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Riley earned a BFA in painting form the Rhode Island School of Design, and a MFA in Sculpture from the Pratt Institute. He lives in Brooklyn, New York. He is noted for a body of work incorporating the seafarer's craft with nautical history, as well as the host of a legendary series of illegal clambakes on the Brooklyn waterfront for the New York artistic community. Riley told the Village Voice that he has "always been interested in the space where water meets land in the urban landscape.