As a youth, Willard dropped out of several schools. In addition to jobs at county fairs, he worked in a mental institution. In 1909, he moved with his family to Chicago. He went to Union Academy, where he illustrated the Reflector yearbook in 1912. After attending the Academy of Fine Arts in Chicago in 1913, he was a cartoonist with the Chicago Herald (1914–18), where he drew the Sunday comic strips Tom, Dick and Harry and Mister and Mrs. Pippen/Mrs. Pippin's Husband and a daily comic strip which used various titles. At the Herald, he got to know cartoonists E. C. Segar and Billy DeBeck, of Popeye and Barney Google fame respectively.
