version of Childish Gambino. He recently performed at Coachella Music Festival where he released a film featuring him and Rihanna called Guava Island. He launched a new line of Adidas sneakers called ‘Donald Glover Presents’, using Apple AirDrop to give Coachella attendees a token they could present to redeem a free pair of sneakers, and he has created several one-minute short films across social media. This is in addition to writing, producing, and starring in his own TV series Atlanta, and hosting immersive concert experiences taking place in custom built domes.

Categories Are Converging:

With each successive generation, the lines between different genres of entertainment gets increasingly blurred. Lil Nas X understands this and it’s clear from following his social media accounts that he is proficient in several elements of pop culture — music, sports, memes, video games, anime, film. For young people like Lil Nas X, culture and technology are more intertwined than ever before. It’s one of the reasons why Billboard didn’t know how to react to Lil Nas X’s crossover music. In 2019, it’s less relevant than ever before to box things into clean, traditional categories.

For example, look at how Lil Nas X created a music video for ‘Old Town Road’ by using footage from the video game Red Dead Redemption 2. He is repurposing video game content for free and tapping into the already existing fanbase of the game — video game fans are likely also fans of music, sports, and other forms of entertainment. Lil Nas X is riding the pop culture wave of one of the best selling video games of 2018. Red Dead Redemption 2 grossed $725 million in its October 2018 opening weekend and the game’s storyline is essentially a cowboy western drama. The video game industry is also larger than the film industry and music industry combined in terms of annual revenue. So the fanbase of Red Dead Redemption is arguably just as powerful of a fanbase compared to the fanbases of any film or artist.

In February 2019, DJ Marshmello uploaded a digital version of himself into the video game Fortnite to play a digital concert, an event that 10.7 million people worldwide virtually attended. Could this open up a brand new revenue stream for all musicians to start performing concerts within video games? As I heard recently on the Bloomberg Business of Sports podcast, one of the hosts commented that for some kids, this Marshmello Fortnite concert might be the first ‘concert’ they would have ever ‘attended.’ Virtual concerts might be a brand new sub-category of the entertainment industry that combines music, video games, and sponsorship.

It’s increasingly relevant to connect to the videogame industry whenever you are doing something. Sports teams have been doing this more and more explicitly. The NBA partnered with Take-Two Interactive to launch their 2K esports league last year. The English Premier League has supported the creation of their very own ePremier League based on the game FIFA, and Formula One has also started their own F1 Esports Series. Former LA Lakers basketball player and three-time NBA champion Rick Fox actually owns an e-sports team called Echo Fox that competes in several different games such as League of Legends, Counter-Strike, and Street Fighter.

The NFL partnered with Fortnite in November 2018 to sell players wearable NFL team jerseys. CEO of Netflix, Reed Hastings, said in a January 2019 interview that Netflix competes more against Fortnite than HBO and other video streaming services. All this is happening because entertainment categories are converging.

Lil Nas X understands that he is not just competing against other rappers or even other musicians, he is competing for our attention. He is competing for the attention of fans all around the world, because there is more available content in our lives than ever before. Everything competes with everything. If you are running an ad at 8pm on Tuesday on a major TV channel, you are not just competing against other TV ads, you are competing against baby photos on their Facebook newsfeed, the mobile game they are planning, and all other hard-hitting content displayed on other apps they might be using.

Lil Nas X knows that intentionally crossing over into other entertainment categories is a winning strategy. He reposts each cross-industry reference and encourages more feedback. Here are some examples of people who have posted about ‘Old Town Road’: the University of Texas Football Team, the Boston Red Sox baseball team, the Dallas Stars ice hokey team, the Carolina Hurricanes ice hockey team, K-Pop band BTS, sports commentator Stephen Smith, and Ninja — one of the world’s most popular video game livestreamers.

All of this is ‘free media’ for Lil Nas X. Each time Jimmy Fallon, Ellen DeGeneres, or whomever else look to appeal to their own fans by commenting on the timely and relevant Old Town Road, they’ve created a sort of entertainment flywheel. They piggyback off Lil Nas X’s hit to increase their respective brands, and Lil Nas X also receives brand equity through association — another positive feedback loop.

The connection between sports and music is especially strong. Famous sports commentator Stephen A. Smith got involved by posting videos of himself doing his own version of the yeehaw challenge on Tik Tok and Twitter. During college basketball’s NCAA March Madness Championship Tournament, the Texas Tech basketball team was filmed celebrating to ‘Old Town Road’ in their locker room. Lil Nas X performed the song at a halftime show of the Atlanta Hawks. Dennis Rodman and Miley Cyrus have both actively commented on Lil Nas X’s social media channels. Former NBA star Shaquille O’Neil and former NFL star Ro Parrish, now both sports commentators, posted videos of themselves singing and dancing along to Old Town Road.

Another advantage to crossovers can also occur at a generational level. Let’s take Billy Ray Cyrus, the hero of the ‘Old Town Road’ remix. Older generations might remember Billy Ray Cyrus as a famous country singer. Younger generations might recognise him as the Dad on the TV show Hannah Montana, as the less famous father of Miley Cyrus.

You could say the same for Michael Strahan, who played a fifteen year career for the New York Giants. Since 2016, Strahan has been co-host of one of America’s biggest daytime talk shows. As time goes by, an increasing percentage of people in the world see Michael Strahan NOT as an athlete, but as a talk show host. Increasingly, people might start in one entertainment industry then move to another or consider themselves a cross-entertainment star by design.

The rapper Drake is well known for this. He has integrated himself so often into different sports that there is a specific sports meme called the ‘Drake Curse.’ The curse states that every time Drake poses for a picture with an athlete, that athlete usually ends up losing their next match. It has happened several times — UFC fighter Connor McGregor, the Paris Saint-Germain football team, and tennis player Serena Williams. FC Roma even tweeted about the ‘Drake Curse,’ jokingly posting that the football club has made it an official rule than no player is allowed to pose for a picture with Drake.

Memes are essentially crossover opportunities between music, sports, film, television, video games, and all other entertainment categories. Much like all the sports teams and celebrities who put their own spin on Old Town Road, you see similar meme reactions to grand pop culture moments like the latest Game of Thrones episode, exciting sports comebacks, or film awards ceremonies. These are all manifestations of an entertainment flywheel.

Entertainment is Internationalising:

Lil Nas X attributes a large part of his song’s success to the video app Tik Tok, which is owned by Chinese tech company Bytedance. In an official press release, Tik Tok wrote, “Lil Nas X’s success story highlights how talented artists are using Tik Tok to grow a fanbase and promote their music.” In the same release, Lil Nas X says, “Tik Tok helped me change my life. Tik Tok brought my song to several different audiences at once.”

Tik Tok plays a fascinating role in this story as a pioneering case of internationalisation. It’s the first time a Chinese tech company has played such a huge role in creating an American pop culture phenomenon. And I doubt it’s the last time we will see global culture influenced by Chinese tech and media. Tik Tok is part of the Chinese Bytedance group of apps, which is valued at around $75 billion and is the second most valuable privately held startup in the world, just behind Uber.

Bytedance acquired U.S.-based rival Musical.ly for $800 Million in November 2017 and then rebranded the app into Tik Tok, which is the Westernised version of their Chinese app Douyin. Musical.ly’s founders are also Chinese. Musical.ly was initially launched in both Chinese and American markets, but the app took off more rapidly in the U.S. than in China. Tik Tok has 500 million users worldwide, contributing to the total of 1 billion users across all platforms within the Bytedance group of apps and Tik Tok is the third most downloaded app in the world after Whatsapp and Facebook Messenger. Tik Tok was the most downloaded app in the world on the Apple App across the first half of 2018 and has deep user bases in several countries around Asia like India, Indonesia, and the Philippines.

I haven’t seen many Chinese companies have such a cultural impact on arts and entertainment. If Tik Tok/Bytedance can directly lead to a #1 Billboard song and one of the biggest songs in the world, are we only at the beginning of a trend towards global culture being driven by Asian tech?

The third highest grossing film of 2019 so far is the Wandering Earth, a Chinese sci-fi film based on a Chinese novel. Many Western film directors were approached to work on the film, but turned down the opportunity. The relatively unknown Chinese director who directed the Wandering Earth has now received a huge career boost.

Western sports teams, particularly European football teams, are scrambling to expand into Asia. The Premier League, Spanish La Liga, German Bundesliga, and Italian Serie A have been aggressively opening new offices, hosting new matches, and increasing brand activation across China, South East Asia, and India.

K-Pop stars have brought music, arts, and entertainment from Seoul to the hearts and minds of people all over the world. BTS is arguably the biggest boy band in the world, a group of Koreans who sing most of their lyrics in Korean yet sell out stadiums everywhere from Berlin to Los Angeles to Jakarta.

K-Pop boy band BTS at the 2019 Grammy Awards

I think this is a beautiful thing. The more that entertainment internationalises and converges, the more cultural barriers we will be able to overcome. And whether you like it or not, we live in a world where this is the reality of the 21st century.

While the legendary musician Elvis Presley definitely dabbled as an actor and model in the 1960s, he didn’t have to consider Twitch video game livestreaming, Twitter trolls, or growing Chinese fanbases. For a world famous athlete in 2019 like Cristiano Ronaldo, these additional techno-cultural factors is something he definitely has to consider.

You are not just competing against your category, you are competing against the complete options for entertainment in the world. Things are trending towards complexity and internationalisation in the world of entertainment and technology.

Any singer, athlete, or major entertainment brand can take advantage of these trends. The story of Lil Nas X is so special because he is the best case study of someone who has created an entertainment flywheel through these key concepts around technology, culture, and internationalisation.

For now, go listen to Old Town Road. It’s a tune.

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Anthony McGuire

Tech, Entertainment, Media, Emerging Markets. Ex-Facebook and Singularity University.