Woolery was born in Ashland, Kentucky and grew up an avid fisherman. He made his first foray into the entertainment business as a member of the band Avant-Garde with his partner Elkin "Bubba" Fowler. In 1968, Avant-Garde produced a moderate hit, Naturally Stoned (which inspired the name for the Woolery hosted Naturally Stoned on the Game Show Network).
At the urging of television host Merv Griffin, Woolery accepted hosting duties for newly created game show Wheel of Fortune in 1975. Combining strong looks with casual wit and unbounded charm, Woolery has since become one of the most respected and liked game show hosts in the business and has hosted hit shows Love Connection and Greed.
Woolery has his own line of motorized fishing lures, MotoLures.
Woolery had been married three times and has eight children. He lives in Utah.
See also: List of game show hosts