Wooley's big break professionally came when he was cast as the drover Pete Nolan in the CBS western Rawhide (1959–1966) with Eric Fleming, Clint Eastwood, and Paul Brinegar. During that time Sheb also wrote and directed some of the episodes. He also continued to act in major films, including Giant, The Outlaw Josey Wales, Silverado, and in Hoosiers starring Gene Hackman, Barbara Hershey, and Dennis Hopper. In the latter film, Wooley portrayed Hackman's longtime friend, Cletus Summers, the principal of Hickory High School.