His first political cartoons appeared during the 1896 presidential campaign but he preferred to concentrate on non-political subjects. At the end of his career he remarked that: "I always enjoyed drawing a type of cartoon which might be considered a sort of pictorial breakfast food. It had the cardinal asset of making the beginning of a day sunnier."
McCutcheon moved to the Chicago Tribune in 1903 and remained with this newspaper for 43 years. He made several overseas tours and provided drawings for the books Asia (1907) and Africa (1909). He also visited the Western Front during the First World War. In 1932 McCutcheon won the Pulitzer Prize for his coverage of the bank crisis.