James Clarence Wakely was an American actor, songwriter, country music vocalist, and one of the last singing cowboys. During the 1930s, 1940s and 1950s, he released records, appeared in several B-Western movies with most of the major studios, appeared on radio and television and even had his own series of comic books. His duet singles with Margaret Whiting from 1949 until 1951, produced a string of top seven hits, including 1949's number one hit on the US country chart and pop music chart, "Slippin' Around". Wakely owned two music publishing companies in later years, and performed at the Grand Ole Opry until shortly before his death.

A singing cowboy was a subtype of the archetypal cowboy hero of early Western films. It references real-world campfire side ballads in the American frontier, the original cowboys sang of life on the trail with all the challenges, hardships, and dangers encountered while pushing cattle for miles up the trails and across the prairies. This continues with modern vaquero traditions and within the genre of Western music, and its related New Mexico, Red Dirt, Tejano, and Texas country music styles. A number of songs have been written and made famous by groups like the Sons of the Pioneers and Riders in the Sky and individual performers such as Marty Robbins, Gene Autry, Roy Rogers, Tex Ritter, Bob Baker and other "singing cowboys". Singing in the wrangler style, these entertainers have served to preserve the cowboy as a unique American hero.