"Big Joe" Roberts, as he was known in vaudeville, toured the country with his first wife, Lillian Stuart Roberts as part of a rowdy act known as Roberts, Hays, and Roberts. Their signature routine was called "The Cowboy, the Swell and the Lady." At this time, in the first decade of the twentieth century, Buster Keaton's father, Joe Keaton, had started a summer Actors' Colony for vaudevillians between Lake Michigan and Muskegon Lake in Michigan. Roberts became acquainted with the Keaton family as a member of this community.

When Buster Keaton's film apprenticeship years with Roscoe "Fatty" Arbuckle came to an end, and Keaton began making his own shorts in 1920, he asked Roberts to join him. Roberts' hefty 6'3" frame, usually playing a menacing heavy or authority figure, made a striking and amusing contrast to the thin, 5'6" Keaton.