You know, when you plug a destination into a
GPS, it gives you, like, the fastest, most logical
route. Right, the approved path. Exactly. Stay
on the highway, take the exits everyone else
takes, follow the blue line, and if you dare
to veer off that pre -approved path, the system
just absolutely panics. It starts flashing, right?
Like, recalculating, recalculating. Yeah, demanding
that you turn around and get back on the main
road. And, um... You know, the music industry
operates like that exact same software. Oh, completely.
If you aren't hitting the standard milestones,
playing the expected sounds, and following the
traditional timeline, the executives assume you
must be lost. Welcome to the Deep Dive. I'm so
glad you're here with us today. Yeah, thanks
for tuning in. Today we're unpacking a massive
Wikipedia archive documenting the journey of
an artist... who basically spent his entire career
making the music industry's GPS screen recalculating.
I mean, he really did. We're talking about the
American rapper Jaron Benton. Yes. And our mission
today is to explore the career of a guy who actively
almost stubbornly defied regional expectations,
industry norms, and even the traditional timeline
of success. Just to build a deeply personal music
legacy on his own terms. Okay, let's unpack this.
We have to start at the beginning, down in Decatur,
Georgia. Right. Benton was born in 1981, which
places his formative years right in the thick
of the rising southern hip -hop dominance. And
that geographic context is just, well, it's crucial
to understanding his early struggles. Because
of the Atlanta sound, right? Exactly. In the
late 90s and early 2000s, Atlanta was really
cementing itself as the absolute center of gravity
for hip hop. There was a very specific down south
sound dominating the airwaves and the clubs.
It was largely bass heavy, bounce driven, and
highly localized. Like if you were there, you
played that sound. Right. If you were an up and
coming artist in that area, the expectation was
that you would slide seamlessly right into it.
to that sonic landscape. But Benton just didn't
fit that mold at all. No, not even close. He
gives this incredibly candid quote to XXL Magazine,
admitting that his early attempts at rapping
were, well, in his own words, kind of whack.
Which is hilarious to admit, but, you know, honest.
Yeah. He was going around Atlanta performing
at showcases, trying to build a name, but he
hit a massive wall. Mm -hmm. He noted it was
incredibly hard to gain traction because his
style just didn't fit that typical down south
vibe the local crowds were showing up for. And
looking at his influences, I mean, it makes perfect
sense why he felt like an alien in his own hometown.
Oh, for sure. His musical diet was completely
at odds with the local menu. His influence list
is wild. It reads like someone left a CD binder
open at a frat party in 1999 and just hit shuffle
on everything. It really does. He credits hip
hop legends, obviously. Outcast. Goody Mob, Wu
-Tang Clan, Eminem. Redmond, Dr. Dre. Yeah. But
then he cites deeply lyrical underground guys
like ELP, Rascass, and Chino XL. Which is already
pulling away from the mainstream club sound.
Right. And then he takes a hard left turn into
alternative and industrial rock. This is the
part that gets me. He brings up nine -inch nails,
deftones. and Marilyn Manson. Yeah. It's like
trying to sell a sci -fi thriller at a romance
novel convention. You might have undeniable talent
as a writer, your prose might be incredible,
but the local market you're standing in is absolutely
not looking for a genre -blending, dark, industrial
-tinged hip -hop sound. They want the club hits.
Exactly. What's fascinating here is how that
initial rejection acts as a crucible. How do
you mean? Well, When your immediate environment
doesn't validate you, you're forced into a corner.
You either conform to what the local scene wants,
which he clearly refused to do, or you look outward.
Yeah, you find your own lane. By embracing Marilyn
Manson and Wu Tang simultaneously, Benton was
cultivating a sound that couldn't be pigeonholed
by geography. He wasn't making it. Atlanta music,
you know. He was making Jaron Benton music. Exactly.
He isolated himself in his own specific tastes
to build something completely separate from the
local expectations. I want you, the listener,
to think about that for a moment. Think about
a time when you felt your own skills or your
passions or your weird niche interests just did
not align with your immediate environment. Oh,
that's a great point. Like, at a job. Right.
Maybe it was at a corporate job or in a specific
academic program. It feels incredibly frustrating
and isolating in the moment. But that friction
is often the exact thing that forces you to forge
a stronger, more unique identity. You stop trying
to blend in, and you start doubling down on what
makes you different. And that doubling down is
the defining characteristic of Benton throughout
the late 2000s. He didn't just give up. No. He
focused intensely on ref - finding that eccentric
craft, rather than trying to reverse engineer
a radio hit for the Atlanta market. Which leads
directly into his breakout period between 2009
and 2012. Right, because eventually his sound
catches the ear of the right people. He drops
his first official mixtape, produced entirely
by the Beat Gods, in 2009. Then in 2011, he teams
up with producer SMKA for a collaboration mixtape.
And the title of this project tells you everything
you need to know about his brand of humor and
his reliance on shock value. Oh, I know the one.
It was called Huffing Glue with Hasselhoff. That
title is just wild. Supported by the single Get
a Low to Me. But the real catalyst for his career
was a track called Skitzo. Yes, the music video
for Schitzo, that somehow crosses the radar of
the underground rapper Hopson. And Hopson was
huge in the underground scene then. Oh, yeah.
Hopson was building a massive independent following
of his own at the time. He watches the video,
immediately recognizes the raw talent and the
shared off -kilter sensibility, and he passes
it along to Dame Ritter. Who's the CEO of the
independent record label Funk Volume. Exactly.
A few months go by, Ritter reaches out, and by
May 2012, Hopson and Ritter Ritter officially
signed Benton to Funk Volume. Wow. He then drops
the mixtape Freebasing with Kevin Bacon the following
month. Another amazing title. Right. And he's
bringing in features from guys like Dizzy Wright,
Ritz, and Gangsta Boo. But what's wild is that
while all this underground momentum was building,
the mainstream establishment was actually watching
him closely. They definitely were. He wasn't
just getting calls from scrappy independent labels.
He was simultaneously being courted by absolute
industry heavyweights like Eric Cerny. and no
ID. Yeah, literal architects of hip -hop. And
they were offering him major label deals with
Def Jam recordings and Interscope Records, yet
he says no. He walked away. He walks away from
Def Jam to sign with Funk Volume. I have to push
back here. Wait, if Def Jam and Interscope come
knocking... Isn't a professional suicide to say
no and go with a relatively small indie label?
It looks entirely counterintuitive from the outside.
I mean, most people would kill for that deal.
Right. But if we connect this to the bigger picture,
it makes perfect strategic sense for an artist
like Benton. Break that down for us. You have
to understand the historic trade off in the music
industry. When you sign with a major label like
Def Jam or Interscope, you are getting access
to a massive global marketing machine. So radio,
billboards. Exactly. You get the big cash advances,
you get radio play, high budget videos, and mainstream
visibility. The rocket ship to the top. Yeah,
but the price of that rocket ship is almost always
your creative control and the actual ownership
of your master recordings. Ah, right. The fine
print. Major labels are notoriously risk -averse
because they are investing millions. Think back
to that GPS analogy. They want you on the highway.
A major label wants you on the highway. If Benton
went to Def Jam, the executives might listen
to his Marilyn Manson influences and his dark
humor and say, let's dial that back. Let's make
you sound more like what's currently charting
on the radio so we can recoup our investment
faster. They'd want to sand down his edges to
make him palpable for a mass audience. Independent
labels, on the other hand, offer a fraction of
the upfront money and marketing muscle. Sure.
But they give the artist a significantly larger
slice of the pie when it comes to royalties.
And more importantly, they let the artist steer
the ship creatively. Which he needed. Funk volume
wasn't going to tell him to change his sound.
They signed him specifically because of his eccentric
sound. You know, for everyone listening, think
about your own career choices. If you were offered
the prestigious corporate job, at the massive
firm, the one with the strict dress code, the
rigid hierarchy, but the huge name brand on your
resume, would you take it? A lot of people would.
Yeah. Or would you choose the chaotic startup
that pays less initially, but lets you completely
run your own department and build something in
your own image? And Benton chose the startup.
He did. But choosing independence comes with
a heavy physical and financial toll. I mean,
when you say no to Def Jam's money, you have
to fund your own existence? That explains the
insane touring schedule that follows. Oh, the
touring was brutal. In late 2012, he hits the
road internationally with Hopson, Dizzy Wright,
Swizz, and DJ Hoppa. They do 54 shows in 60 days
across the US, Europe, and Australia. 54 shows
in 60 days. That's almost a show every single
night with international travel. When you say
no to corporate money, that tour becomes the
physical cost of your independence. That is not
a glamorous pop star tour. That is blue collar,
sweat equity grinding to keep the lights on and
build a grassroots following city by city. And
that grueling grind. sets the stage for his debut
studio album in June 2013. My grandma's basement.
Right. And this album represents a pivot for
him. How so? He stated at the time that the project
had a different vibe. It was a lot more personal,
designed so people could learn who Jaron really
is beneath all that shock value. Getting past
the Huffing Lou persona. Exactly. He also featured
a more refined production sound because, you
know, he still had ambitions to be a household
name. He wasn't opposed to success. He just wanted
it on his turn. Right. He was proving he could
balance his eccentricities with accessibility,
but without a major label telling him how to
do it. And the personal touch completely worked.
My Grandma's Basement featured a diverse lineup
of guests, Aria the Rugged Man, Vinnie Paz, Hobson,
and it debuted at number 152 on the Billboard
200. Which is huge. And it hit number four on
the Billboard Hit Seekers chart. Right, and for
anyone unfamiliar, the Heat Seekers chart is
basically Billboard's spotlight for artists bubbling
just under the mainstream radar. Like a track
of a system for the next big thing. Exactly.
So for independent hip hop album in 2013, charting
on the Billboard 200 is a massive validation
of the DIY approach. The momentum snowballs rapidly
from there. He drops music videos for tracks
like Go Off and Life in the Jungle. He goes on
his first solo headlining tour, the Grandma's
Basement Tour, and jumps onto tours with Ritz,
Snowthi Product, Tech N9, and Freddie Gibbs.
He is just everywhere. It's a relentless pace
that culminates in a major industry moment in
2014. Here's where it gets really interesting.
Oh, the XXL -ist. Yes. Jaren Benton earns a spot
on the 2014 XXL freshman class. For context,
the XXL freshman list is essentially the hip
-hop industry's annual coronation of the next
big superstars. Getting on that magazine cover
is a career -making moment. Absolutely. But there
are two vital details here. First, Benton didn't
just get picked by the magazine editors in a
boardroom. He won the People's Champ fan vote.
Meaning his independent fans mobilized and essentially
forced him onto that list. Exactly. And second,
and this is the kicker, he was the oldest rapper
ever selected to the list. Wow. He was 32 years
old. Which is just unheard of. Youth is fiercely
fetishized in the music industry. Gatekeepers
are almost always looking for the 19 -year -old
prodigy they can mold and profit off of for the
next decade. Right. They want someone they can
steer. Breaking through at 32 is practically
impossible in that specific format. The real
takeaway here is that gatekeepers only have power
if they control your audience. Oh, that's a great
way to put it. Benton proved that if you own
your direct connection to the fans, you can completely
override ingrained industry prejudices like ageism.
The fans literally forced the industry to acknowledge
a 32 year old in a young man's game. It's like
winning a Best New Artist Award when you've actually
been working in the trenches for over 10 years.
Right, right. It's not overnight success. It
is fiercely delayed recognition. So he reaches
this incredible validating peak. He defied the
geography trap, he defied the major labels, he
defied his age, and then just as he reached at
the mountaintop, the ground completely falls
out from under him. Because the independent music
business is incredibly fragile. You don't have
a massive corporate safety net to catch you when
things go wrong, either personally or professionally.
Right. In early 2015, Benton releases his debut
EP titled Slow Motion. It charted on the Billboard
200, which is a great professional milestone.
But the story behind the title is just heartbreaking.
It was named after an old friend and fellow rapper
who had recently passed away. So he's dealing
with profound personal grief. Yeah. And then,
in 2016, his professional home vanishes. Funk
volume shuts down. Funk volume, the label he
helped build, suddenly shuts down due to internal
disputes among the founders. Suddenly, the independent
infrastructure that supported his rise, you know,
the people who booked those massive tours and
marketed those albums, it's completely gone.
Just wiped out. He's a free agent, but not by
choice. The machinery he relied on evaporated
overnight, leaving him entirely on his own. You
might think losing his label would be the end,
or at least force a massive multi -year hiatus.
A lot of artists would quit after that. But look
at the three -year period following the collapse.
It became an era of aggressive reinvention. He
didn't slow down at all. He hasn't just put out
another album. He builds his own enterprise.
Literally. He starts his own label, Benton Enterprises,
releasing Slow Motion Vol. 2 in 2016 as his first
project under the new banner. He's leveraging
the fierce fan base he built to fund his own
ecosystem. That works. In 2017, he drops his
third studio album, The Mink Coat Killa, intended
to be a tribute to the Wu -Tang Clan, referencing
his own Wu -Tang influenced moniker. He is constantly
working to ensure he doesn't lose an ounce of
momentum handling the distribution and marketing
himself. So he loses his label in 2016, but by
2018 he links up with a still Movin label and
guys like Dizzy Wright and Audio Push to create
an entire collaborative album called One Week
Notice. And it was called that because they literally
recorded the entire album in just seven days.
Which is insane. That's not just a guy making
music. That's an entrepreneur refusing to let
the machine dictate his timeline or his output.
And that relentless output, that sheer refusal
to quietly fade away, eventually attracts the
attention of the very establishment he initially
bypassed. Right. It comes full circle. In July
2018, Benton releases a single called Money Bag
with Jay Park and announces that his next collaborative
album, Yuck Fu, is going to be released under
Roc Nation. Yes, Jay -Z's Roc Nation. The ultimate
inner circle. And it's worth noting, just to
bring his discography completely up to date,
in 2022 he dropped a satirical track titled Nancy.
Right, featuring the rapper Samson. Yes. It's
a track centered around former U .S. House speaker
Nancy Pelosi. Now, as your guides today, we are
strictly mapping out his timeline. You want to
be very clear to you listening. We aren't taking
any political stances or endorsing the viewpoints
of the track or the politician. Exactly. We're
just impartially conveying the facts from the
source material. Right. But it's a factual piece
of his history that shows his continued reliance
on shock value and pushing boundaries. Looking
at that entire timeline, from the funk volume
collapse to the rock nation deal, you really
see the mechanics of survival in the modern music
landscape. So what does this all mean? How does
an indie artist with no corporate backing survive
losing his label in 2016 only to drop an album
recorded in a single week by 2018 and then suddenly
walk through the doors of hip -hop's biggest
empire at Roc Nation? This raises an important
question about what it actually means to be an
independent artist. Okay, tell me more. Benton's
entire career is a master class in adaptability.
Being independent isn't just a business model
for him. It's a survival skill. He went from
a scrappy indie label to becoming his own boss
at Benton Enterprises to signing with one of
the most prestigious entertainment companies
in the world. What he proved is that his core
value didn't lie in his corporate backing. His
value was his own brand. The audience wasn't
showing up for funk volume. They were showing
up for Jaren Benton. I want to challenge you,
the listener, to view your own setbacks through
that exact lens. When a project fails or a company
folds or a relationship ends, it's so easy to
see it as a definitive ending. Oh, absolutely.
But what if it's just a mandatory reinvention
phase? What if the skills you built during the
failure, the resilience, the networking, the
raw output, are the exact tools you need to build
your own enterprise? Benton didn't stop when
his local scene rejected him, he didn't stop
when the majors wanted to change his sound, and
he certainly didn't stop when his label dissolved.
He just kept recalculating the rap. Perfect callback
to the GPS. To summarize this deep dive, Jaren
Benton's journey is nothing short of relentless.
He started as an alienated kid in Decatur, Georgia,
listening to Marilyn Manson and Wu -Tang Clan
while everyone else was focused on the Down South
sound. He became an independent trailblazer who
gambled on himself, paid the brutal physical
cost of that independence on tour, and conquered
the XXL freshman list as the oldest inductee
at 32. He survived profound personal loss and
the sudden collapse of his record label. only
to build his own company and eventually find
himself walking through the doors of Jay -Z's
rock nation. It's an incredible narrative arc
of resilience, but you know, it leaves me with
one final, perhaps slightly provocative thought
for you to mull over today. Jaron Benton built
his entire identity on being the outsider. He
was the guy who rejected the major labels, the
guy who ignored the regional sound, the outlier
who forced his way in on his own terms. But what
happens to an artist's creative drive when their
specific brand of rebellion eventually gets co
-opted and rewarded by the establishment? Oh,
wow. When you sign with a behemoth like Roc Nation,
can you still be the ultimate outsider when you're
suddenly invited into the ultimate inner circle?
Oh man, that is a fantastic question to leave
off on. How do you keep the edge when you finally
won the war? Yeah. We'll leave you to think about
that one. Definitely something to think about.
Thank you so much for joining us on this deep
dive, navigating the off -road map of Jaren Benton's
career. We warmly invite you back for our next
exploration. Until then, keep questioning the
road.