Born Woodrow Wilson Sovine in Charleston, he was inspired by local radio musicians who told emotional stories in their songs. At first, Sovine struggled to find success and worked in a factory in Eleanor (Putnam County) while performing on the radio. After World War II, he focused fully on music, traveling through Alabama, Louisiana, and settling in Nashville.

He started recording in 1949 and joined the Grand Ole Opry in 1954. While he sang regular country songs, his biggest hits were story songs, particularly about truck drivers, such as "Giddyup Go," "Phantom 309," and "Teddy Bear." He kept performing until his death and was inducted into the West Virginia Music Hall of Fame in 2008.