WEBVTT

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OK, I want to start today by putting you in a

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very specific headspace. It's 1998. Right. You're

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sitting in a movie theater or, you know, maybe

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you're watching a VHS rental a year later and

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you're watching the Coen Brothers cult classic,

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The Big Lebowski. A cultural touchstone. For

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sure. Absolutely. So picture the bowling alley

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scene. You know the one I'm talking about. Oh,

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yeah. You've got. John Goodman's character, Walter

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Sobchak, this volatile, shouting Vietnam vet

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who treats league bowling like it's life and

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death. He's terrified. And he gets into this

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argument over a foul. Over the line. Exactly.

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He's screaming about rules and he literally pulls

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a handgun out of his bowling bag and pointed

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at the guy on the other team. The guy he's threatening

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is named Smokey. Market zero Smokey. Right. And

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Smokey is just this, this. A terrified, fragile

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pacifist with a gray ponytail just trembling

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in the face of this absolute maniac. That's just

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hilarious. Chaotic scene. It is. But here is

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the reveal that always, always does people's

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minds. That fragile pacifist, the guy playing

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Smokey. He wasn't just some character actor they

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picked out of a lineup. No. That was Jimmy Dale

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Gilmore, a legitimate, honest -to -God Texas

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country music legend. A man whose voice has been

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described as, and I love this quote, a cross

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between a coyote and a choir boy. That is maybe

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the most accurate description I have ever heard.

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And what's funny is that the character of Smokey,

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you know, the gentle, slightly confused pacifist,

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it isn't actually that far removed from the real

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man. And that is exactly what we are unpacking

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today. We are doing a deep dive into the life,

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the music. the weirdly winding path of Jimmy

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Dale Gilmore. Right. And I have to say, looking

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at the research you pulled together, this is

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not your standard musician gets famous, buys

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a mansion, retires story. No, not even close.

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It is a story about geography, about these incredible

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historical coincidences, and honestly, about

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the courage to just walk away from everything,

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to sit in a room and meditate for 10 years. It's

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wild. Our mission today is to figure out how

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a kid from the Texas panhandle helped invent

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a genre called progressive country, why he vanished

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into a metaphysical ashram right when he should

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have been getting famous, and how he ended up

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as this sort of zen master of American music.

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And, of course, a bowling icon. Can't forget

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the bowling. Yeah. So let's start at the roots.

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To understand Jimmy Dale Gilmore, I feel like

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you have to understand... the dirt he was standing

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on the geography is absolutely essential here

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jimmy was born on may 6 1945 in amarillo but

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he was really raised in lubbock texas now for

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listeners who haven't had the pleasure of driving

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through the texas panhandle we really need to

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paint this picture because it is distinct it

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is lubbock is flat i mean aggressively flat it

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is incredibly windy it is dusty and back in the

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1950s it was technically dry so no alcohol sold

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legally it was a very conservative religious

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isolated place it sounds Well, a little bleak,

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to be honest. It can be. But there is this theory

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in music history that isolation breeds creativity,

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and specifically that the wind in Lubbock affects

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the way people sing. Yeah, it creates this high

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lonesome sound. You have to sing through the

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wind to be heard, you know. Jimmy grew up in

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that environment. And he had the musical foundation

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right inside the house, didn't he? He did. His

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father played guitar in a country band. But we

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need to be specific here. This wasn't the polished

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rhinestone. Nashville sound that became famous

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on TV later. This was honky -tonk. Okay, let's

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pause on that term, honky -tonk. We hear it a

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lot, but what does it actually mean in a technical

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sense? Great question. So before this era, country

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music was often called hillbilly music or western

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swing. Honky -tonk is the music of the bar room.

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It emerged in the post -war era. It's characterized

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by a heavy beat so people can dance to it and

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lyrics that are very raw. We're talking heartbreak,

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drinking, infidelity. hard life right the instrumentation

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usually features a fiddle and a steel guitar

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designed to cut through the noise of a crowded

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rowdy bar think hank williams that is the dna

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jimmie dale gilmore was born into so he's got

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hank williams on one shoulder he's got the west

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texas wind on the other but then you flagged

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this specific date in the research october 15

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1955 you called this his big bang moment This

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is one of those historical coincidences that

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feels like it was written for a movie script.

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Jimmy is 10 years old. He goes to the Fair Park

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Coliseum in Lubbock for a concert. And the lineup

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for this single show is just, it's absolutely

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insane. Lay it on us. Who was there? Okay, so

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opening the show is a young local kid from Lubbock

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named Buddy Holly. Okay, legend. Right there.

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Then you have a guy named Johnny Cash. The man

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in black himself. In the headliner. Don't say

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it. Elvis Presley. Stop it. All three. In Lubbock,

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in 1955. All on three, on the same stage. And

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you have to imagine what this does to a 10 -year

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-old boy's brain. Oh, my God. You have the raw

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storytelling power of Johnny Cash. You have the

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sex appeal and R &amp;B rhythm of Elvis. And then

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you have Buddy Holly, who is effectively taking

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country music and just speeding it up to invent

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rock and roll. Talk about being at the crossroads.

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Exactly. Jimmy was standing at the convergence

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of American music before he even hit puberty.

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And that night... basically rewired his brain.

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He realized music didn't have to be just one

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thing. It could be all of it. That explains so

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much about his later style. Because when you

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listen to Gilmore, he doesn't fit neatly into

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the country box. He's not just singing about

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trucks. Right. And as he moved into the 1960s,

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that palette just kept expanding. He didn't stop

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at Elvis. He started absorbing the British invasion.

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The Beatles, specifically. And he got really

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into Bob Dylan and the whole folk and blues revival.

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So he starts mixing it all up. He started mixing

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that high, lonesome West Texas sound with the

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intellectual curiosity of the folk movement.

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Which brings us to the 1970s. And this is where

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the legend really begins. He teams up with two

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other guys who are now considered titans of Texas

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music. Joe Ely and Butch Hancock. The Holy Trinity

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of Lummock, as some people call them. And they

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form a band with one of the best names in history.

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The Flatlanders. It's the perfect name. It just

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owns their geography. But here is the part that

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confuses me. I look at music history books now,

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and the Flatlanders are cited as this super influential

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group. But in 1972, they were kind of a disaster,

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right? Commercially. An absolute disaster. They

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went to Nashville to record, thinking they had

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something special, and Nashville hated them.

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Why? I mean, if they were so talented, why did

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Nashville reject them? Because they were weird.

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They were doing something that didn't exist yet.

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They were playing country music, but the lyrics

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were poetic and strange, very Dylan -esque. And

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this is a key detail. They used a musical saw.

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A musical saw, like a literal carpentry saw that

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you play with a bow. Yes. Steve Wesson, their

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bandmate, played the musical saw. It makes this

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eerie, ghostly, high -pitched sound, almost like

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a theremin in a sci -fi movie. Wow. So imagine

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walking into a polished Nashville studio in 1972

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where everyone is trying to make smooth radio

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hits and these long -haired Texans walk in with

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a carpentry saw and songs about the cosmos. Okay,

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I get to see the executives just sweating. It

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was too much. The record label barely released

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it. They put it out on eight -track tape with

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almost zero distribution and then just buried

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it. The band broke up shortly after. And that

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was it. Everyone went their separate ways. It

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was, by all accounts, a failure. But we're talking

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about them now. Because of the slow burn. Over

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the next nearly 20 years, bootleg tapes of that

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session started circulating among musicians.

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Songwriters would hear it and go, wait, what

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is this? It became a secret handshake. Finally,

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in 1990, nearly two decades later, Rounder Records

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reissued the album. And they gave it that incredible

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title. More a legend than a band. That is such

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a flex. I love it. It really is. And by 1990,

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the world had finally caught up. We had Alternative

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Country and Americana by then. People realized

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the Flatlanders had basically invented that sound

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20 years too early. It's the classic ahead of

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their time story. So the Flatlanders break up

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in the 70s. Joe Ely goes on to have a rocking

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solo career. He tours with The Clash, actually.

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Right. Bush Hancock keeps running. But Jimmy

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Dale Gilmore? He takes a left turn. A hard left

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turn. This is the metaphysical detour. And I

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think this is what makes Jimmy truly unique.

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Most people, after a band fails, they either

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quit music to sell insurance or they hustle harder.

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The grind. They move to Nashville. They get a

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job waiting tables. They write songs every day.

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The standard playbook. But not Jimmy. Jimmy Gilmore

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didn't grind. He went to Denver. And he moved

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into an ashram. An ashram in Denver. Yes. He

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became a follower of Prem Rawat, who was this

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teenage Indian guru, also known as Maharaji.

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And we aren't talking about a weekend yoga retreat.

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Jimmy spent most of the 1970s living in this

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community, studying metaphysics and meditation.

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Okay. I need to understand the connection here.

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How do you go from honky -tonk, which is beer,

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trucks, cheating, and dusty bars, to Indian metaphysics?

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They seem like polar opposites. Are they, though?

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That's the question. Tell me more. How do you

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connect those dots? Think about the very best

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country songs. What are they about? They are

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about suffering. They are about the human condition.

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Why did she leave me? Why is life so hard? I'm

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so lonesome I could cry. Metaphysics asks the

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exact same questions, just with bigger vocabulary.

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It asks, what is the nature of suffering? Is

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the loneliness real? What is reality? That is

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fascinating. So he was basically taking the my

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dog died country trope and elevating it to does

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the dog even exist? Laughs, essentially. And

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this is what defines progressive country or the

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cosmic cowboy scene that was bubbling up in Austin.

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It's this collision of the redneck and the hippie.

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Right. It's guys who wear cowboy boots but read

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Eastern philosophy. Jimmy didn't see a contradiction.

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He realized that the high lonesome sound was

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actually a spiritual sound. It was searching

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for something. But for his career. Surely this

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was suicide. He vanished for a decade. In the

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short term, yes, he was a ghost in the industry.

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But this is the key insight for our listeners.

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Sometimes stepping away creates the mystique

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that makes you a legend. When he finally came

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back to Austin in the 1980s, he wasn't just another

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guy looking for a gig. He was different. He was

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the sage. He had this weight to him. He had lived

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a different kind of life. He brought the metaphysics

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back to the music. Exactly. So let's talk about

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the return. It's the 1980s. He decides he's ready.

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He moves to Austin, which is really booming as

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a music hub by then. Right. And he launches his

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solo career properly. He releases his first solo

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album, Fair and Square, in 1988. Then comes...

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After a while in 1991. And the critics absolutely

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loved it. They went nuts. He starts getting Grammy

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nominations. And if you look at the categories,

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it tells you everything about his versatility.

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Okay. In 1993, he was nominated for Best Contemporary

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Folk Album for Spitting Around the Sun. Contemporary

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Folk. Got it. Then in 1996, another nomination

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for Best Contemporary Folk Album for Braver,

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Newer World. So consistent. But then later in

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2005, he gets nominated for Best Traditional

00:11:10.750 --> 00:11:13.769
Folk Album for Come On Back. Ah, so he can do

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the new stuff. the old stuff precisely that album

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come on back was a tribute project he recorded

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songs his father loved yeah so he went from the

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ashram back to the very roots we talked about

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in the beginning i want to drill down on his

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voice for a second because if you've never heard

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jimmy deal gilmore it's hard to explain it's

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not No, it is not smooth. It's incredibly distinctive.

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It's nasal and it has this heavy vibrato, that

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wavering sound. Some people call it a warble.

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It's not pretty in the conventional pop sense.

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It's haunting. It sounds ancient. It sounds like

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the wind in Lubbock. And I have to imagine that

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voice and that face is what drew in the filmmakers.

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100%. Directors love authenticity. and jimmy

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just radiates it you can't act that kind of weariness

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and peace which brings us right back to the big

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lebowski the cohen brothers needed someone to

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play smoky The character is a pacifist, but he's

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in a bowling league, which is a very working

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class structured environment. Casting Jimmy was

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genius because Jimmy is that paradox. He's the

00:12:18.120 --> 00:12:20.940
country boy who went to the ashram. He doesn't

00:12:20.940 --> 00:12:23.159
have to act like a guy who has seen some things

00:12:23.159 --> 00:12:26.279
and decided to be peaceful. He is that guy. Over

00:12:26.279 --> 00:12:28.519
the line. It's perfect. And that wasn't his only

00:12:28.519 --> 00:12:30.379
role. He actually played himself in a movie,

00:12:30.419 --> 00:12:34.200
right? He did. In 1993, he was in Peter Bogdanovich's

00:12:34.200 --> 00:12:36.980
film The Thing Called Love. It was a story about

00:12:36.980 --> 00:12:38.879
young songwriters trying to make it in Nashville.

00:12:39.100 --> 00:12:41.179
Oh, with River Phoenix. That's the one. And it

00:12:41.179 --> 00:12:43.100
makes sense if you're making a movie about the

00:12:43.100 --> 00:12:45.500
struggle of songwriters to be authentic. Jimmy

00:12:45.500 --> 00:12:48.980
is the ultimate example of the pure artist who

00:12:48.980 --> 00:12:51.379
didn't sell out. And his music made it into films,

00:12:51.419 --> 00:12:54.570
too. Yes. His song Braver, Newer World was featured

00:12:54.570 --> 00:12:57.710
in the 1995 Noah Baumbach film Kicking and Screaming.

00:12:57.909 --> 00:13:01.250
And more recently, his cover of Mack the Knife,

00:13:01.289 --> 00:13:04.149
which is from his album One Endless Night, ended

00:13:04.149 --> 00:13:06.789
up on the soundtrack of the 2009 film A Prophet.

00:13:07.009 --> 00:13:10.610
Mack the Knife. The Bobby Darin swing song. Yes,

00:13:10.649 --> 00:13:13.909
but Jimmy slows it way down. He makes it acoustic

00:13:13.909 --> 00:13:16.269
and creepy. It fits perfectly in a French crime

00:13:16.269 --> 00:13:19.129
drama. Wow. It just shows that his voice transcends

00:13:19.129 --> 00:13:21.409
the country label. It works in a French prison

00:13:21.409 --> 00:13:23.929
movie just as well as a Texas honky -tonk. I

00:13:23.929 --> 00:13:26.190
also saw a note here about Willie Nelson. You

00:13:26.190 --> 00:13:28.169
can't have a Texas deep dive without Willie.

00:13:28.389 --> 00:13:30.830
It's basically the law in Texas. Did their pads

00:13:30.830 --> 00:13:34.009
cross? They certainly did, and for a very important

00:13:34.009 --> 00:13:38.600
cause. In 1994, Gilmore teamed up with Willie

00:13:38.600 --> 00:13:42.279
Nelson to sing the song Crazy for the album Red

00:13:42.279 --> 00:13:45.919
Hot Plus Country. Oh, that album. This was an

00:13:45.919 --> 00:13:48.539
AIDS benefit album produced by the Red Hot organization.

00:13:49.159 --> 00:13:51.899
That's amazing. Yeah. And huge at the time because

00:13:51.899 --> 00:13:54.440
country music wasn't exactly known for being

00:13:54.440 --> 00:13:56.500
at the forefront of AIDS activism in the early

00:13:56.500 --> 00:13:59.320
90s. No, it wasn't. And that's the progressive

00:13:59.320 --> 00:14:02.360
part of Jimmy again. He and Willie coming together

00:14:02.360 --> 00:14:04.799
for that showed that the Texas music scene was

00:14:04.799 --> 00:14:06.980
inclusive in a way that the mainstream industry

00:14:06.980 --> 00:14:09.639
wasn't always ready to be. It was a statement.

00:14:09.820 --> 00:14:11.879
And speaking of legacy and passing the torch,

00:14:12.059 --> 00:14:14.639
the musical gene didn't stop with Jimmy. No,

00:14:14.679 --> 00:14:17.059
it didn't. We should mention his son, Colin Gilmore.

00:14:17.100 --> 00:14:19.419
He's also a fantastic singer -songwriter based

00:14:19.419 --> 00:14:21.779
in Austin. Oh, cool. He's got a bit of that Gilmore

00:14:21.779 --> 00:14:23.840
DNA in his voice, but he's doing his own thing,

00:14:23.879 --> 00:14:26.429
so the lineage is safe. So let's zoom out a bit.

00:14:26.450 --> 00:14:28.110
We've covered a lot of ground here. We went from

00:14:28.110 --> 00:14:30.289
that Coliseum in Lubbock watching Elvis and Buddy

00:14:30.289 --> 00:14:32.570
Holly. To the lost recordings and the musical

00:14:32.570 --> 00:14:34.970
saw of the Flatlander. To the silence of the

00:14:34.970 --> 00:14:38.110
ashram in Denver. And finally, to the Grammy

00:14:38.110 --> 00:14:40.389
nominations and the bowling alley in the Big

00:14:40.389 --> 00:14:42.929
Lebowski. When you step back and look at the

00:14:42.929 --> 00:14:46.149
whole map, what is the core lesson here? What

00:14:46.149 --> 00:14:48.490
defines Jimmy Dill Gilmore? For me, it's the

00:14:48.490 --> 00:14:51.470
redefinition of success. How so? Well, the music

00:14:51.470 --> 00:14:53.389
industry tells you that success is a straight

00:14:53.389 --> 00:14:55.990
line. You start, you get a hit, you get a bigger

00:14:55.990 --> 00:14:59.350
hit, you play stadiums. Jimmy proved that success

00:14:59.350 --> 00:15:01.950
is actually about identity. Right. He didn't

00:15:01.950 --> 00:15:04.250
fit in Nashville, so he didn't go. He needed

00:15:04.250 --> 00:15:06.730
spiritual answers, so he left the business entirely.

00:15:07.309 --> 00:15:11.029
He let his first band be a failure for 20 years

00:15:11.029 --> 00:15:13.129
before capitalizing on it. To lay the long game.

00:15:13.230 --> 00:15:15.830
The longest game. And because of that, he never

00:15:15.830 --> 00:15:18.950
became a parody of himself. He never became just

00:15:18.950 --> 00:15:22.649
another oldies act. He remained an artist. He

00:15:22.649 --> 00:15:25.230
represents that specific Texas idea that you

00:15:25.230 --> 00:15:27.750
can be a cosmic cowboy. You can love your roots,

00:15:27.850 --> 00:15:29.669
love the land, and still have your head in the

00:15:29.669 --> 00:15:32.340
stars asking big philosophical questions. I love

00:15:32.340 --> 00:15:34.879
that image, the cosmic cowboy. It's really the

00:15:34.879 --> 00:15:36.620
only way to explain him. I want to leave our

00:15:36.620 --> 00:15:38.679
listeners with a final thought to mull over.

00:15:39.220 --> 00:15:41.899
Something that struck me while we were researching

00:15:41.899 --> 00:15:45.039
his lost decade. Let's hear it. We live in a

00:15:45.039 --> 00:15:48.019
culture now, especially with social media, where

00:15:48.019 --> 00:15:51.039
if you aren't posting, you don't exist. If you

00:15:51.039 --> 00:15:53.620
aren't optimizing your career every single day,

00:15:53.740 --> 00:15:55.779
you feel like you're falling behind. The hustle

00:15:55.779 --> 00:15:58.539
culture. It's relentless. Exactly. But Jimmy

00:15:58.539 --> 00:16:01.750
Dale Gilmore stopped. He just stopped. And everyone

00:16:01.750 --> 00:16:03.509
probably told him he was crazy. You're throwing

00:16:03.509 --> 00:16:05.929
it all away. But looking back, that silence,

00:16:06.370 --> 00:16:09.309
that's where the magic accumulated. Yeah. If

00:16:09.309 --> 00:16:11.610
he hadn't gone to the ashram, he wouldn't be

00:16:11.610 --> 00:16:13.730
the Jimmy Dale Gilmore we know. He'd just be

00:16:13.730 --> 00:16:16.350
another country singer. That's a powerful takeaway.

00:16:16.610 --> 00:16:19.450
The pause isn't the end of the song. It's part

00:16:19.450 --> 00:16:22.690
of the rhythm. Precisely. So if you're feeling

00:16:22.690 --> 00:16:25.049
stuck right now or if you feel like you've stepped

00:16:25.049 --> 00:16:28.250
off the path, maybe you're just in your ashram

00:16:28.250 --> 00:16:31.059
phase. And the best work your legend phase is

00:16:31.059 --> 00:16:32.840
waiting for you when you're ready to come back.

00:16:33.059 --> 00:16:35.799
I love that a lot. Thanks for joining us on this

00:16:35.799 --> 00:16:38.379
deep dive into the flatlands and the cosmos with

00:16:38.379 --> 00:16:40.480
Jimmy Dale Gilmore. It's been a pleasure. See

00:16:40.480 --> 00:16:40.940
you next time.
