August 24, 2025 • 13 mins
Welcome back to Hitmaker Chronicles' countdown of the Top 20 Songs of the Summer, as voted by the staff of Caloroga Shark Media! I'm your host, Garrett Fisher. Coming in at number 6, we're diving into Lil Nas X's genre-defying phenomenon "Old Town Road" featuring Billy Ray Cyrus — a track that broke the internet, challenged musical categorization, and spent a record-breaking 19 weeks at #1. We'll trace how a 20-year-old's $30 beat purchase became a cultural revolution while TikTok was reshaping music discovery and America was grappling with questions of authenticity and belonging. Saddle up — we're riding into the most unlikely country-rap crossover ever.
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Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
To become a premium subscriber (no ads and no feed drops) visit caloroga.com/plus. For Apple users, hit the banner on your Apple podcasts app which seays UNINTERRUPTED LISTENING. For Spotify or other players, visit caloroga.com/plus. You also get 25+ other shows on the network ad-free! Go to Caloroga.com for all our shows!
Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!
Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!
We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com
Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:03):
Kalaroga Shark Media Summer twenty nineteen.
Speaker 2 (00:13):
I'm Garrett Fisher, and the music industry was being completely
upended by platforms that most executives still didn't fully understand.
TikTok was transforming from a teen lip syncing app into
the most powerful music discovery engine on the planet, while
traditional gatekeepers, radio programmers, chart compilers, genre police were scrambling
(00:34):
to keep up with cultural shifts happening at Internet speed.
Into this chaos road Montero Lamar Hill, a twenty year
old from Georgia who would become Lil nas X with
a song that would challenge every assumption about genre authenticity
and how hits get made in the digital age, coming
in at number six on our countdown of the top
(00:55):
twenty songs of the summer, as voted by the staff
of Klaroga Shark Media. Lil nazak Us his Old Town
Road featuring Billy Ray Cyrus, represents the moment when social
media completely bypassed traditional music industry structures to create not
just a hit, but a cultural phenomenon that redefined what
American popular music could be. Before Lil Nazex was breaking
(01:17):
every record imaginable, he was Montero Lamar Hill growing up
in suburban Atlanta with dreams that had nothing to do
with music stardom. A college dropout who was living with
his sister and working temporary jobs, he had spent time
creating viral content on social media platforms, developing an intuitive
understanding of how internet culture worked and what made content spread.
(01:42):
His path to music was unconventional. He wasn't a trained musician,
didn't come from a musical family, and had no industry connections.
What he had was an encyclopedic knowledge of internet culture,
a natural instinct for viral content, and the kind of
fearless creativity that comes from having nothing to lose. When
he decided to try making music, he approached it with
(02:03):
the same experimental mindset he'd use for memes and social
media content. The creation of Old Town Road began when
Lil nas X purchased a beat for thirty dollars from
a producer called Young Kio, who had crafted it from
a sample of nine inch nails thirty four ghosts four.
This industrial rock foundation was an unconventional choice for what
(02:26):
would become a country rap fusion, but it provided the
perfect dark, atmospheric backdrop for Lil naz X's vision. Recording
the vocals in a makeshift home studio setup, Lil nas
X created something that defied easy categorization. The track combined
country imagery and themes with hip hop production and delivery,
(02:46):
creating a sound that was simultaneously familiar and completely new.
When he uploaded it to various streaming platforms in December
twenty eighteen, he probably had no idea he was about
to change popular music forever. The Soong's initial success came
through TikTok, where users began creating videos using the track
for everything from cowboy role playing to comedic sketches. This
(03:09):
organic growth on social media created momentum that eventually caught
the attention of streaming platforms and eventually traditional music industry gatekeepers.
So what made Old Town Road the perfect storm for
digital age music success?
Speaker 1 (03:23):
Let's break it down.
Speaker 2 (03:24):
Musically, Old Town Road succeeds by embracing, rather than hiding
its contradictions. The track builds on Young Kio's beat, which
combines the dark, atmospheric sample from nine Inch Nails with
trap influenced drums and sparse instrumentation that creates space for
lilns x's distinctive vocal delivery. The production is intentionally minimalist,
(03:45):
avoiding the overcrowded arrangements that might have obscured the song's
essential weirdness. The banjo sample from the nine Inch Nails
track provides an immediately recognizable country signifier, while the hip
hop drums and sparse arrange keep the track feeling contemporary
and fresh. What makes the production particularly effective is how
(04:06):
it doesn't try to reconcile its conflicting elements. Rather than
smoothing over the differences between country and hip hop, the
track celebrates the tension between them, creating something that sounds
both totally natural and completely impossible. The addition of Billy
Ray Cyrus on the remix elevated the track to new levels,
bringing legitimate country credibility while embracing, rather than rejecting the
(04:29):
song's hip hop elements. Cyrus's participation demonstrated that the country
establishment could evolve and embrace new sounds rather than simply
gatekeeping traditional forms. The simplicity of the arrangement also made
it perfect for social media use. The track was distinctive
enough to be immediately recognizable in short clips, while being
(04:50):
sparse enough not to overwhelm user generated content. The structure
of Old Town Road reflects its origins as a song
designed for Internet consumption rather than traditional race play. The
track gets to its hook immediately, with Lil nas X's
distinctive vocal delivery establishing the song's character from the opening lines.
The verses are conversational and meme ready, filled with quotable
(05:13):
phrases and imagery that work perfectly for social media content creation.
This wasn't accidental. Lil Nasax understood how internet culture worked
and crafted content that was designed to be remixed, referenced,
and recontextualized by users. The chorus is instantly memorable and
simple enough to be easily sung along with crucial for
(05:35):
a song that would become a participatory cultural phenomenon rather
than just a listening experience. When Billy Ray Cyrus joined
the remix, his contribution was seamlessly integrated while maintaining the
song's essential character. Rather than trying to make the song
more traditionally country, Cyrus embraced its hybrid nature and added
(05:56):
his own distinctive element to the mix. This structure, immediate hook,
memorable verses, sangable chorus was perfectly designed for the attention
economy of social media while still working as a complete
musical experience. The cultural impact of Oldtown Road extends far
beyond its musical qualities. The song became a lightning rod
(06:17):
for discussions about genre authenticity and cultural ownership in American music.
When Billboard initially removed the song from its country charts,
citing its insufficient country elements, it sparked debates about what
defines country music and who gets to make those decisions.
The controversy highlighted tensions that had existed in country music
(06:38):
for decades around race, authenticity and cultural gatekeeping. The fact
that a young black artist had created one of the
most successful country influenced songs in years forced uncomfortable conversations
about the genre's relationship with its own history and demographics.
Lil nas X's response to these controversies, truiting Billy ray
(07:00):
Cyrus for a remix and eventually coming out as gay
while at the peak of his success, demonstrated a fearless
approach to authenticity that resonated with younger audiences while challenging
traditional industry expectations. The song's success also represented a complete
victory for social media driven music discovery over traditional industry gatekeeping.
(07:22):
By the time radio and streaming services caught up with
Old Town Roads popularity, it was already too big to
ignore or contain. What truly makes Old Town Roads special
is Lil Nazex's charismatic performance and his complete commitment to
the song's bizarre premise. His vocal delivery combines confidence with humor,
creating a character that's both larger than life.
Speaker 1 (07:44):
And completely relatable.
Speaker 2 (07:46):
The way he handles the song's country imagery, embracing it
without irony while also clearly having fun with it, demonstrates
a sophisticated understanding of how cultural references can be both
sincere and playful simultaneously. When Billy Ray Cyrus joined the remix,
the chemistry between the two generations of performers created something special.
(08:07):
Cyrus brought his experience and credibility while embracing Lil Nazex's
youthful energy and Internet native sensibility. The overall performance has
an infectious joy that made it impossible to resist, even
for listeners who might have been skeptical of its genre
blending approach.
Speaker 1 (08:24):
More in a Moment. Old Town Road.
Speaker 2 (08:37):
Was initially released in December twenty eighteen, but gained momentum
throughout early twenty nineteen, eventually reaching number one on the
Billboard Hot one hundred in April. The Billy Ray Cyrus
remix helped it stay at the top for an unprecedented
nineteen weeks, breaking the record previously held by Mariah Carey
and Boys to Men's One Sweet Day. The song's success
(08:59):
coincided with TikTok's emergence as a major force in American culture,
demonstrating the platform's power to drive mainstream success while creating
new models for how.
Speaker 1 (09:08):
Music could spread and evolve.
Speaker 2 (09:11):
To fully appreciate the impact of Old Town Road, we
need to examine the cultural landscape of summer twenty nineteen,
a season when social media was fundamentally reshaping entertainment while
America was grappling with questions of identity, authenticity, and cultural ownership.
The summer movie season featured Avengers End Game, which became
(09:31):
the highest grossing film of all time, while Toy Story
four provided emotional conclusion to a beloved franchise. Once upon
a Time in Hollywood offered Quentin Tarantino's nostalgic vision of
nineteen sixties Los Angeles, reflecting broader cultural fascination with examining
the past. Musically, twenty nineteen was marked by the continued
(09:53):
dominance of streaming and playliss culture, with artists like Ariana Grande,
Post Malone and Billy I Eilish achieving massive success through
directfan engagement and social media presence. The year also saw
increased attention to mental health and authenticity and pop culture,
themes that would become central to Lil nas X's public persona.
(10:15):
Technology continued evolving rapidly, with TikTok growing from a niche
app to a global phenomenon that was reshaping everything from
music discovery to political discourse. The platform's algorithm driven content
distribution created new possibilities for viral success while challenging traditional
media gatekeeping. This was the landscape in which Oldtown Road
(10:38):
achieved its remarkable success, a moment when traditional boundaries were
being questioned and new forms of cultural expression were finding
massive audiences through digital platforms. For Lil Nass personally, Old
Town Road represented not just commercial success, but cultural impact
that extended far beyond music. His decision to come out
(11:00):
publicly while at the height of his fame was groundbreaking
for both hip hop and country music. Genres that had
traditionally been less welcoming to LGBTQ plus artists. The song's
success also demonstrated the power of social media to create
new models of artistic success, showing how artists could build
massive audiences without traditional industry support or radio promotion. Looking
(11:24):
back on Oldtown Road today, it represents a watershed moment
when internet culture fully merged with mainstream music, creating something
that was both completely of its moment and influential for
the future. What makes Oldtown Road the quintessential social media
era summer anthem is its perfect understanding of how content
(11:45):
spreads and evolves in digital culture. The song wasn't just
consumed passively. It became a template for creative expression, with
countless users creating their own versions and interpretations. The track's
success also challenged traditional notion of musical authenticity, proving that
genre boundaries were more fluid than industry gatekeepers wanted to admit,
(12:06):
and that audiences were ready for artists who embraced rather
than hid their contradictions. So, as we continue our countdown
of the top twenty songs of the Summer, at number six,
Oldtown Road reminds us that sometimes the most Impactful music
comes from the most unexpected places, created by artists who
understand their cultural moment better than the industries trying to
(12:28):
contain them. Because Oldtown Road isn't just a song, It's
a cultural revolution disguised as a meme, a challenge to
musical gatekeeping, and proof that in the digital age, authenticity
matters more than adherence to traditional categories. Four years later,
it remains the perfect example of how internet culture can
create genuinely transformative art, which is why it deserves its
(12:52):
place in our Summer song's pantheon. This is Garrett Fischer
for hit Maker Chronicles counting down the top twenty songs
of the summer, as voted by the staff of Calaroga
Shark Media. Keep that digital frontier spirit alive and join
me next week as we continue our countdown with number five.
Kalaroga Shark Media Summer twenty nineteen.
Speaker 2 (00:13):
I'm Garrett Fisher, and the music industry was being completely
upended by platforms that most executives still didn't fully understand.
TikTok was transforming from a teen lip syncing app into
the most powerful music discovery engine on the planet, while
traditional gatekeepers, radio programmers, chart compilers, genre police were scrambling
(00:34):
to keep up with cultural shifts happening at Internet speed.
Into this chaos road Montero Lamar Hill, a twenty year
old from Georgia who would become Lil nas X with
a song that would challenge every assumption about genre authenticity
and how hits get made in the digital age, coming
in at number six on our countdown of the top
(00:55):
twenty songs of the summer, as voted by the staff
of Klaroga Shark Media. Lil nazak Us his Old Town
Road featuring Billy Ray Cyrus, represents the moment when social
media completely bypassed traditional music industry structures to create not
just a hit, but a cultural phenomenon that redefined what
American popular music could be. Before Lil Nazex was breaking
(01:17):
every record imaginable, he was Montero Lamar Hill growing up
in suburban Atlanta with dreams that had nothing to do
with music stardom. A college dropout who was living with
his sister and working temporary jobs, he had spent time
creating viral content on social media platforms, developing an intuitive
understanding of how internet culture worked and what made content spread.
(01:42):
His path to music was unconventional. He wasn't a trained musician,
didn't come from a musical family, and had no industry connections.
What he had was an encyclopedic knowledge of internet culture,
a natural instinct for viral content, and the kind of
fearless creativity that comes from having nothing to lose. When
he decided to try making music, he approached it with
(02:03):
the same experimental mindset he'd use for memes and social
media content. The creation of Old Town Road began when
Lil nas X purchased a beat for thirty dollars from
a producer called Young Kio, who had crafted it from
a sample of nine inch nails thirty four ghosts four.
This industrial rock foundation was an unconventional choice for what
(02:26):
would become a country rap fusion, but it provided the
perfect dark, atmospheric backdrop for Lil naz X's vision. Recording
the vocals in a makeshift home studio setup, Lil nas
X created something that defied easy categorization. The track combined
country imagery and themes with hip hop production and delivery,
(02:46):
creating a sound that was simultaneously familiar and completely new.
When he uploaded it to various streaming platforms in December
twenty eighteen, he probably had no idea he was about
to change popular music forever. The Soong's initial success came
through TikTok, where users began creating videos using the track
for everything from cowboy role playing to comedic sketches. This
(03:09):
organic growth on social media created momentum that eventually caught
the attention of streaming platforms and eventually traditional music industry gatekeepers.
So what made Old Town Road the perfect storm for
digital age music success?
Speaker 1 (03:23):
Let's break it down.
Speaker 2 (03:24):
Musically, Old Town Road succeeds by embracing, rather than hiding
its contradictions. The track builds on Young Kio's beat, which
combines the dark, atmospheric sample from nine Inch Nails with
trap influenced drums and sparse instrumentation that creates space for
lilns x's distinctive vocal delivery. The production is intentionally minimalist,
(03:45):
avoiding the overcrowded arrangements that might have obscured the song's
essential weirdness. The banjo sample from the nine Inch Nails
track provides an immediately recognizable country signifier, while the hip
hop drums and sparse arrange keep the track feeling contemporary
and fresh. What makes the production particularly effective is how
(04:06):
it doesn't try to reconcile its conflicting elements. Rather than
smoothing over the differences between country and hip hop, the
track celebrates the tension between them, creating something that sounds
both totally natural and completely impossible. The addition of Billy
Ray Cyrus on the remix elevated the track to new levels,
bringing legitimate country credibility while embracing, rather than rejecting the
(04:29):
song's hip hop elements. Cyrus's participation demonstrated that the country
establishment could evolve and embrace new sounds rather than simply
gatekeeping traditional forms. The simplicity of the arrangement also made
it perfect for social media use. The track was distinctive
enough to be immediately recognizable in short clips, while being
(04:50):
sparse enough not to overwhelm user generated content. The structure
of Old Town Road reflects its origins as a song
designed for Internet consumption rather than traditional race play. The
track gets to its hook immediately, with Lil nas X's
distinctive vocal delivery establishing the song's character from the opening lines.
The verses are conversational and meme ready, filled with quotable
(05:13):
phrases and imagery that work perfectly for social media content creation.
This wasn't accidental. Lil Nasax understood how internet culture worked
and crafted content that was designed to be remixed, referenced,
and recontextualized by users. The chorus is instantly memorable and
simple enough to be easily sung along with crucial for
(05:35):
a song that would become a participatory cultural phenomenon rather
than just a listening experience. When Billy Ray Cyrus joined
the remix, his contribution was seamlessly integrated while maintaining the
song's essential character. Rather than trying to make the song
more traditionally country, Cyrus embraced its hybrid nature and added
(05:56):
his own distinctive element to the mix. This structure, immediate hook,
memorable verses, sangable chorus was perfectly designed for the attention
economy of social media while still working as a complete
musical experience. The cultural impact of Oldtown Road extends far
beyond its musical qualities. The song became a lightning rod
(06:17):
for discussions about genre authenticity and cultural ownership in American music.
When Billboard initially removed the song from its country charts,
citing its insufficient country elements, it sparked debates about what
defines country music and who gets to make those decisions.
The controversy highlighted tensions that had existed in country music
(06:38):
for decades around race, authenticity and cultural gatekeeping. The fact
that a young black artist had created one of the
most successful country influenced songs in years forced uncomfortable conversations
about the genre's relationship with its own history and demographics.
Lil nas X's response to these controversies, truiting Billy ray
(07:00):
Cyrus for a remix and eventually coming out as gay
while at the peak of his success, demonstrated a fearless
approach to authenticity that resonated with younger audiences while challenging
traditional industry expectations. The song's success also represented a complete
victory for social media driven music discovery over traditional industry gatekeeping.
(07:22):
By the time radio and streaming services caught up with
Old Town Roads popularity, it was already too big to
ignore or contain. What truly makes Old Town Roads special
is Lil Nazex's charismatic performance and his complete commitment to
the song's bizarre premise. His vocal delivery combines confidence with humor,
creating a character that's both larger than life.
Speaker 1 (07:44):
And completely relatable.
Speaker 2 (07:46):
The way he handles the song's country imagery, embracing it
without irony while also clearly having fun with it, demonstrates
a sophisticated understanding of how cultural references can be both
sincere and playful simultaneously. When Billy Ray Cyrus joined the remix,
the chemistry between the two generations of performers created something special.
(08:07):
Cyrus brought his experience and credibility while embracing Lil Nazex's
youthful energy and Internet native sensibility. The overall performance has
an infectious joy that made it impossible to resist, even
for listeners who might have been skeptical of its genre
blending approach.
Speaker 1 (08:24):
More in a Moment. Old Town Road.
Speaker 2 (08:37):
Was initially released in December twenty eighteen, but gained momentum
throughout early twenty nineteen, eventually reaching number one on the
Billboard Hot one hundred in April. The Billy Ray Cyrus
remix helped it stay at the top for an unprecedented
nineteen weeks, breaking the record previously held by Mariah Carey
and Boys to Men's One Sweet Day. The song's success
(08:59):
coincided with TikTok's emergence as a major force in American culture,
demonstrating the platform's power to drive mainstream success while creating
new models for how.
Speaker 1 (09:08):
Music could spread and evolve.
Speaker 2 (09:11):
To fully appreciate the impact of Old Town Road, we
need to examine the cultural landscape of summer twenty nineteen,
a season when social media was fundamentally reshaping entertainment while
America was grappling with questions of identity, authenticity, and cultural ownership.
The summer movie season featured Avengers End Game, which became
(09:31):
the highest grossing film of all time, while Toy Story
four provided emotional conclusion to a beloved franchise. Once upon
a Time in Hollywood offered Quentin Tarantino's nostalgic vision of
nineteen sixties Los Angeles, reflecting broader cultural fascination with examining
the past. Musically, twenty nineteen was marked by the continued
(09:53):
dominance of streaming and playliss culture, with artists like Ariana Grande,
Post Malone and Billy I Eilish achieving massive success through
directfan engagement and social media presence. The year also saw
increased attention to mental health and authenticity and pop culture,
themes that would become central to Lil nas X's public persona.
(10:15):
Technology continued evolving rapidly, with TikTok growing from a niche
app to a global phenomenon that was reshaping everything from
music discovery to political discourse. The platform's algorithm driven content
distribution created new possibilities for viral success while challenging traditional
media gatekeeping. This was the landscape in which Oldtown Road
(10:38):
achieved its remarkable success, a moment when traditional boundaries were
being questioned and new forms of cultural expression were finding
massive audiences through digital platforms. For Lil Nass personally, Old
Town Road represented not just commercial success, but cultural impact
that extended far beyond music. His decision to come out
(11:00):
publicly while at the height of his fame was groundbreaking
for both hip hop and country music. Genres that had
traditionally been less welcoming to LGBTQ plus artists. The song's
success also demonstrated the power of social media to create
new models of artistic success, showing how artists could build
massive audiences without traditional industry support or radio promotion. Looking
(11:24):
back on Oldtown Road today, it represents a watershed moment
when internet culture fully merged with mainstream music, creating something
that was both completely of its moment and influential for
the future. What makes Oldtown Road the quintessential social media
era summer anthem is its perfect understanding of how content
(11:45):
spreads and evolves in digital culture. The song wasn't just
consumed passively. It became a template for creative expression, with
countless users creating their own versions and interpretations. The track's
success also challenged traditional notion of musical authenticity, proving that
genre boundaries were more fluid than industry gatekeepers wanted to admit,
(12:06):
and that audiences were ready for artists who embraced rather
than hid their contradictions. So, as we continue our countdown
of the top twenty songs of the Summer, at number six,
Oldtown Road reminds us that sometimes the most Impactful music
comes from the most unexpected places, created by artists who
understand their cultural moment better than the industries trying to
(12:28):
contain them. Because Oldtown Road isn't just a song, It's
a cultural revolution disguised as a meme, a challenge to
musical gatekeeping, and proof that in the digital age, authenticity
matters more than adherence to traditional categories. Four years later,
it remains the perfect example of how internet culture can
create genuinely transformative art, which is why it deserves its
(12:52):
place in our Summer song's pantheon. This is Garrett Fischer
for hit Maker Chronicles counting down the top twenty songs
of the summer, as voted by the staff of Calaroga
Shark Media. Keep that digital frontier spirit alive and join
me next week as we continue our countdown with number five.
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