The Tale of the Cowboy Philosopher

2026-05-11 - source - Read full transcript

Shankar Vedantam (host)Stephen WinickStacya Shepard SilvermanKevin CoffeySteve EnsslinMarion KiminekRichard Riley Shepard

Key insights

A single-minded, decades-long obsession can be simultaneously a great quest and a great folly, and which one it is often cannot be judged until the person's life is over.

Vedantam frames Riley Shepard's 40-plus years spent hand-indexing an encyclopedia of American folk music as unresolvable: the same trait that made him a con man and absent father also produced a genuinely unprecedented scholarly artifact. He explicitly says we tend to judge obsessive people only by their outcome (Taj Mahal versus an unpublishable manuscript on the evil eye), when the process looks identical either way.

obsession-and-legacy

A person's public persona and private failures can both be true at once, and neither fully captures who they were.

Riley Shepard was, by turns, a talented singer with real hits, a serial con man who invented multiple aliases (Dickson Hall, Hicky Free, Zachary Quill and others), a father who staged elaborate lies (including a fake Chinese-accent phone bit to dodge his daughter), and a scholar attempting something 'almost nobody knows about,' per folklorist Stephen Winick. His daughter Stacya's view of him shifted repeatedly across her life as new evidence of each side surfaced.

deception-and-identity

Compulsive fabrication can extend even to false credit for other people's genuine achievements.

Riley told his daughter and others that he wrote 'Blue Christmas,' a song actually written by Billy Hayes and Jay Johnson and made famous by Elvis Presley. He also awarded himself invented credentials (a fake Ph.D. and D.D.) and lecture topics (God, man and science; the origin and growth of fascism) to bolster his self-styled 'Cowboy Philosopher' persona.

deception-and-identity

Major, genuinely novel scholarly work can be produced entirely outside institutional credentials and go almost completely unrecognized.

Riley had only a fifth-grade education, yet spent roughly two decades hand cross-indexing over 43,000 song titles down to 4,000 root songs, complete with musical notation, entirely from memory and without a computer. Folklorist Stephen Winick, who has studied folk song scholarship for years, says he had never heard of the project and calls the mere attempt significant to the field's history.

unrecognized-achievement

Institutional gatekeeping (in this case, the shift from paper to computerized documentation) can reject a body of work on economic grounds even when its scholarly value is recognized.

When Riley sought payment from the Library of Congress for his encyclopedia in 1979, the library acknowledged the scale of the work but couldn't afford to fund publication, especially given that 54 more volumes existed beyond the samples he'd sent. Winick frames Riley as 'an early casualty' of the transition from print to computer-based reference work.

unrecognized-achievement

Complex, unglamorous obsessive projects can act as a genuine bonding mechanism between unlikely collaborators.

Ted Ensslin, a retired insurance agent and former Porterville mayor, spent hours helping Riley collect and categorize entries for the encyclopedia and gave money to the project. His son Steve says the money 'doesn't mean anything' next to the enjoyment the collaboration brought his father, and Ted kept playing Riley's records in his office for years after Riley's death.

parent-child-relationships

Children of deceptive or unreliable parents often carry contradictory memories that don't resolve into a single simple verdict.

Stacya Shepard Silverman describes both cherished, almost magical childhood memories (cigar smoke rings, walks past Hollywood stars) and traumatic realizations (a creditor's call at age 12 revealing 'your father's a crook,' fleeing an apartment before the landlord arrived). She says she loved her father and also, eventually, had to acknowledge outright that he was a con man, holding both without fully reconciling them.

parent-child-relationships

A defensive habit formed in childhood in response to a parent's dysfunction can persist and shape unrelated adult behavior.

As a girl, Stacya became 'very militant' against the post office because her father blamed missing checks on lost mail, and she carried a residual anger at the postal service into adulthood, illustrating how a child absorbs and internalizes a parent's excuses as literal fact.

parent-child-relationships

The same trait of unwavering perseverance in obsessive people evokes both criticism and professional sympathy, depending on who is judging it.

Winick, himself a folklorist, says 'all scholars, and particularly folk song scholars, have something of the Riley Shepard in them,' distinguishing professionals only by the fact that they have lives that limit how much of themselves they can give to a single obsession, unlike Riley.

obsession-and-legacy

A once-scattered, undervalued body of work can eventually be preserved and made accessible even decades after its creator's death.

After the episode aired, hillbilly music fans organized to track down the dispersed boxes of Riley's encyclopedia (partly split up and sent to Nashville and the Buck Owens Museum), and Stacya delivered the recovered material to the Internet Archive, where it is now digitized and publicly available.

unrecognized-achievement

Media referenced

Blue Christmas - other - Song Riley Shepard falsely claimed to have written; Vedantam notes it was actually written by Billy Hayes and Jay Johnson and made famous by Elvis Presley.
Atomic Power - other - Riley's 1946 cover of a song inspired by the bombings of Hiroshima and Nagasaki; one of his few genuine hits.
Cowboy - other - A catchy Riley original, recorded under the pseudonym Dickson Hall, illustrating his habit of releasing under multiple names.
Sioux City Sue - other - Song by Dick Thomas that Riley, acting as an agent, helped place and profit from, described by Riley as the biggest money ever paid for a hillbilly song at the time.
The Research Project: Or, Folklore Without End - paper - Piece by anthropologist Arnold van Gennep about a scholar who dies at his library carrel still compiling references for an endless project on the evil eye; Winick invokes it as the closest parallel to Riley's encyclopedia.
My Unsung Hero - podcast - Hidden Brain's sister show, referenced in the credits as the source of the show's regular unsung-hero segment format.

Companies

Library of Congress - Riley corresponded with and eventually donated sample volumes of his folk music encyclopedia to the Library of Congress's American Folklife Center; folklorist Stephen Winick discovers the collection decades later.
Internet Archive - Post-episode update: fans located the scattered boxes of Riley's encyclopedia and Stacya delivered them to the Internet Archive in San Francisco, where the work is now digitized and online.
Buck Owens Museum - One of the places portions of Riley's encyclopedia pages were reportedly shipped after passing out of Ted Ensslin's hands.

Summary

Hidden Brain host Shankar Vedantam traces the strange, contradictory life of Richard Riley Shepard, a small-time con man and minor country-Western singer who spent more than 40 years secretly compiling an unprecedented encyclopedia of American folk music, entirely by hand and largely from memory. The episode opens with Vedantam descending into the Library of Congress stacks with folklorist Stephen Winick to examine a little-used collection donated decades earlier by a man Vedantam already believes he understands: a crook who died in 2009 leaving behind a trail of debts and broken relationships. What Vedantam finds complicates that picture entirely.

The first half of the episode, anchored by Riley's daughter Stacya Shepard Silverman, lays out the con man side of his legacy. Riley invented at least a dozen stage names and pseudonyms (Dickson Hall, Hicky Free, Zachary Quill among them), falsely claimed to have written "Blue Christmas," fabricated academic credentials for a self-styled lecture circuit as the "Cowboy Philosopher," told a girlfriend he was sterile to avoid responsibility for a child he later abandoned, and repeatedly evaded creditors and landlords. Stacya recounts a childhood of magical moments (cigar smoke rings, walks past Hollywood stars) shadowed by traumatic ones, including an elderly creditor calling their home when she was 12 to tell her "your father's a crook."

The episode's turn comes through music historian Kevin Coffey's recorded interview with Riley near the end of his life, and through Winick's discovery of Riley's Library of Congress correspondence. Riley had spent since 1960 hand-indexing more than 43,000 song titles down to roughly 4,000 root songs, cross-referencing versions, sources, and musical notation across some 200 years of American folk music, all without a computer and largely held in his own memory. Winick, who has studied folk song scholarship for years, says he'd never heard of the project and calls the sheer attempt significant to the field's history, even as he acknowledges the work was ultimately rejected for publication because the Library of Congress couldn't fund an undertaking of that scale.

A parallel thread follows Ted Ensslin, a retired Porterville insurance agent and former mayor who spent years helping Riley with the encyclopedia and gave him money along the way. Ted's son Steve says the money never mattered next to the enjoyment his father found in the collaboration, and that Ted kept playing Riley's old records for years after his friend's death. This relationship offers a counterweight to Stacya's more painful accounting, showing how the same obsessive, larger-than-life persona that hurt his family also genuinely enriched at least one friendship.

Vedantam closes by framing Riley's story as a parable about how uncertain the line is between a great quest and a great folly while the obsession is still underway, drawing a parallel to anthropologist Arnold van Gennep's essay about a scholar who dies at his library carrel still compiling an endless project on the evil eye. A postscript notes that after the episode first aired, fans helped track down the scattered boxes of Riley's encyclopedia, which Stacya then delivered to the Internet Archive, where the work is now digitized and publicly available.

Notable Quotes

"The story that is about to unfold before me is a story of obsession - its power, its beauty and its costs." - Shankar Vedantam

"I don't know if you are familiar with the anthropologist Arnold van Gennep... this man dies at his carrel in the library, and nobody quite remembers what he was doing there. And that's kind of the impression that you get of Riley Shepard." - Stephen Winick

"He glamorized the life of being a grifter. He glamorized the life of being a con man. 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." - Stacya Shepard Silverman

"The fact of the attempt I think is actually a significant fact in the history of folk song scholarship in the United States. And it's actually something almost nobody knows about." - Stephen Winick

"Trouble is you usually do not know whether an obsession is a great quest or a great folly until it's over." - Shankar Vedantam