Pickens worked as a rodeo star before landing his first movie role in the western Rocky Mountain (1950). His numerous appearances playing a cowboy, of both the villainous and the comic sort, include Old Oklahoma Plains (1952), Down Laredo Way (1953), and Blazing Saddles (1974). He also played the pilot who waved his cowboy hat while guiding the nuclear bomb to its destination in Dr. Strangelove (1964).