Born in New York City in 1931, Cunningham grew up in Pittsfield, Massachusetts where he studied art with Ben Shahn. He graduated from Harvard College in 1953 and served as a lieutenant in the U.S. Marine Corps. He returned to New York and studied painting with Edwin Dickinson and drawing and anatomy with Robert Beverly Hale at the Art Students League, championing figurative painting and sculpture through the heights of Abstract Expressionism and Minimalism in New York. He taught for 18 years at the Brooklyn Museum School before co-founding the New Brooklyn School of Life Drawing, Painting and Sculpture with sculptor Barney Hodes in 1980. In 1983 he co-founded the New York Academy of Art.
