Though Kenneth Callahan was born and later spent his adult life in Washington, he was raised in Glasgow, Montana. At the age of seven Callahan showed an inclination for art when he began painting the people and scenes around him. In 1926 Callahan and two other men barely made it to San Francisco in a beat-up Model T Ford. After a short period of homelessness, Callahan rented a room in a small building with a number of other artists and would continually paint on one canvas. To get out of San Francisco he got a job as a ship steward, but was kicked off the boat for fighting.
In 1930 he married Editor Margaret Bundy, and the Callahan home quickly became a popular place for the region’s close-knit community of artists. Dr. Richard Fuller sought out Callahan for his artwork and paid handsomely for a number of his paintings and offered him a job at the newly opened Seattle Art Museum. The 1950s proved to be a prolific time for Callahan, his paintings were included in two major New York shows, the popular Life magazine article “Mystic Painters of the Pacific Northwest” was released, and he was granted a Guggenheim fellowship. The 1960s proved to be more difficult, Callahan lost his wife and two years later his studio burned down. Though after he remarried in 1964 he was commissioned to design sets and costumes for a production of Macbeth and had major exhibitions in the Seattle area.