Awarded Comedian of the Year by the Country Music Association in 1968.
Formed his own radio band, The Plainview Melody Boys, at the age 15.
He got the idea for his hit song, Purple People Eater, when a friend of his mentioned that his young son came home from elementary school with a joke he had heard: "What has one eye, one horn, flies and eats people?" "A one-eyed, one-horned flying people eater!".
His wife Linda was also his manager.
In 1969 Wooley was one of the original members of the cast of "Hee Haw" (1969), the-long running country slapstick series. He also wrote the familiar theme song. He left the show after only filming 13 episodes due to other professional demands. He returned from time to time as a guest.
It is believed that he may be the person who recorded the famous Wilhelm Scream for the movie Distant Drums (1951). He was one of the few actors assembled for the recording of additional vocal elements for the film. It is very likely he was asked on the spot to perform other things for the film, including the screams for a "man getting bit by an alligator" (as the Wilhelm Scream takes were slated).
The running lyric to Sheb's huge novelty song hit went like this: "It was a one-eyed, one-horned, flying purple people eater." It spent six weeks at No. 1 and sold 3 million copies in 1958. Other silly songs included "Talk Back Blubbering Lips," "Sunday Morning Fallin' Down," "Harper Valley PTA (Later That Same Day)," "The Happiest Squirrel in the Whole U.S.A." and "Fifteen Beers Ago." He also recorded the parody "Don't Go Near the Eskimos," based on Rex Allen's 1962 hit "Don't Go Near the Indians.".
Was one of the four gunslingers who stalked Gary Cooper in the western film classic High Noon (1952) (for the record, the others were Ian MacDonald, Robert J. Wilke, Lee Van Cleef).