Shankar Vedantam

Soon, he told Kevin, he was getting gigs with hillbilly groups like the Dixie Reelers.

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, the cowboy philosopher.

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.

This is Tasha again.

A few years ago, she found one of the old flyers that advertised her dad's lectures.

The world traveler and philosopher was prepared to discuss a variety of important topics.

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.

He'd often use different stage names or pseudonyms with different labels.

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.

Riley recorded it under the name Dixon Hall.

This was how Riley operated.

He played fast and loose.

He also worked as an agent, getting music labels to sign new artists.

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.