In the 1930s, Comfort regularly worked as a commercial illustrator as well as a teacher at the Ontario College of Art and Design from 1935-1938. He subsequently held by a teaching position at the University of Toronto, a post he continued after the war until 1960. He taught primarily painting techniques, including mural-painting, and other studio courses later in his career at the university.
He was commissioned to design a mural for Toronto’s North American Life Building in 1932, the first in many he completed. The following year he met the American Precisionist Charles Sheeler. One of the artist’s most celebrated works, Tadoussac of 1935, suggests the influence of Sheeler due to its clear crisp colours and shapes.
Toronto Stock Exchange facade, with Comfort’s frieze
In 1936, Comfort rented a studio next to a room occupied by A. Y. Jackson, in the Studio Building, a warehouse made famous by the Group of Seven artists, and the following year he designed the frieze for the Toronto Stock Exchange. Comfort helped initiate Canada’s WWII War Art program and served as an official war artist in World War II, leaving an important body of work that records Canada’s war effort abroad. He was one of the organizers of the 1941 Kingston Conference, a meeting of Canadian artists to discuss the role of art in society as well as other issues facing the arts at the time. Furthermore, he was a founding member of the Federation of Canadian Artists and contributed to the 1951 Massey Report, which lead to the founding of the Canada Council. an organization that Comfort helped establish. In 1954 he was one of eighteen Canadian artists commissioned by the Canadian Pacific Railway to paint a mural for the interior of one of the new Park cars entering service on the new Canadian transcontinental train. Each the murals depicted a different national or provincial park; Comfort’s was Banff National Park.