Sidney E. Dickinson was the son of a Congregationalist minister, Charles H. Dickinson, and consequently he passed his childhood and youth in communities where his father had pastorates. He is known to have lived in Canandaigua, New York, from 1894 to 1901, in central Alabama, and in Fargo, North Dakota. He studied at the Art Students League under George Bridgman and William Merritt Chase (1910-11) and at the Academy school under Douglas Volk (1910-12). He then spent time traveling around the country, working in lumber camps, as a surveyor's rodman, and as a farmhand.
He made his debut in an Academy exhibition in the winter of 1915 with a self- portrait. In 1917, on the third appearance of his work in an Academy show, he received a Julius Hallgarten Prize. Over the course of the nearly fifty years he participated in Academy exhibitions, he received another Julius Hallgarten Prize (1924), the Isaac N. Maynard Prize (1933, 1938), the Benjamin Altman Prize (1936), and the Andrew Carnegie Prize (1942). From 1930 to 1933 Dickinson served on the Academy Council.
Although he produced many figure compositions, Dickinson was primarily a portraitist. Among his distinguished commissions were a series of individual portraits of the Rockefeller family, and the City of New York's official portrait of Mayor Fiorello H. La Guardia, executed in 1948. However, he seems also to have had a special place in his oeuvre for likenesses of his fellow artists: among those he chose to show at the Academy were portraits of Paul Arndt, Robert Aiken, Louis Bosa, Eugene Higgins, Hobart Nichols, Raphael Soyer, and in 1924 his second cousin, Edwin Dickinson.
Dickinson taught at the Art Students League in 1919-20 and led a life class at the Academy school (1928-31, 1939-43). He returned to the league to teach in the summers of 1943 and 1944 and then in 1949 became a regular league faculty member, remaining on staff until 1973. He maintained his studio in the Carnegie Hall building, just across Fifty-seventh Street from the league, until retiring to Windsor in the later 1970s.
