As an actor, he portrayed Cletus Summers, the principal of Hickory High School and assistant coach in the 1986 film Hoosiers; Ben Miller, brother of Frank Miller in the film High Noon; Travis Cobb in The Outlaw Josey Wales and scout Pete Nolan in the television series Rawhide.

Wooley is also credited as the voice actor who provided the Wilhelm scream and all of the other stock sound effects for Thomas J. Valentino's Major record label during the 1940s.

When the United States entered World War II, Wooley tried to enlist in the military but was unsuccessful due to his numerous rodeo injuries.

In 1946 he moved to Fort Worth, Texas, where he earned a living as a country-western musician recording songs and traveling for three years with a band throughout the South and Southwest.

[5] In Fort Worth he also married for the second time, to Edna Talbott Bunt, a young widow with an infant son named Gary.

[6] The three of them left Texas in 1950 and moved to Hollywood, where Wooley hoped to establish himself as an actor or singer in film or in the rapidly expanding medium of television.

[5] At the age of 15, with a talent for music, Wooley formed a band called the "Plainview Melody Boys", that periodically performed on radio at station KASA in Elk City, Oklahoma.

[1] At the start of the 1950s, Wooley began fusing Western swing with rhythm and blues, but later in his career his music would shift to the more commercial Nashville sound.

[8][9] In the United Kingdom, he enjoyed a minor hit with the comedy single "Luke the Spook" on the flip side of "My Only Treasure", a ballad in the country and western tradition.

He portrayed Bill Bronson on The Cisco Kid, Harry Runyon in "The Unmasking" on My Friend Flicka, and Shev Jones in "The Iron Trail" on Cheyenne.

He was in Rocky Mountain (1950), and he portrayed outlaw Ben Miller in High Noon (1952) and Baxter in Terror in a Texas Town (1958).

[19] Wooley was the recipient of numerous awards over the years for his accomplishments as a singer, actor, and writer for both comedic and dramatic productions.