"Smiley" Wilson was born Hamilton K. Wilson in Etowah County, Alabama, and attended school near Gadsden, Alabama. At 17, he was a member of Tex Bynum's Rogers County Cowboys, and later worked for two years with Gene Durnel's Rio Grande Rangers. In 1947, Wilson was appearing on WBXL radio in Peoria, Illinois, and cutting records for the Apollo label. By 1949, Wilson was leading his own band, the Range Partners, based at WRAL in Raleigh, North Carolina, and also appearing on the Louisiana Hayride out of Shreveport. Wilson recorded the song "Juke Box Boogie," a hot piece of early rockabilly, in 1950, which was licensed by Ivin Ballen for his Gotham label but never issued. He also managed an appearance in the movie Square Dance Jubilee, produced by Robert L. Lippert and directed by Paul Landres (Go Johnny Go), also featuring Spade Cooley, Cowboy Copas, and The Tumbleweed Tumblers, in 1949. Wilson also played with the Circle 3 Ranch Gang.