OK, I want to start today by putting you in a
very specific headspace. It's 1998. Right. You're
sitting in a movie theater or, you know, maybe
you're watching a VHS rental a year later and
you're watching the Coen Brothers cult classic,
The Big Lebowski. A cultural touchstone. For
sure. Absolutely. So picture the bowling alley
scene. You know the one I'm talking about. Oh,
yeah. You've got. John Goodman's character, Walter
Sobchak, this volatile, shouting Vietnam vet
who treats league bowling like it's life and
death. He's terrified. And he gets into this
argument over a foul. Over the line. Exactly.
He's screaming about rules and he literally pulls
a handgun out of his bowling bag and pointed
at the guy on the other team. The guy he's threatening
is named Smokey. Market zero Smokey. Right. And
Smokey is just this, this. A terrified, fragile
pacifist with a gray ponytail just trembling
in the face of this absolute maniac. That's just
hilarious. Chaotic scene. It is. But here is
the reveal that always, always does people's
minds. That fragile pacifist, the guy playing
Smokey. He wasn't just some character actor they
picked out of a lineup. No. That was Jimmy Dale
Gilmore, a legitimate, honest -to -God Texas
country music legend. A man whose voice has been
described as, and I love this quote, a cross
between a coyote and a choir boy. That is maybe
the most accurate description I have ever heard.
And what's funny is that the character of Smokey,
you know, the gentle, slightly confused pacifist,
it isn't actually that far removed from the real
man. And that is exactly what we are unpacking
today. We are doing a deep dive into the life,
the music. the weirdly winding path of Jimmy
Dale Gilmore. Right. And I have to say, looking
at the research you pulled together, this is
not your standard musician gets famous, buys
a mansion, retires story. No, not even close.
It is a story about geography, about these incredible
historical coincidences, and honestly, about
the courage to just walk away from everything,
to sit in a room and meditate for 10 years. It's
wild. Our mission today is to figure out how
a kid from the Texas panhandle helped invent
a genre called progressive country, why he vanished
into a metaphysical ashram right when he should
have been getting famous, and how he ended up
as this sort of zen master of American music.
And, of course, a bowling icon. Can't forget
the bowling. Yeah. So let's start at the roots.
To understand Jimmy Dale Gilmore, I feel like
you have to understand... the dirt he was standing
on the geography is absolutely essential here
jimmy was born on may 6 1945 in amarillo but
he was really raised in lubbock texas now for
listeners who haven't had the pleasure of driving
through the texas panhandle we really need to
paint this picture because it is distinct it
is lubbock is flat i mean aggressively flat it
is incredibly windy it is dusty and back in the
1950s it was technically dry so no alcohol sold
legally it was a very conservative religious
isolated place it sounds Well, a little bleak,
to be honest. It can be. But there is this theory
in music history that isolation breeds creativity,
and specifically that the wind in Lubbock affects
the way people sing. Yeah, it creates this high
lonesome sound. You have to sing through the
wind to be heard, you know. Jimmy grew up in
that environment. And he had the musical foundation
right inside the house, didn't he? He did. His
father played guitar in a country band. But we
need to be specific here. This wasn't the polished
rhinestone. Nashville sound that became famous
on TV later. This was honky -tonk. Okay, let's
pause on that term, honky -tonk. We hear it a
lot, but what does it actually mean in a technical
sense? Great question. So before this era, country
music was often called hillbilly music or western
swing. Honky -tonk is the music of the bar room.
It emerged in the post -war era. It's characterized
by a heavy beat so people can dance to it and
lyrics that are very raw. We're talking heartbreak,
drinking, infidelity. hard life right the instrumentation
usually features a fiddle and a steel guitar
designed to cut through the noise of a crowded
rowdy bar think hank williams that is the dna
jimmie dale gilmore was born into so he's got
hank williams on one shoulder he's got the west
texas wind on the other but then you flagged
this specific date in the research october 15
1955 you called this his big bang moment This
is one of those historical coincidences that
feels like it was written for a movie script.
Jimmy is 10 years old. He goes to the Fair Park
Coliseum in Lubbock for a concert. And the lineup
for this single show is just, it's absolutely
insane. Lay it on us. Who was there? Okay, so
opening the show is a young local kid from Lubbock
named Buddy Holly. Okay, legend. Right there.
Then you have a guy named Johnny Cash. The man
in black himself. In the headliner. Don't say
it. Elvis Presley. Stop it. All three. In Lubbock,
in 1955. All on three, on the same stage. And
you have to imagine what this does to a 10 -year
-old boy's brain. Oh, my God. You have the raw
storytelling power of Johnny Cash. You have the
sex appeal and R &B rhythm of Elvis. And then
you have Buddy Holly, who is effectively taking
country music and just speeding it up to invent
rock and roll. Talk about being at the crossroads.
Exactly. Jimmy was standing at the convergence
of American music before he even hit puberty.
And that night... basically rewired his brain.
He realized music didn't have to be just one
thing. It could be all of it. That explains so
much about his later style. Because when you
listen to Gilmore, he doesn't fit neatly into
the country box. He's not just singing about
trucks. Right. And as he moved into the 1960s,
that palette just kept expanding. He didn't stop
at Elvis. He started absorbing the British invasion.
The Beatles, specifically. And he got really
into Bob Dylan and the whole folk and blues revival.
So he starts mixing it all up. He started mixing
that high, lonesome West Texas sound with the
intellectual curiosity of the folk movement.
Which brings us to the 1970s. And this is where
the legend really begins. He teams up with two
other guys who are now considered titans of Texas
music. Joe Ely and Butch Hancock. The Holy Trinity
of Lummock, as some people call them. And they
form a band with one of the best names in history.
The Flatlanders. It's the perfect name. It just
owns their geography. But here is the part that
confuses me. I look at music history books now,
and the Flatlanders are cited as this super influential
group. But in 1972, they were kind of a disaster,
right? Commercially. An absolute disaster. They
went to Nashville to record, thinking they had
something special, and Nashville hated them.
Why? I mean, if they were so talented, why did
Nashville reject them? Because they were weird.
They were doing something that didn't exist yet.
They were playing country music, but the lyrics
were poetic and strange, very Dylan -esque. And
this is a key detail. They used a musical saw.
A musical saw, like a literal carpentry saw that
you play with a bow. Yes. Steve Wesson, their
bandmate, played the musical saw. It makes this
eerie, ghostly, high -pitched sound, almost like
a theremin in a sci -fi movie. Wow. So imagine
walking into a polished Nashville studio in 1972
where everyone is trying to make smooth radio
hits and these long -haired Texans walk in with
a carpentry saw and songs about the cosmos. Okay,
I get to see the executives just sweating. It
was too much. The record label barely released
it. They put it out on eight -track tape with
almost zero distribution and then just buried
it. The band broke up shortly after. And that
was it. Everyone went their separate ways. It
was, by all accounts, a failure. But we're talking
about them now. Because of the slow burn. Over
the next nearly 20 years, bootleg tapes of that
session started circulating among musicians.
Songwriters would hear it and go, wait, what
is this? It became a secret handshake. Finally,
in 1990, nearly two decades later, Rounder Records
reissued the album. And they gave it that incredible
title. More a legend than a band. That is such
a flex. I love it. It really is. And by 1990,
the world had finally caught up. We had Alternative
Country and Americana by then. People realized
the Flatlanders had basically invented that sound
20 years too early. It's the classic ahead of
their time story. So the Flatlanders break up
in the 70s. Joe Ely goes on to have a rocking
solo career. He tours with The Clash, actually.
Right. Bush Hancock keeps running. But Jimmy
Dale Gilmore? He takes a left turn. A hard left
turn. This is the metaphysical detour. And I
think this is what makes Jimmy truly unique.
Most people, after a band fails, they either
quit music to sell insurance or they hustle harder.
The grind. They move to Nashville. They get a
job waiting tables. They write songs every day.
The standard playbook. But not Jimmy. Jimmy Gilmore
didn't grind. He went to Denver. And he moved
into an ashram. An ashram in Denver. Yes. He
became a follower of Prem Rawat, who was this
teenage Indian guru, also known as Maharaji.
And we aren't talking about a weekend yoga retreat.
Jimmy spent most of the 1970s living in this
community, studying metaphysics and meditation.
Okay. I need to understand the connection here.
How do you go from honky -tonk, which is beer,
trucks, cheating, and dusty bars, to Indian metaphysics?
They seem like polar opposites. Are they, though?
That's the question. Tell me more. How do you
connect those dots? Think about the very best
country songs. What are they about? They are
about suffering. They are about the human condition.
Why did she leave me? Why is life so hard? I'm
so lonesome I could cry. Metaphysics asks the
exact same questions, just with bigger vocabulary.
It asks, what is the nature of suffering? Is
the loneliness real? What is reality? That is
fascinating. So he was basically taking the my
dog died country trope and elevating it to does
the dog even exist? Laughs, essentially. And
this is what defines progressive country or the
cosmic cowboy scene that was bubbling up in Austin.
It's this collision of the redneck and the hippie.
Right. It's guys who wear cowboy boots but read
Eastern philosophy. Jimmy didn't see a contradiction.
He realized that the high lonesome sound was
actually a spiritual sound. It was searching
for something. But for his career. Surely this
was suicide. He vanished for a decade. In the
short term, yes, he was a ghost in the industry.
But this is the key insight for our listeners.
Sometimes stepping away creates the mystique
that makes you a legend. When he finally came
back to Austin in the 1980s, he wasn't just another
guy looking for a gig. He was different. He was
the sage. He had this weight to him. He had lived
a different kind of life. He brought the metaphysics
back to the music. Exactly. So let's talk about
the return. It's the 1980s. He decides he's ready.
He moves to Austin, which is really booming as
a music hub by then. Right. And he launches his
solo career properly. He releases his first solo
album, Fair and Square, in 1988. Then comes...
After a while in 1991. And the critics absolutely
loved it. They went nuts. He starts getting Grammy
nominations. And if you look at the categories,
it tells you everything about his versatility.
Okay. In 1993, he was nominated for Best Contemporary
Folk Album for Spitting Around the Sun. Contemporary
Folk. Got it. Then in 1996, another nomination
for Best Contemporary Folk Album for Braver,
Newer World. So consistent. But then later in
2005, he gets nominated for Best Traditional
Folk Album for Come On Back. Ah, so he can do
the new stuff. the old stuff precisely that album
come on back was a tribute project he recorded
songs his father loved yeah so he went from the
ashram back to the very roots we talked about
in the beginning i want to drill down on his
voice for a second because if you've never heard
jimmy deal gilmore it's hard to explain it's
not No, it is not smooth. It's incredibly distinctive.
It's nasal and it has this heavy vibrato, that
wavering sound. Some people call it a warble.
It's not pretty in the conventional pop sense.
It's haunting. It sounds ancient. It sounds like
the wind in Lubbock. And I have to imagine that
voice and that face is what drew in the filmmakers.
100%. Directors love authenticity. and jimmy
just radiates it you can't act that kind of weariness
and peace which brings us right back to the big
lebowski the cohen brothers needed someone to
play smoky The character is a pacifist, but he's
in a bowling league, which is a very working
class structured environment. Casting Jimmy was
genius because Jimmy is that paradox. He's the
country boy who went to the ashram. He doesn't
have to act like a guy who has seen some things
and decided to be peaceful. He is that guy. Over
the line. It's perfect. And that wasn't his only
role. He actually played himself in a movie,
right? He did. In 1993, he was in Peter Bogdanovich's
film The Thing Called Love. It was a story about
young songwriters trying to make it in Nashville.
Oh, with River Phoenix. That's the one. And it
makes sense if you're making a movie about the
struggle of songwriters to be authentic. Jimmy
is the ultimate example of the pure artist who
didn't sell out. And his music made it into films,
too. Yes. His song Braver, Newer World was featured
in the 1995 Noah Baumbach film Kicking and Screaming.
And more recently, his cover of Mack the Knife,
which is from his album One Endless Night, ended
up on the soundtrack of the 2009 film A Prophet.
Mack the Knife. The Bobby Darin swing song. Yes,
but Jimmy slows it way down. He makes it acoustic
and creepy. It fits perfectly in a French crime
drama. Wow. It just shows that his voice transcends
the country label. It works in a French prison
movie just as well as a Texas honky -tonk. I
also saw a note here about Willie Nelson. You
can't have a Texas deep dive without Willie.
It's basically the law in Texas. Did their pads
cross? They certainly did, and for a very important
cause. In 1994, Gilmore teamed up with Willie
Nelson to sing the song Crazy for the album Red
Hot Plus Country. Oh, that album. This was an
AIDS benefit album produced by the Red Hot organization.
That's amazing. Yeah. And huge at the time because
country music wasn't exactly known for being
at the forefront of AIDS activism in the early
90s. No, it wasn't. And that's the progressive
part of Jimmy again. He and Willie coming together
for that showed that the Texas music scene was
inclusive in a way that the mainstream industry
wasn't always ready to be. It was a statement.
And speaking of legacy and passing the torch,
the musical gene didn't stop with Jimmy. No,
it didn't. We should mention his son, Colin Gilmore.
He's also a fantastic singer -songwriter based
in Austin. Oh, cool. He's got a bit of that Gilmore
DNA in his voice, but he's doing his own thing,
so the lineage is safe. So let's zoom out a bit.
We've covered a lot of ground here. We went from
that Coliseum in Lubbock watching Elvis and Buddy
Holly. To the lost recordings and the musical
saw of the Flatlander. To the silence of the
ashram in Denver. And finally, to the Grammy
nominations and the bowling alley in the Big
Lebowski. When you step back and look at the
whole map, what is the core lesson here? What
defines Jimmy Dill Gilmore? For me, it's the
redefinition of success. How so? Well, the music
industry tells you that success is a straight
line. You start, you get a hit, you get a bigger
hit, you play stadiums. Jimmy proved that success
is actually about identity. Right. He didn't
fit in Nashville, so he didn't go. He needed
spiritual answers, so he left the business entirely.
He let his first band be a failure for 20 years
before capitalizing on it. To lay the long game.
The longest game. And because of that, he never
became a parody of himself. He never became just
another oldies act. He remained an artist. He
represents that specific Texas idea that you
can be a cosmic cowboy. You can love your roots,
love the land, and still have your head in the
stars asking big philosophical questions. I love
that image, the cosmic cowboy. It's really the
only way to explain him. I want to leave our
listeners with a final thought to mull over.
Something that struck me while we were researching
his lost decade. Let's hear it. We live in a
culture now, especially with social media, where
if you aren't posting, you don't exist. If you
aren't optimizing your career every single day,
you feel like you're falling behind. The hustle
culture. It's relentless. Exactly. But Jimmy
Dale Gilmore stopped. He just stopped. And everyone
probably told him he was crazy. You're throwing
it all away. But looking back, that silence,
that's where the magic accumulated. Yeah. If
he hadn't gone to the ashram, he wouldn't be
the Jimmy Dale Gilmore we know. He'd just be
another country singer. That's a powerful takeaway.
The pause isn't the end of the song. It's part
of the rhythm. Precisely. So if you're feeling
stuck right now or if you feel like you've stepped
off the path, maybe you're just in your ashram
phase. And the best work your legend phase is
waiting for you when you're ready to come back.
I love that a lot. Thanks for joining us on this
deep dive into the flatlands and the cosmos with
Jimmy Dale Gilmore. It's been a pleasure. See
you next time.