Welcome to the Deep Dive. We take your sources,
boil them down, get right to the good stuff,
the things you really need to know. That's the
plan. And today, well today we're looking at
someone with, let's call it a pretty stark dual
identity. Maybe one of the most incredible ones
in entertainment right now. Oh yeah, definitely.
You've got this guy who's on one hand an Emmy
-nominated Hollywood comedy writer. Right. Very
polished world. Right, writing for big shows.
Exactly. And then on the other hand, he's this...
outrageously successful, super explicit outlaw
country musician. Just unbelievably filthy. But
people love it. It's this huge contrast. So we're
talking about Benjamin Isaac Hoffman. That's
him. The writer, comedian, producer. And then
there's Wheeler Walker Jr. The alter ego. The
uncensored country star. So our mission today
really is to unpack this. How does one person
do both? We need to look at his chart success,
which is kind of unique. Definitely unique. And
understand what he's trying to do with this character.
Is it just satire? Is he genuinely trying to
critique modern country music? Maybe even save
it in his own weird way? Yeah, it's a big question.
We've got some great sources here that really
lay out this wild journey. And they start right
at the beginning. Benjamin Isaac Hoffman, born
in Lexington, Kentucky. And here's a fun fact
right off the bat. Connects him to music early
on. His younger brother is Scott Hoffman. Ah,
baby daddy. Exactly. Baby daddy. The bassist
for the Scissor Sisters. So, you know, music's
in the family. It's in the DNA, yeah. Yeah. But
the way Den went about it is radically different.
Radically different is putting it mildly. So
how does someone with these, like, legit... mainstream
comedy chops become one of the most streamed
country artists on the planet without, and this
is key, without any FM radio play. Zero. It's
incredible. And that's where we have to start,
right? We need to be that foundation. Understand
the Ben Hoffman side first. The professional
side. Because Wheeler Walker Jr., he wasn't just
some random idea. He was, well, he was engineered
by someone who really knew what they were doing.
Okay, let's dig into that. The groundwork. Because
before, you know, Redneck shit the album, Ben
Hoffman was pretty deep in the Hollywood comedy
scene. And not just as a stand up, but as a writer,
a producer. He understands how TV gets made.
Oh, absolutely. His skills go way beyond just
telling jokes. It's structure, production, timing,
the whole package. He wasn't just trying to get
on shows. He was creating them. Right. And that
foundation is, like you said, solid. He built
it up over years. Exceptionally solid. I mean,
the first big thing was his own show, right?
The band show. On Comedy Central, yeah, 2013.
Creator, host, executive producer, running the
whole thing. That's major experience, even if
it only ran for one season. Building a show from
scratch on a big network like that. Exactly.
It's the proving ground. And crucially, our sources
point out, that's where Wheeler Walker Jr. actually
first showed up. as a character on that show.
Ah, okay. So the seed was planted right there
on his own platform. Incubated, yeah. But then
look at his writing credits. They show incredible
range. He wrote for a sports show with Norm MacDonald.
Norm MacDonald? That's a very specific kind of
comedy. Oh, yeah. Super dry, cynical, really
subversive. You've got to master that deadpan,
that sustained character thing, to work with
Norm. And that skill, that sustained character
work. That's pure Wheeler Walker Jr., right?
Keeping that persona going for years. Absolutely
vital. But then look at the contrast. He goes
from that super niche cult comedy to the late,
late show with James Corden, peak mainstream
network TV. Wow. Okay. Total shift. He was a
staff writer. They wrote like 38 episodes between
2015, 2016. Think about that adjustment. Massive
adjustment. You're going from Norm Macdonald's
world to writing, you know, clean, fast turnaround
stuff for a huge, broad audience. It shows he
can adapt his voice, meet the technical demands.
He knows how different writers rooms work. And
then there's animation, too. He wrote for Archer.
Yep. Southbound and down. Vision Quest. Highly
acclaimed show. Animation requires serious world
building. And it's not just sitcoms. He's got
these big live event credits, too. MTV Video
Music Awards, the Comedy Central roast of James
Franco. Writing for a roast. I mean, that's about
finding the absolute sharpest, most offensive
joke possible. But making it work live, structuring
it right. Exactly. It's about calibrating offense
for impact. He clearly understands that. So he's
got this mastery of different comedic styles,
subtle satire, mass appeal, brutal jokes. And
he kept acting and producing, too. Little part's
a new girl. Arrested development. Remember, FBI
guy, hashtag one. Ha! Yes. Classic. And more
recently, he created and ran hoops for Netflix.
Animated show. Right. The basketball coach one.
Canceled after a season, but still, he was the
showrunner. Yeah. Building another world. So
you put it all together, you've got this Emmy
-nominated producer, a guy who knows Hollywood
inside and out. Contacts, funding know -how,
deep understanding of media. And that's the guy
who decides to become Wheeler Walker Jr. It's
fascinating how that professional stability actually
fueled the rebellion. Well, it's more than just
fuel. It's the engine and the toolkit. His comedy
background gave him, first, production value.
That first Wheeler album wasn't some cheap demo.
Dave Cobb produced it. Huge Nashville name. Right.
Instant credibility. Second, he understands narrative.
Character consistency. Keeping Wheeler believable,
or at least consistently outrageous, over years
and albums. And third, maybe the most important
thing, he knew how to execute the joke. The big
high concept joke. Which is? Wheeler Walker Jr.
isn't just a dirty singer. He's a long form multimedia
critique. of the entire country music industry,
cleverly disguised as the crudest guy imaginable.
Okay, okay. So the TV background gave him the
skills to pull off this massive, sustained, satirical
performance piece. Exactly. He knew how to structure
it, how to package it, how to make it go viral,
how to make it profitable. He wasn't just mad
at Nashville. He was building a product, a very
specific, very provocative product. Designed
to push buttons and make money doing it. And
that product, that glorious, filthy product.
It started as that skit on The Ben Show. Back
in 2013, yeah. Performing the song that kind
of became his calling card. Eating pussy, kicking
ass. Yeah, sets the tone immediately, doesn't
it? Understatement of the year. But, you know,
behind the shock value, there's real motivation.
Huffman's pretty open about it. He uses Wheeler
to vent his frustration with modern country.
Specifically bro country. Right, that was the
big target. Exactly. We should probably define
that quickly for anyone who missed that particular...
Yeah. Brig. Good idea. So bro country. Huge in
the 2010s. Think like heavy pop and hip hop beats,
drum loops. This is the sizers. Yeah. And the
lyrics. Mostly about trucks, beer, tailgates,
girls in cutoff shorts. Pretty repetitive stuff.
Very formulaic. And a lot of country purists
saw it as, well, sanitized, commercialized, lacking
the storytelling heart of traditional country.
Okay. So Wheeler Walker Jr. is the reaction to
that. He's the raw, unfiltered antidote. His
whole backstory is built on that critique. He's
the unsigned Nashville guy who was too crude
for radio. Right, the guy they wouldn't play.
And his mission, he says, is to bring back that
classic outlaw country vibe, but cranked way
past 11. Songs so raw that get you kicked off
the Opry stage instantly. So he's fighting the
mainstream polish with extreme crudeness. But
here's the twist. He's anti -establishment, but
he uses the new establishment about... The internet,
streaming, social media to build this audience.
Proving there's still a market for that uncensored
stuff, just not through the old channels. Precisely.
And this is where the Hollywood producer brain
comes back in. The launch of the first album,
Redneck Shit, in 2016. Yeah. Super strategic.
We mentioned Dave Cobb producing, which gives
it musical legitimacy. The launch. Yeah. The
very first place you could stream it. Where was
it? Pornhub. Pause. Seriously. Pornhub. Yep.
Not just some random music site. Porn hub. Think
about that decision. OK, that's that's a statement.
It's more than just shark value. Like you said,
it's marketing genius in a really weird way.
It immediately screams the normal rules do not
apply here. Forget radio edits. Forget clean
marketing. This is something else entirely deliberate,
memorable, provocative. And he put his own money
behind it, too. Right. You mentioned that earlier.
Yeah. And this quote from Hoffman really drives
it home. He said, I took my fucking life savings.
And I gave it all to Dave and said, let's make
the album without any fucking record company
telling me what to do. Wow. Okay. So he literally
bought his freedom. Bought his own uncensored
voice. If a label had funded it, they would demand
it changes. It would kill the whole joke, the
whole premise. Using his mainstream earnings
to fund his anti -mainstream persona, the irony
is thick. It's layers upon layers. And this whole
package, this complex character, he gets compared
to some interesting figures. Like who? Well,
sources mention Chinga Chavin. Okay, the raunchy
musical comedy guy. Right. Yeah. Then Andy Kaufman.
For the performance art aspect. Never breaking
character. Exactly. Always staying in the joke.
And David Allen Coe. The original outlaw. The
genuine, gritty, controversial country figure.
So Wheeler's like a blend of all three. Yeah.
The musical skill, the commitment to the bit,
and that hardcore rebel attitude. It's smart,
because just being offensive gets old quick.
But if the music's actually good, and the performance
is committed... Then the satire works. And it
clearly did work, commercially speaking. Which
is kind of the next big surprise. Yeah, let's
talk about the charts, because this is where
it gets really undeniable. The industry had to
notice. This wasn't just an internet joke. Not
at all. That first album, Redneck Shit 2016,
it sold 5 ,900 copies in its first week, which
is decent for an indie release. But where did
it chart? Number nine on the Billboard Hot Country
Albums chart. Number nine. An independently funded,
completely explicit album in the top 10 country
chart. Unheard of, basically. Especially back
then. But wait, there's more. Go on. It also
debuted at number one on the Billboard Top Comedy
Albums chart. At the same time. Whoa! Okay. Country
and comedy charts top 10 simultaneously. Yep.
The sources say it was the first album in over
a decade to pull that off. It proved he wasn't
just one thing. He hit both audiences perfectly.
That's incredible. And it wasn't a fluke, right?
The second album. Old Wheeler, 2017. He did it
again. Debuted number 10 on country, number one
on comedy again. Stayed at number one comedy
for three weeks straight. And sold even more
first week, right? Like 700, 800 copies. Yeah.
Established a pattern. This wasn't fading away.
He had a real dedicated audience. And the key
thing, we have to keep stressing this. Zero FM
radio support. Absolutely none. This was all
streaming, social media buzz, digital sales.
It basically proved you could build a successful
country music career completely outside the Nashville
machine. If the content was strong enough and
authentic enough, even crudely authentic. The
audience was there waiting for something raw,
something uncensored. He tapped right into it.
So the music press, they had to react, right?
They couldn't ignore. Top ten albums. Nope. Rolling
Stone had a great line about the first album,
called it unfathomably obscene and undeniably
offensive. Sounds about right. But then they
added it was also goddamn funny, and importantly,
far from just an X -rated novelty record. Ah,
so they acknowledged the music itself had merit.
It wasn't just shock value. Exactly. That validation
was huge. It framed him less as just a prankster
and more as this. weirdly legitimate, profane
critic of the genre. The sources call him an
experiment in free speech, right? A platform
against censorship. Yeah, his success became
this walking, talking argument against the sanitized
Nashville mainstream. And the reach became global,
didn't it? Wasn't there a stat about streaming?
By 2021, yeah. He was reportedly the third most
streamed country artist worldwide. Third? That's
insane. Ahead of probably dozens of artists getting
constant radio play. Built entirely on organic
demand for the explicit stuff. It shows the power
of finding your niche online. And he leaned into
that digital world, right, with podcasts. Oh,
yeah, masterfully. He did all the big ones, often
in character. Joe Rogan, Your Mom's House, Church
of What's Happening Now, Burt Kass. Howard Stern's
wrap -up show, too. These aren't just podcasts.
They're huge communities. He bypassed traditional
music press and talked directly to his audience
as the uncensored guy they loved. Cultivating
that authenticity, the realness, even if it's
amplified absurdity, something the polished acts
couldn't really match. Totally. His success really
proved that for a certain segment of the audience,
raw authenticity beats slick production every
time. Okay, so if you're positioning yourself
as this anti -censorship, anti -establishment
figure, conflict is going to follow, right? It's
pretty much guaranteed. Yeah. And yeah, it found
Wheeler pretty quickly, showed where the industry
lines were drawn. What was the first big clash?
Around the second album, Old Wheeler, in 2017.
He was using Pledge Music, the crowdfunding site,
for pre -orders. letting fans fund the uncensored
thing directly. Smart move. Direct support. Until
Pledge Music pulled the whole campaign, refunded
everyone. Why? Too many complaints about obscenity.
Oh, so the platform blinked. They did. And Hoffman,
of course, framed it immediately as censorship,
which fired up his fan base. And didn't his fans
do something weird in response? Yeah. This is
peak Wheeler fan base. They got angry about the
censorship and decided to troll the band Three
Love Evan online. 311, why them? Apparently,
they somehow thought 311 was responsible. It
makes no sense, but it perfectly shows the fan
base. Loyal, angry, maybe a little misguided,
but ready to fight the perceived system. Dedicated
absurdity. Okay, but the conflicts went higher
up than pledge music, right? Into actual Nashville.
Oh, yeah. The biggest example involves Maren
Morris. Grammy winner Maren Morris, big star.
The very same. They'd recorded a duet for Old
Wheeler, a song called Fuckin' Around. Okay.
But Sony Music Nashville, her label, pulled the
plug. Said she couldn't be on the track. Pulled
it right before the album release. Wow. So the
major label directly intervened. Our clean star
can't associate with this. Pretty much sums it
up. Even though, ironically, Hoffman had actually
performed with Morris and Jake Owen at a CMA
Awards afterparty the year before. So there was
some connection. But the official association
on an album, too far for some. Exactly. It shows
you the corporate firewall. But Hoffman found
a way around it. He still recorded the song.
Got Nikki Lane, another great singer -songwriter,
to do the duet instead. But on the album, she's
credited as Casey Walker. Ah, Casey Walker. Nice
little wink there. Kept the song, avoided the
label issue. Clever. Very clever. But despite
these fights, his live career just took off.
The online success definitely translated to ticket
sales. He toured a lot between 2016 and 2018.
Extensively across the U .S. And not just tiny
clubs. He started getting into bigger scenes,
bridging gaps. Like touring with Kid Rock. Yeah.
Summer 2018. Kid Rock and Brantley Gilbert on
the Red -Blooded Rock and Roll Redneck Extravaganza
Tour. Okay, that positioning makes sense. Leaning
into that rock outlaw crossover audience. Allowed
him to play to that crowd but still be the satirical
voice from within it, almost. But he also got
embraced by the more serious Americana side,
too. How so? There's footage from Himmerlin Music
Festival in 2018. He's on stage performing Sit
on My Face. Classy. Alongside Tyler Childers
and Sturgill Simpson. Whoa. Okay, that's significant.
Childers and Simpson are like the flag bearers
for modern, respected, non -mainstream country
and Americana. Exactly. Sharing a stage with
them. Performing that song. It shows they got
the joke. They respected the musicality or the
audacity or both. He was accepted by the serious
crowd. And didn't he present an award around
that time, too? Yep. Later that year, at the
Eric Conner Music Honors and Awards, Hoffman,
in full Wheeler character, presented an award
to Tyler Shoulders. That image is amazing. The
crude satire guy honoring the critically acclaimed
artist at their own award show. It shows the
complexity, right? The industry might reject
the lyrics. But parts of it clearly respected
the music and the whole project. Okay, fast forward
a bit. After the touring died down, there was
that big incident in 2022. The protest. Ah, yeah.
The Country Music Hall of Fame incident. Classic
Wheeler really captured his whole point. He got
kicked out, right? By security. Yep. Removed
from the property. Because he was protesting
the Florida -Georgia Line exhibit. FGL Prime.
Bro country example. Exactly. He had a sign,
apparently, saying FGL does not belong here.
Why? What was his argument? His long -running
argument. Their music is pop, not country. Putting
them in the Hall of Fame degrades what country
music is. degrades its history. So it was a physical
manifestation of his core satire, taking the
fight right to the heart of the Nashville establishment.
Perfectly execute a piece of performance art,
really. Got tons of publicity, obviously, which
only helped the narrative. The narrative of Wheeler
as the real outlaw fighting for country music's
soul. You got it. And it was the perfect setup
for his comeback. The 2022 comeback tour, which
kicked off where? At the Ryman Auditorium in
Nashville, the mother church of country music.
Headlining the Ryman. After getting kicked off
the Hall of Fame grounds, the symbolism. Oh,
it's perfect. His first live show since 2018.
And how did he promote it? By joking he wanted
to get canceled. Master of anti -marketing. Using
the culture war buzzwords, ironically. And did
it work? The show sold out instantly. And, according
to the sources, it broke the Ryman's records
for alcohol and merchandise sales. Broke the
bar record. And the merch record. That's what
the sources claim. Which is maybe even more telling
than just selling tickets. How so? It proves
the brand is potent. People weren't just buying
a ticket. They were buying into the whole Wheeler
Walker Jr. outlaw lifestyle fantasy. Yeah. Drinking.
Buying the T -shirts, huge loyalty and engagement.
It proved the whole uncensored satirical thing
was massively profitable when you connect directly
with that audience. OK, so let's quickly run
through the actual music, the albums that built
this whole phenomenon. Five studio albums now,
plus a compilation. That's right. All credited
to Wheeler Walker Jr., all part of this sustained
performance. And the chart performance was consistent,
as we said. Redneck shit, 2016. Number one comedy,
number nine country. Old Wheeler, 2017. Number
one comedy again, number ten country. Set the
pattern. Then WWIII in 2018. That one also topped
the comedy chart and hit number one on the overall
iTunes country chart. Showed his strength in
digital sales was huge. Right. Then the comeback
album in 2022, Sex, Drugs, and Country Music.
Timed with the tour and - the protest. Smart
timing. Debut number one on iTunes again. Number
two on the comedy albums chart. Kept the momentum
strong. And the latest, 2023, is ROM. Yep. And
ROM is interesting because the sources mention
a bit of a sound shift. How so? More rock -oriented.
A bit heavier than the earlier stuff. Okay. That's
a potentially important evolution. Why? Well,
it keeps things fresh, right? If you just kept
making the exact same traditional country parody,
maybe the joke wears thin. Shifting towards rock.
Which a lot of modern outlaw or Americana artists
do anyway, like Sturgill or Childers dipping
into rock. Exactly. It keeps the music itself
evolving, potentially broadening the appeal or
just keeping his core fans engaged with the sound,
not just the lyrics. Outlaw country is always
flirted with rock, so it fits the persona. Keeps
the project dynamic. Makes sense. And there was
that compilation too, right? Fuck you, bitch.
All time greatest hits. Came out in 2020. Mostly
tracks from the first three albums, but had a
couple of new ones, Drunk as Fuck and Go Big
or Go Home. Even the Greatest Hits title is perfectly
on -brand. Zero subtlety. It's all marketing
shorthand. And the single titles around the albums
do the same job. Like for Rem. Singles like Money
and Bitches, Dump Truck, Finger Blast. Okay.
Yep. Subtle as a brick. And for sex, drugs, and
country music, you had Fucked by a Country Boy,
and She's a Country Music Fan. It really hammers
home this satirical point, doesn't it? Taking
those underlying, sometimes vaguely hinted at
themes in mainstream country, the objectification,
the simplistic view of relationships or life.
And just blowing them up, making them grotesquely
literal and explicit. The comedy comes from that
extreme amplification. He's basically saying,
if you guys were really honest, this is what
it would sound like, stripped of the radio polish.
This is the logical conclusion of your tropes,
without the corporate filter. It's a harsh critique
wrapped in the crudest possible package. Hashtag
tag tag outro. So wrapping this up, we've really
traced this incredible paradox. A guy who's a
total Hollywood insider. Emmy nominated writer,
producer. Uses all those skills and his own money
to create this completely offensive anti -establishment
persona. That becomes wildly successful, commercially
viable, and even critically relevant as a form
of musical commentary. So hopefully you, the
listener, now have that full picture. Ben Hoffman,
the mainstream pro, meticulously crafting Wheeler
Walker Jr., the ultimate outlaw. Achieving success
in both worlds simultaneously. Stability in Hollywood,
rebellion in Nashville, all built on refusing
to be censored. Which brings us to that final
thought, something for you to chew on. Right.
So think about that Ryman show again. Sold out,
breaking records for booze and merch. Think about
his total artistic freedom because he funds himself
and answers to no label. Does that financial
independence, that ability to be completely uncensored,
actually make Wheeler Walker Jr., the satirical
character, a truer representation of the original
outlaw country spirit, that rebellious anti -Nashville
attitude? Then maybe some of the serious signed
artists he's making fun of who might have to
compromise more. Exactly. Is the joke character
in a weird way more genuinely outlaw than the
real thing sometimes? Something to think about.