Wooley was born in Erick, Oklahoma and grew up on a farm. He learned how to ride horses at a young age, and was working cowboy and rodeo rider. He also played in a country-western band. During WWII, 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.
Wooley appeared in dozens of western films from the 1950s through 1970s, most notably High Noon. He also appeared in The Outlaw Josey Wales and Giant. He also co-starred in the TV Western Rawhide.
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".
He was a regular on Hee Haw as the drunken country songwriter Ben Colder. The Colder persona became popular and he released music and performed under that name as well as his own.
Wooley continued occasional television and film appearances through the 1990s. In 1996 he was diagnosed with leukemia, and succumbed to the disease at the Skyline Medical Center in Nashville, Tennessee.