Singing cowboy Sky continues the tradition of the singing cowboy today. Singing cowboy A singing cowboy was a subtype of the archetypal cowboy hero of early Western films, popularized by many of the B-movies of the 1930s and 1940s. The typical singing cowboys were white-hat-wearing, clean-shaven heroes with the habit of showing their emotions in song. Around the campfire, 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. While much of what is included in the genre of "cowboy music" is "traditional",
The Cadillacs group's first recording came in July 1954, with Josie Records #765, featuring "Gloria" and "Wonder Why." In 1955, Willingham and Clark left the group and were replaced by Earl Wade and Charles Brooks. At this time, the group first began to experiment with choreography, suggested by manager Esther Navarro. Later that year came the group's biggest hit, "Speedoo", Carroll's nickname. Lavern Drake left the group in 1956 and was replaced by J. R. Bailey. That same year the Cadillacs released a doo-wop version of Rudolph the Red-Nosed Reindeer that peaked at No. 11 on "Billboard" magazine's Rhythm & Blues Records