[1] In 1914, he began work as a commercial artist at the newly established Brigdens commercial art branch office in Winnipeg established by Frederick Henry (Fred) Brigden, and by 1916 Comfort started attending evening classes at the Winnipeg School of Art.

Comfort saved money to attend the Art Students League of New York under Robert Henri and Euphrasius Tucker.

While in Toronto, Comfort joined the Arts and Letters Club, taking life-study classes and meeting members of the Group of Seven.

One of the artist's most celebrated works, Tadoussac of 1935, suggests the influence of Sheeler due to its clear crisp colours and shapes.

During this time he painted widely in the south of England before joining the 1 Canadian Infantry Division in Italy, travelling by sea in November 1943 with the field historian Samuel Hughes.

[10] His extensive involvement during his life with artists' organizations indicates his strong belief in the importance of art integrated with society.

1557 Colonel William Reginald Sawyer, Director of Studies 1948-1967 standing in front of the Mackenzie Building and the Stone Frigate in his academic robes for the Royal Military College of Canada.

After months of research and planning, Comfort decided to depict a hypothetical encounter between Captain George Vancouver and an unnamed Indian chief at a potlatch ceremony.

The wife of Governor General of Canada Roland Michener discovered the work after it was briefly misplaced and donated it to the University of British Columbia.

[13] Also in 1997, Edmonton-based artist Jane Ash Poitras painted a new mural representing the same scene with the intention to critique and re-negotiate Comfort's depiction of First Nations people.