When Curly Ray was 15 years old, he, along with his cousin Ezra and brother Ned formed the Lonesome Pine Fiddlers around 1938.
The Lonesome Pine Fiddlers started off playing on radio station WHIS in the nearby town of Bluefield, where they remained until 1952.
[2] Although during this time Curly and brother Charlie Cline were also playing in Jimmy Martin's band, the Sunny Mountain Boys.
Occasionally, Curly Ray did studio work for many musicians such as Jimmy Martin, Bobby Osborne, Rex and Eleanor Parker and Hobo Jack Adkins.
"[3] While playing in Ralph Stanley's Clinch Mountain Boys, Curly Ray released a few solo, mostly instrumental, records.