Dennis Burlingame traveled with the circus as a young man, taking any odd job that he could. He soon tired of a life constantly on the move, however, and left the circus to create murals and stage scenery for high schools. The artist Grant Wood discovered him painting ​“sweet, conventional” landscapes and encouraged him to create images inspired by his own experiences instead (Jewett, ​“Works of Olive Rush …” Chicago Daily Tribune, July 23, 1933). Burlingame participated in the New York branch of the Works Progress Administration during the 1930s, painting images inspired by the circus and his life in the city.