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Hidden Brain

The Cowboy Philosopher

May 11, 20261h 29m · 12,522 words

Show notes

In 2009, an old man died in a California nursing home. His obituary included not just his given name, but a long list of the pseudonyms he’d been known to use. In this classic 2019 episode, we trace the life of Riley Shepard, a hillbilly musician, writer, small-time con man and, perhaps, a genius. Then, on Your Questions Answered, psychologist Leslie John returns to answer your questions about when to share a secret, and when to keep it to yourself. You can find an online version of Riley Shepard's Encyclopedia of Folk Music here . There's a powerful tool almost all of us overlook when we're trying to improve a work project or help our kids with their homework. Learn more in this video on our new YouTube channel! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Highlighted moments

we have strong opinions about such people when they succeed when they produce the Taj Mahal or Hamlet or the iPhone we hail the obsessions that built the monuments of this world when we count the collateral damage that people with obsessions leave in their wake especially when those obsessions only produce the unreadable tome on the evil eye or an unpublishable encyclopedia on folk music obsessions start to look like folly
Jump to 49:08 in the transcript
he glamorized the life of being a grifter he glamorized the life of being a con that's what I understand now that he he was a con man it's even hard to say that out loud he was though
Jump to 25:15 in the transcript
my point isn't that we should say all of the things that are in our mind you don't want that but rather I think we should consider saying the things more
Jump to 1:32:08 in the transcript

Transcript

Introduction

0:00This is Hidden Brain. I'm Shankar Vedanta. Today's episode begins in a subterranean labyrinth. It's 2018, and we're below the streets of Washington, D.C. I've come here in search of clues. So here we are in Deck 50 in the stacks of the Library of Congress. I'm opening a door that's marked Door 20. My guide through the Library of Congress' massive collection is a tall, shaggy man. His name is Steve Winnick. He looks a lot like Hagrid from Harry Potter,

0:30which seems about right for someone with a title of folklorist. Steve has already led me through a maze of low-ceiling stacks, across a small bridge, and into a tiny elevator, where the flow numbers go up as we move down. Finally, we arrive at our destination. And in here, we find row upon row of collection boxes on the shelves, and I'm looking for this collection, which is numbered AFC 1979-008.

1:03Steve pulls from the shelf a cardboard box. Nobody's really used this collection very much, so it's simply, you know, been there waiting for you, really. The author of this collection is Richard Riley Shepard, a small-time crook and conman who died in 2009.

1:23I've been tracking Riley Shepard for a few months. My assumption is that there's nothing of significance in the box. But I'm about to discover that the story I thought I was reporting is not, in fact, the full story. The story that's about to unfold before me is a story of obsession, its power, its beauty, and its costs.

1:51This week on Hidden Brain, we bring you a classic episode about the peculiar life of a man named Riley Shepard. He was a musician and writer who spent decades on a single grand project. Whether that project was a great quest or a great folly, that is for you to decide.

2:12He was a genius, I think. He just was a compulsive liar. He was quite a master. Dick Scott, Hickey Free. He was getting out of town before he was being tart and tethered. I've got to get this done. They all hated my guts. So I said, what? I am.

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Discovering Riley Shepard

3:37I stumbled onto the story as I was contemplating an episode not about obsession, but about fallen heroes. I'd asked hidden-brained listeners to share examples from their own lives.

3:50One of the messages... I hope I did this right. ...was from Stasha Shepard-Silverman. She said her fallen hero was her dad, Riley Shepard, whom she still loved. I want to say that I had a great relationship with my father. He was totally cool in many ways and a great cook. Totally into... When we talk, Stasha tells me that as a young girl, she idolized her dad. She has memories of those days that feel like tiny, sparkling gems.

4:23My earliest memory of my dad is sitting on his lap and him smoking his cigar, and he would make cigar smoke rings for me. Stasha would watch them, transfixed, as they rose in the air before her. I thought the smoke rings were magical.

4:45There was a lot that was magical for Stasha back then. She still remembers their little apartment in Hollywood with the Siamese cat and the cat hair and the hardwood floors. She remembers how much she loved that her dad was around all the time. He didn't have a regular job. And he would sit in the middle of the living room, usually, wherever we lived, and he would type. So he was working on things. He was working on... I didn't know what.

5:15But I would sit under his desk sometimes while he typed away, and we would talk in between the pages, and he would tell me things about show business. They were in their own little bubble. Riley in his late 50s and his little daughter. Typing, talking, just being together.

5:34Sometimes, if Riley had a little money, he'd take Stasha out to eat at their favorite Hollywood hotspot, a restaurant called the Brown Derby. It was a place where Riley could rub shoulders with famous people, charm them with his warm Southern accent, and impress his daughter on their way home. You know, the Hollywood stars were all around us. We could walk up the street, and my father would tell me about movie stars when we walked. He seemed to know everything. Stasha was certain that her dad was something of a star himself.

6:05Sometimes he'd tell her about his musical career as a successful promoter, singer, and songwriter. Occasionally, he might even sing the song. His song. He told me and he told everyone that he wrote the song Blue Christmas.

6:34It wasn't true. Billy Hayes and Jay Johnson wrote Blue Christmas. The person who made it famous? Elvis.

6:53If Riley had written Blue Christmas, money might not have been so tight for the family. I was told constantly that we were artists, and that there were artists, and there were ordinary people, and we were artists. Stasha eventually learned about her dad's most important artistic endeavor, not a song, but a writing project. The Encyclopedia of Folk Music.

7:20And that was supposedly his life's work, and it was vast. I mean, there were boxes there, huge boxes of volumes of indexes and things he was working on in books. To fund its creation, Riley solicited money from investors, some of whom he convinced to pour thousands of dollars into the project. Sometimes investors and bill collectors would call to ask when they were going to get paid.

7:52He used to get on the phone with all kinds of people and say, you didn't get the check? What? The post office? He would constantly rail against the post office, so as a little girl, I also became very militant against the post office. I also would rail against the post office, and if I had a pen pal or a friend that I was writing a letter to, I would always write on the outside of the envelope, you better deliver this letter.

8:23You know, I was like enraged with the post office that they wouldn't deliver letters, because I just thought they're constantly throwing my dad under the bus and not mailing his checks.

8:37For many children, there is a moment when a curtain pulls back and parents are revealed for who they are, imperfect beings with flaws and failings. But for Starsha, the father she saw when the curtain opened was hard to recognize. It happened one day when she was 12, hanging out at home.

8:59And the phone rang. So I picked it up. I said hello. The caller demanded to speak to her dad. Starsha said he was out. His voice was shaking, and I could tell he was elderly.

9:13And he just sounded like a mean old man to me. He scared me. And he told me that my father took his life savings. The phone is in my ear, and he's saying, your father's a crook.

9:37Did you know that? Your father is a crook.

9:51How Starsha responded to that phone call when we come back. You're listening to Hidden Brain. I'm Shankar Vedanta.

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Riley's Music Career

10:48This is Hidden Brain. I'm Shankar Vedanta. In 1946, Riley Shepard released a cover of the hit song, Atomic Power. It was inspired by the bombings of Hiroshima and Nagasaki. Oh, this world is at a tremble With its strength and mighty power They're sending up to heaven To get the brimstone fire Riley was a rising talent. He had dark good looks, a soft southern twang,

11:19and the guitar skills to make a go of it. The mighty power of God's own holy hand He signed with various labels. He seemed like he was headed somewhere. The mighty hand of God But Riley Shepard never achieved stardom. Instead, his life took a series of detours. Music researcher and writer

11:52Kevin Coffey tracked Riley down many years ago. Riley at the time was 89. Kevin was interested in preserving the stories of old-time country Western performers. He thought Riley might be worth profiling. Von Horton, he played steel on a lot of your records. Von Horton played steel on all of them. The conversation they had over a crackly phone line was friendly and nostalgic and full of insider names most people wouldn't recognize.

12:22And Roy's wife played piano, Lily Horton. Oh, really? Yeah. Gradually, Kevin pieced together Riley's backstory.

12:34Richard Riley Shepard was born on a farm near Wilmington, North Carolina in 1918. He dropped out of school in the fifth grade and decided to try his luck at singing. It was a heady time for music in the region. Groups like the Mainers Mountaineers were popularizing what was then called hillbilly music.

12:55This world is not my home I'm just a-passing through Trajors in my home are far beyond the blues Where many friends have left me and have gone before And I can't feel at home in this world anymore Riley started out playing songs in minstrel shows. Soon, he told Kevin, he was getting gigs with hillbilly groups like the Dixie Reelers.

13:26I'm on my way to glory I shall not be moved I'm on my way to glory I shall not be moved Just like a tree By the early 1940s, Riley had moved to Chicago. He toured with other hillbilly musicians and did comedy and acting work. He also began cultivating his image as a cowboy crooner. As he created this new persona he gave himself a catchy moniker

13:56The Cowboy Philosopher Where did you come up with that? Because I know you were calling yourself the... I didn't come up with it Gene Auger came up with it Oh, did he? Because I found an ad from way back in 1945 and you were already using it back then So... Gene came up with that crap To top off his fancy new title of philosopher Riley grew a dashing mustache and began scheming up fresh ways to get into the spotlight The Cosmopolitan Church presents

14:26Dr. Richard Riley Shepard This is Tasha again A few years ago she found one of the old flyers that advertised her dad's lectures Dr. Richard Riley Shepard author, historian world traveler philosopher in a series of educational lectures The world traveler and philosopher was prepared to discuss a variety of important topics Saturday, October 10th God, man and science

14:56Saturday, October 17th Marriage Sex and morality Saturday, October 31st Democracy and capitalism Saturday, November 7th Origin and growth of fascism Saturday Even as he sought to make a name for himself with his educational lectures Riley was still churning out songs at a frenzied pace often releasing a new record every month But Kevin says Riley wasn't reliable He'd sign with one record label and while his contract was still in force he'd sign with another

15:28He'd often use different stage names or pseudonyms with different labels Hickey Free was one of the names I used Hickey Free Hickey Free For a time Riley was able to make it all work in part because he did have a little star power He'd done well with atomic power and later had another catchy tune titled Cowboy I've been

16:04a cowboy for all of my life I guess I like being free My horse my saddle and me Riley recorded it under the name Dixon Hall I looked out the window and I saw a thing called Hall's Clothing

16:34big sign and then Art Dixon came in and so I said well Dixon Hall that sounded okay This was how Riley operated He played Fast and Loose He also worked as an agent getting music labels to sign new artists You see I tell him what do you think a publisher is he's just a businessman

17:05he wouldn't know a hit song could crawl out from under his desk and beat him on the leg He sold songs to these executives with a combination of bluster and hype This role allowed Riley to capitalize on one of his greatest strengths He was a born salesman He once boasted that he could have started his own religion Read about Sioux City Sioux which was written by Dick Thomas Sioux City Sioux the day of the day Your hair is red

17:36Your eyes are blue I swapped my horse and dog Recorded by him on a small label and he brought it to me and I said if you do what I tell you you'll make a lot of money and he did I got him $7,000 advance and seven cents a copy the biggest money ever paid for a Hill Philly song in those days Riley was also a hustler in his personal life where the consequences

18:06of his actions were more serious Marion Kemenick knows this well she was adopted at birth as an adult she searched for and found her biological mother from her Marion learned that her father was Riley Shepard Marion's mother had met him while working as an actress in Chicago and she said he was very charming very good looking he played the guitar and he sang and I guess she was kind of smitten with him

18:37and uh she got pregnant that she told Marion wasn't supposed to happen he told her he was sterile and from what I understand he told every woman he was with that he was sterile whatever he'd achieved

19:08in the music industry it was all winding down by the early 1960s by then Riley had picked up and moved on to the west coast he first went to Oregon and then to California he told Kevin he gave up the music business so he could turn his attention to a new project an encyclopedia of folk music but Kevin thinks years of lying and cheating and breaking contracts

19:40had simply caught up with him he made it sound like he he did these moves for different purposes I think usually he was getting out of town before he was being tart and feathered guilty heart oh guilty heart it's perhaps fitting

Riley's Personal Life

19:58that the place Riley landed for the next chapter of his life was Hollywood Tinseltown was shiny and bright and full of the kind of transformative stories that Riley loved he arrived there with his common law wife and his young daughter Stasha for a while he thrived in his new role as Riley Shepard family man but like most things in Riley's life it didn't last your father is a crook after all these years

20:30Stasha still fixates on the memory of that old man's telephone call Stasha says it was a turning point in her relationship with her father that night she confronted him right when he walked in the door I was like you know screaming at him you're a crook you're a crook and he looked at me like he turned white and he was shocked

21:02and he argued we argued we fought I don't remember the exact words but I remember he stormed out and he went out to his car and he sat there and smoked and he didn't come back inside for a long time he would just that's what he would do when he was mad he would go out into his car and pout but the next morning Riley did what came naturally to him he turned on the charm he tried to smooth things over he made Stasha pancakes he told her the encyclopedia

21:32was going to make a lot of money and that his investors would get paid Stasha wanted to believe him well you know I loved my dad and he was very apologetic and sweet and you you want to believe your parents and also he was very good at convincing Stasha didn't know how much money her dad owed but she got the sense he was constantly evading creditors she tells one story of calling home

22:03to get a ride and when my dad picked up the phone he was pretending to be a Chinese man he was pretending to be used this accent that like from breakfast at Tiffany's that horrible you know was that Mickey Rooney anyway terrible but I knew it was him you know your father's voice I'm like dad and he was like hung up on me Riley took

22:34every shortcut he could to make a buck for a time he wrote porn under the pseudonym Zachary Quill one of his books glowing heat Stasha says her mother told her that Riley had worked out a formula she said oh well dad used to get all these cheap novels and then he would write porn scenes and he would have typists insert the porn scenes in these crappy novels

23:05and resell them this was Tasha's life things were always off kilter confusing she remembers another time when they had to flee their house before the landlord came probably because Riley hadn't paid the rent we got in this rickety old truck with all our stuff jammed in it and my father's encyclopedia of folk music was in there very carefully packed those were the

23:37biggest boxes that we took and all our other stuff was just kind of strewn in this truck and it wasn't very well packed and when we were driving down the highway I remember this it was so weird you know people were pointing at us and trying to get our attention and we were like I mean I remember my mother being like wow why are they waving at us and then realizing oh our stuff is flying out like our slim belongings that we had pared down from selling almost everything else those things were flying out

24:07not the encyclopedia of folk music but my clothes and what few things by the late 1970s the family had settled in Porterville California a town on the western edge of the Sierra Nevada mountains Riley spent his days working on his encyclopedia and to Stascha's mind swindling everyone he could it all ended when Stascha was 18 that year 1983 Riley Shepard did what he had done many times before

24:37he disappeared he told my mother who he had been with for whatever 23 years that he was taking a short trip to Los Angeles but when she woke up in the morning she realized that he had taken way more than what you would need for a short trip and he never he did not come back for more than a year Stascha had no idea where he was eventually she found him living about an hour away in Fresno

25:08they reconnected but everything had changed she now saw him for exactly who he was he glamorized the life of being a grifter he glamorized the life of being a con that's what I understand now that he he was a con man it's even hard to say that out loud he was though for years

25:39Stascha felt torn between her distaste for Riley's behavior and her love for the dad who made her smoke rings and took her to the Brown Derby by the mid-80s Stascha had left Porterville a few years later Riley returned to the town and played the role of the old cowboy musician Stascha mainly stayed in touch by phone as the years passed one day in 2008 she got a call her dad had taken a fall

26:10in his home and he ended up in the hospital after being alone on the floor for days and I called him and he goes honey I know I'm gonna die but he was so sweet I can't talk about that but he said he loved me and that he was proud of me it was like beautiful Riley rallied and moved to a nursing home when Stascha visited he seemed agitated

26:41and he goes you don't you don't know what it's like in here I thought he meant the nursing home because three beds the guy had the tv on it was loud I go what are you the nursing home he goes no you don't you don't know what it's like in here and here and he was pointing to his head and I go what what are you talking about he goes I'm I'm I'm flashing back on all the things I did and I did some bad things Stascha

27:13tried to comfort him but in retrospect she wishes she'd asked a question what bad things tell me about those what were the bad things maybe if you tell me about them you'll feel better because I'm wondering what what all he would have told me but he lived for a little bit in the nursing home that was the last time that I

27:56after Riley died Stascha had his body cremated for a long time she carried his ashes around with her she'd scatter a handful here or there which seemed fitting for a drifter there

28:35wasn't much in the Riley Shepard estate Stascha packed up some of his letters a cookbook he'd written for her and various other papers but his life's work the encyclopedia he'd been toiling over all those years he'd left that to someone else you're

Conclusion and Reflection

29:04listening to Hidden Brain I'm Shankar Vedanta

29:18Make Mother's Day even more special at Whole Foods Market kick off brunch or dinner with quality cheese and charcuterie with no synthetic nitrates then go seafood there's an abundance on sale at Whole Foods Market where it's all sustainable while caught or responsibly farmed at the bakery grab seasonal treats like their strawberry pretzel cream pie and you can't go wrong with a ready-to-heat quiche Lorraine deviled eggs and fresh-cut fruits to go celebrate mom with Whole Foods Market what would you

29:48like the power to do don't worry you got this whoa hear that I did it that's the sound of you helping your child find confidence that lasts a lifetime Bank of America invites kids 6 to 18 to join Golf With Us for a limited time sign them up for a free one-year membership giving them access to discounted tee times at thousands of courses as we champion the next generation who dares to ask what would you like the power to do restrictions apply activation required cbfa.com slash golf with us for complete details this is Hidden Brain

30:21I'm Shankar Vedant and in here we find row upon row of collection boxes on the shelves by the time I got

The Library of Congress Collection

30:31to the basement of the Library of Congress I figured I knew everything I needed to know about Raleigh Shepard he was a crook a con man a bad husband an unreliable father so as folklorist Steve Winnick pulls out the Richard Riley Shepard collection from the stacks I'm not holding my breath nobody's really used this collection very much so it's simply you know been there waiting for for you really up in his office Hagrid aka folklorist

31:02Steve Winnick spreads out the papers from the Richard Riley Shepard collection on a table he picks up a letter the date of this letter is September 7th 1976 more than

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