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At the young age of 41, Gillespie was the subject of a major retrospective at the Hirshhorn Museum at the Smithsonian, a museum that would eventually own 14 of his paintings. Moving against a prevailing artistic climate that championed the abstract, he became known for meticulously painted figurative paintings, landscapes, and self portraits, His work often had a fantastical element, infusing the mundane with a complex and often contradictory spirituality. As Gillespie’s oeuvre continued to develop, his style became more diverse and he experimented with varied media, incorporating objects and photographs into his paintings.
Gillespie studied at the American Academy in Rome on a Chester Dale Fellowship from 1964 to 1970. From there he moved to Amherst, MA, where he became the mentor to a group of talented young artists that eventually became celebrated throughout the country as the NORTHAMPTON REALISTS.
Gillespie's work is in the permanent collections of the Metropolitan Museum of Art in New York, The Hirshhorn Museum and Sculpture Garden in Washington D. C., The National Museum of Art at the Smithsonian, The Whitney Museum of Art, and The Museum of Fine Arts in Boston to name just a few.
Watch video from the gallery talk by Robin Freedenfeld and Scott Prior on Gregory Gillespie.
 Self Portrait with Banana |
 Chair Seat Mandala |
 Common School Fair |
 Variation on Red Mountain |
 Lindesfarne |
 The Alchemist |
| "…the paintings are religious … because they come out of repression. They come out of a dramatic reaction to repression. They come out of the impulse to do sacrilege, which is a religious impulse." | ||
 Self Portrait on Steps with Fran |
 Portrait of Rich Michelson |
 Self Portrait Triumphant |
 Self Portrait Cutout |
 Self Portrait with Glasses |
 Self Portrait (Angry) |
 Double Sided Mandala |
 Tiny Landscape |
 Inhabited Landscape |
 English Landscape with Peggy and Judy |
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| "For me the painting is not a success unless (it is) something really solid and substantial. From ten feet it looks solid and three dimensional – from five feet you begin to doubt it, and close up you get completely lost in the beauty of another illusion that refers to the microscopic and, perhaps, somehow the spiritual." | ||
 Self Portrait Head |
 Peggy and Blue Figure |
 Circle Goddess Study |
 Abstract Cityscape |
 Face |
 Peter Cooper |
 Seated Figure |
 Woman on Chair |
 Couple with Dog |
| "It’s a living thing, painting. It’s a living process. It’s anthropomorphic. It’s a sort of identification, a kind of wound, and if I’m painting the inside of a wound it feels different than if I were painting on the surface of some other thing. It’s a very intuitive, emotional process." | ||
 Inverted Figure |
 Manic Depression |
 Figure |
 Lady with Necklace |
 Steve Stamos |
 Self Portrait with Green |
Printwork: |
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 Grandmother |
 The Orange Plant |
 The Baptism |
 Cafe |
 Two Figures |
 Gathering |
 The Kiss |
 The Garden at Dusk |
 Mother and Son |
| "The need in making art is to find out how to enlist the support of the dormant genius-self who plays only when the conscious, pragmatic mind relaxes its need to control everything, its tendency to squeeze the life out of everything. I’ve got to figure out ways to open its grip so that surprises can happen." |  Self Portrait Lithograph |
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Gallery talk by Robin Freedenfeld
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News Articles: |
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| The New York Times: Gregory Gillespie, 64, an Unflinching Painter By Roberta Smith, April 29, 2000 Finding the Reality That Lies Just Beyond the Real By Miles Unger, October 31, 1999 |
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