Following study at Cooper Union and the San Francisco Art Institute, in 1962 Gillespie went to Italy where he lived for the next eight years. The small, visionary landscapes and fantasies he did there incorporate elements of Flemish realism with touches of Surrealism, Italianate religiosity, and Germanic melancholia, and often depict figures engaged in disquieting confrontations. Gillespie describes the work of these years as "soaked with the textures of Italy–the feelings, the colors." These works combine traditional techniques (underpainting, glazing, and three-point perspective) with overpainted or partially scratched out collage elements in a way that enhances the ambiguity of the imagery. On his return to the United States in 1970 Gillespie began working from life. His recent still lifes, studies of landscape and vegetation, and self-portraits are meticulously painted, yet they also contain disturbing metaphysical presences that are consonant with Gillespie's Italian phase.
Virginia M. Mecklenburg Modern American Realism: The Sara Roby Foundation Collection (Washington, D.C.: Smithsonian Institution Press for the National Museum of American Art, 1987)
Gregory Gillespie knew little about art when he was at high school, but enjoyed drawing caricatures and pornographic cartoons for his friends. He attended Cooper Union in New York, intending to be a commercial artist, but fell in love with the reproductions of old-master paintings that he found in the library and decided to be a painter instead. He studied at the San Francisco Art Institute, and delivered newspapers in the mornings to support his wife and son. A fellowship led to eight years in Florence, where he created detailed paintings, photomontages, and assemblages inspired by everything he could “get my eyes on.” (Busa, “Art is a Form of Tantric Sex: Journals of Gregory Gillespie,” Provincetown Arts, 1997-98) Gillespie’s photorealistic images often incorporated found objects so that it is sometimes difficult to tell what is real and what is painted.