Randall began his career as a supporting actor and foil at RKO, but he left when Monogram Pictures promised him the chance to star in films. They were true to their word, and he appeared in a series of Western films through the 1930s and 1940s. (In 1935, he actually played a star of Westerns in RKO's "Another Face", released in 1935.) Many of Randall's early B-movies with Monogram feature him as a singing cowboy, but his later roles were generally straight Western stories, and all were hampered by the low budgets typical of that studio. Many of his cowboy characters were named "Jack". His older brother Robert Livingston (born Robert Edward Randall) was also an actor in Western films of the time.