The Cowboy Philosopher

The story of Riley Shepard centers on a man who lived between deception and an extraordinary, solitary effort to catalog American folk music. Over decades he lied to family, investors, and business partners, yet he also produced an ambitious index of songs that scholars later recognized as a significant achievement. The tension between his cons and his private labor forms the core of the episode.

A Life of Hustle and Music

Riley Shepard was born in 1918 on a North Carolina farm and left school after fifth grade. He moved through minstrel shows and hillbilly groups in the 1930s, then reached Chicago in the early 1940s. There he recorded under several names, including Dixon Hall and Hickey Free, and released songs such as “Atomic Power.” He cultivated the persona of the “cowboy philosopher,” grew a mustache, and pitched himself as a lecturer on history and world affairs. He also worked as a song promoter and agent, securing advances for other writers while signing conflicting contracts himself. By the early 1960s he had relocated to California, where his musical career largely ended.

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