Wooley was born in Erick, Oklahoma, and was reared on a farm. He learned how to ride horses at a young age, and was a working cowboy and rodeo rider. He also played in a country-western band. During World War II, Wooley was turned down for service because of his rodeo injuries. He worked in the oil industry and as a welder. In 1946, he moved to Fort Worth, Texas and became a country and western musician.
In the late 1950s, he embarked on a recording career, and recorded the song that made him famous. Wooley followed up "People Eater" with a series of lesser-known novelty hits. Wooley also wrote the theme song for the long-running television show Hee Haw.