Gregory Gillespie
American, 1936–2000
789 Followers
Because Gregory Gillespie’s style varied so widely, he refused identification with a movement or genre. Gillespie began his career as a realist, but over time embraced symbolism and Surrealism, at times touching geometric abstraction and assemblage. The unifying thread in his oeuvre was its trajectory, following loosely the narrative of his own life and particularly his progression from youth into middle age; his grand project was to mythologize his own life. Gillespie painted a number of self-portraits, bare-chested and blemished, and portraits of his wife, whom he sometimes depicted as Venus or Madonna. His still life paintings often suggested intimate facts about his life, featuring the likes of personal post cards and tantric figures.
Auction Results
Past Auctions
24 results
Self Portrait at 57, 1994
oil on wood panel
113.2 x 87.8 cm
Jun 24, 2025 • Bonhams
Self Portrait at 57, 1994
oil on wood panel
113.2 x 87.8 cm
Jun 24, 2025
Bonhams
Modern & Contemporary Art
Lot 45
Studio: Still Life, 1978
oil, graphite, charcoal, alkyd and paper collage on board
186.7 x 151.1 cm
Jul 17, 2024 • Christie's
Studio: Still Life, 1978
oil, graphite, charcoal, alkyd and paper collage on board
186.7 x 151.1 cm
Jul 17, 2024
Christie's
First Open | Post-War & Contemporary Art
Lot 191
Self-Portrait with Bread and Chakras, 1987
oil, graphite, wood and alkyd on panel
226.1 x 203.2 cm
Dec 14, 2022 • Christie's
Self-Portrait with Bread and Chakras, 1987
oil, graphite, wood and alkyd on panel
226.1 x 203.2 cm
Dec 14, 2022
Christie's
First Open | Post-War & Contemporary Art
Lot 270
Figures, 1976
oil on panel
30.5 x 52.1 cm
Dec 14, 2022 • Christie's
Figures, 1976
oil on panel
30.5 x 52.1 cm
Dec 14, 2022
Christie's
First Open | Post-War & Contemporary Art
Lot 271
Night Vegetation, 1973
oil on panel
15.2 x 12.7 cm
Dec 14, 2022 • Christie's
Night Vegetation, 1973
oil on panel
15.2 x 12.7 cm
Dec 14, 2022
Christie's
First Open | Post-War & Contemporary Art
Lot 272
Male Orgasm, 1999
Oil on panel
40.6 x 27.9 cm
Jun 20, 2019 • Swann
Male Orgasm, 1999
Oil on panel
40.6 x 27.9 cm
Jun 20, 2019
Swann • New York
The Pride Sale
Lot 257
Three figures in a landscape, 1960
oil on primed cotton
100 x 88 cm
Dec 2, 2016 • Leland Little Auction & Estate Sales
Three figures in a landscape, 1960
oil on primed cotton
100 x 88 cm
Dec 2, 2016
Leland Little Auction & Estate Sales • Hillsborough
The Winter Auction
Lot 226
Untitled, 1994
Oil on panel
65 x 60 cm
Sep 9, 2016 • Stair Auctioneers & Appraisers
Untitled, 1994
Oil on panel
65 x 60 cm
Sep 9, 2016
Stair Auctioneers & Appraisers • Hudson
Modern & Contemporary Exposition Auction
Lot 371
Split Image Swamp, 1999, 1999
oil on masonite
41.91 x 36.8 cm
Sep 19, 2014 • Skinner
Split Image Swamp, 1999, 1999
oil on masonite
41.91 x 36.8 cm
Sep 19, 2014
Skinner • Boston
American & European Works of Art
Lot 645
Untitled, 1936-2000
oil on board
48.3 x 43.2 cm
Jul 22, 2014 • Christie's
Untitled, 1936-2000
oil on board
48.3 x 43.2 cm
Jul 22, 2014
Christie's • New York, Rockefeller Center
Interiors
Lot 58
Still life with root vegetables, 1997
oil on clipboard
33.02 x 22.23 cm
May 17, 2013 • Skinner
Still life with root vegetables, 1997
oil on clipboard
33.02 x 22.23 cm
May 17, 2013
Skinner • Boston
American & European Works of Art
Lot 588
Split Image Swamp, 1999
oil on masonite
41.91 x 36.83 cm
Feb 1, 2013 • Skinner
Split Image Swamp, 1999
oil on masonite
41.91 x 36.83 cm
Feb 1, 2013
Skinner • Boston
American and European Works of Art
Lot 614
Untitled, Seated figure
oil and tempera on paper laid to cardboard
29.21 x 22.61 cm
Apr 17, 2012 • Doyle New York
Untitled, Seated figure
oil and tempera on paper laid to cardboard
29.21 x 22.61 cm
Apr 17, 2012
Doyle New York • New York
Doyle + Design
Lot 78
Seated Figure
Oil
29.3 x 22.5 cm
Nov 17, 2011 • Swann Galleries
Seated Figure
Oil
29.3 x 22.5 cm
Nov 17, 2011
Swann Galleries • New York
Sale 2262
Lot 29
Seated figure
oil, tempera and gouache with pencil on paper mounted on board
29.31 x 22.5 cm
Nov 17, 2011 • Swann Galleries
Seated figure
oil, tempera and gouache with pencil on paper mounted on board
29.31 x 22.5 cm
Nov 17, 2011
Swann Galleries • New York
American Art / Contemporary Art
Lot 29
Double image in Easthampton, Mass., studio, 1983
oil and alkyd with photo collage
56.52 x 52.71 cm
May 20, 2011 • Skinner
Double image in Easthampton, Mass., studio, 1983
oil and alkyd with photo collage
56.52 x 52.71 cm
May 20, 2011
Skinner • Boston
American & European Paintings & Prints
Lot 611
Male orgasm
tempera and oil on panel
50.32 x 35.26 cm
Nov 12, 2008 • Doyle New York
Male orgasm
tempera and oil on panel
50.32 x 35.26 cm
Nov 12, 2008
Doyle New York • New York
Modern and Contemporary Art and European and American Art
Lot 1198
Portrait of Randall Deihl, 1998
oil on panel
32.69 x 32.69 cm
Sep 12, 2008 • Skinner
Portrait of Randall Deihl, 1998
oil on panel
32.69 x 32.69 cm
Sep 12, 2008
Skinner • Boston
American & European Paintings & Prints
Lot 822
Portrait of a painter - dark painter, 1983
oil and alkyd on board
58.42 x 50.8 cm
May 15, 2001 • Christie's
Portrait of a painter - dark painter, 1983
oil and alkyd on board
58.42 x 50.8 cm
May 15, 2001
Christie's • East
Post-War & Contemporary Art
Lot 85
Interior with female nude, 1959
oil on board
30.48 x 40.64 cm
Mar 4, 1999 • Swann Galleries
Interior with female nude, 1959
oil on board
30.48 x 40.64 cm
Mar 4, 1999
Swann Galleries • New York
Prints, Drawings & Artist's Books
Lot 219
Peg in a beret, 1986
mixed media on panel
27.94 x 33.02 cm
Mar 13, 1998 • Skinner
Peg in a beret, 1986
mixed media on panel
27.94 x 33.02 cm
Mar 13, 1998
Skinner • Boston
American & European Paintings
Lot 416
Double image in Easthampton, Mass. studio
paintings
58.42 x 53.34 cm
Feb 12, 1991 • Sotheby's
Double image in Easthampton, Mass. studio
paintings
58.42 x 53.34 cm
Feb 12, 1991
Sotheby's • New York
Modern & Contemporary Paintings, Watercolours & Sculpture - Sale 1
Lot 483
The morbid man
oil on canvas
101.6 x 60.96 cm
Nov 6, 1990 • Christie's
The morbid man
oil on canvas
101.6 x 60.96 cm
Nov 6, 1990
Christie's • East
Contemporary Art Part III
Lot 127
Back to school, 1971
oil on paper
27.94 x 38.1 cm
Mar 11, 1988 • Christie's
Back to school, 1971
oil on paper
27.94 x 38.1 cm
Mar 11, 1988
Christie's • New York
19th/20th C American Paintings, Watercolours, Drawings and Sculptu
Lot 318


