[3] The following year Skinner saw his first record releases on Red Barn, a custom vanity label based in Chicago, Illinois, and Kansas City, Missouri.

After moving to Cincinnati, Ohio, Skinner met Lou Epstein, a former sales manager for King Records then operating his own label, Radio Artist.

Epstein signed the singer to a managerial and recording contract in 1949; a cover of Jimmy Work's "Tennessee Border" became Skinner's first chart hit.

Skinner's early sides have been cited as an influence on Johnny Cash, who covered his chain gang song "Doin' My Time" for Sun Records.

His late 1950s recordings of "What Makes a Man Wander", "Dark Hollow" and "I Found My Girl in the USA" reached the top 10 of the Billboard charts.