Rob Diebboll is the son of artists. His father, also Robert Diebboll, was a well-known potter who established Pines End Pottery in Washington, Michigan. Diebboll the younger grew up in Michigan before relocating to Massachusetts. He now lives and works full time in Rockport, Massachusetts.
Cape Ann, on Boston's North Shore, has always inspired artists and Diebboll is no exception. Some of the artists that summered in Gloucester and Rockport are influences on his work, most important among them is Milton Avery. Although Fairfield Porter spent his summers in Maine, the colors and atmosphere of Diebboll's paintings have much in common with Porter's work.