Emmett Kelly’s work as a painter for a local carnival triggered his interest in clowns and the circus life. As a young man, he studied cartooning by correspondence. After finishing, he began entertaining school children by giving chalk talks where he used drawings to do presentations. In the early 1920s, while working as a painter for a commercial film company, he created the cartoon character of "Weary Willie" for the first time. Shortly thereafter, Kelly joined the circus full time.
Kelly worked in and around the circus at a number of jobs. He became a self-taught trapeze artist, and his skills landed him a job with Howe’s Great London Circus. Later, he was hired by the Sells-Floto and Hagenbeck-Wallace circuses where he worked until 1931. In the late 1930s, Kelly honed his skills as a pantomime while working with the Gertram Mills Circus. In 1937, he brought his cartoon character of Weary Willie, the down-and-out hobo, to life as a clown.
Weary Willie broke the clown mold by eschewing the familiar white face, red-spotted cheeks, ballooning suit and peaked hat of traditional performers. Kelly later called his hobo look the proudest achievement of his show business career. Weary Willie was a featured act of the Ringling Brothers & Barnum & Bailey Combined Circus from 1942 to the late 1950s.