Shoemaker started his career at the Chicago Daily News and spent 22 years there. His 1938 Pulitzer cartoon for the paper was "The Road Back", featuring a World War I soldier marching back to war. The 1947 winning cartoon for the paper was "Still Racing His Shadow", featuring "new wage demands" of workers trying to outrun his shadow "cost of living". He went on to work for the New York Herald Tribune, the Chicago American, and Chicago Today. By his 1972 retirement he had drawn over 14,000 cartoons.