Riddle first picked up a guitar when he was a boy living on a dairy farm in Ohio. As a teenager working in Kentucky coal mines, he continued playing and hooked up with local bluegrass artists and joined a band. After he started writing songs and developing his own blend of folk and country, Riddle joined a second band, C/R Express.
With a family to support, Riddle shifted away from music for a time, but after losing his mine job, he decided to try for a music career and traveled to Nashville. He talks about his Nashville experience in Part Three of "Country Boys," where he visits with Cody's guitar class and tells them, "You ever heard of Music Row where all the big stars play? I walked that street I don't know how many times. They got bars on the doors. They won't even talk to you."
But Riddle finally did get a break. He made a record, If You Can't Love a Woman, and it rose to number 11 on the Independent Country Charts.
Returning to Kentucky, Riddle became a mining preparation technician, but kept music an integral part of his life and built a studio that adjoins his house. Now retired from mine work, Riddle writes and records new music, some of which can be heard in "Country Boys." In the series, he also is a featured character; his daughter Jessica Riddle was Cody Perkins girlfriend throughout the filming, and in 2004 they were married.