As a teenager, Sheb formed his own band. In the mid-1940s, he performed on radio stations WLAC and WSM in Nashville, Tennessee, and subsequently had his own show on the Calumet Radio Network. He signed to the Bullet Records Label in 1946, moving in 1948 to MGM Records where he remained until 1973.
In 1958 he released his most famous hit the novelty tune, “The Purple People Eater.” The song went No. 1 on the pop charts and stayed there for six weeks. “That’s My Pa,” another novelty effort in 1962, was his first country hit. It also reached No. 1. As Ben Colder, Wooley scored six country and five pop hits with such parodies as 'Don’t Go Near the Eskimos' 'Still No. 2,' 'Almost Persuaded No. 2,' 'Detroit City No. 2' and 'Harper Valley P.T.A.”'His last charted country song came in 1971 with 'Fifteen Beers Ago,' a sendup of Conway Twitty’s 'Fifteen Years Ago.'
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