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Much of Prestopino’s work was in the vein of social realism. During the 1940s and 1950s he became deeply invested in portraying everyday Manhattan and Harlem scenes. He first became interested in the Ashcan school at the National Academy of Design, and remained committed to an interest in working with urban scenes. His lively treatment of people and events revealed his affinity for sixteenth-century artist Pieter Breughel. Later in his career, he focused on producing images of nudes and picturesque New Hampshire