He served as a lieutenant in an air-warning squadron in the Pacific until the end of World War II, after which he returned to the University of Virginia.
In his first column on September 6, 1959, he inflamed the art establishment by proclaiming that Abstract Expressionism, the dominant style of the period, allowed "exceptional tolerance for incompetence and deception."
"[1] Other artists and critics, however, championed him as an honest and articulate observer of the art scene, which continued to provide ample targets for his barbed wit over the years.
In the 1940s and 1950s, under the pen name Matthew Head, Canaday wrote seven crime novels: The Smell of Money (1943), The Devil in the Bush (1945), The Accomplice (1949), The Cabinda Affair (1949), The Congo Venus (1950), Another Man's Life (1953), and Murder at the Flea Club (1955), each originally published by Simon & Schuster of New York.
Drawing in part on his experiences in the Congo, he set three of his mysteries in Africa, and they were heralded by one critic as subtly foreshadowing a time of change on the African continent.
In the 2014 film Big Eyes, directed by Tim Burton, Canaday is portrayed by actor Terence Stamp, making derogatory comments on the paintings of Margaret Keane.