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Lot Essay
Filled with rich symbolism and an electric tension, Dorothea Tanning’s 1944 painting Endgame is an extraordinary early masterpiece by the artist, in which she presents a bold, Surreal evocation of the final dramatic moments within a chess match. Across the square canvas, which mirrors almost exactly the dimensions of a traditional chess board, she uses the game as a site to explore and challenge traditional social mores and power dynamics. The composition focuses on the actions of a heeled, white silk slipper, representing the Queen, as she violently conquers the bejeweled black mitre of the Bishop, crushing it with a ferocity that causes blood to spurt from its base. In the upper right corner, four rooks lie on their sides, having already been removed from play by the Queen’s advances, while a zig-zagging, dotted line tracks her previous moves from square to square.
The title refers to the moment in a chess match when just a few pieces are left on the board and the tone of the game changes, as players assesses their position and the likely outcomes to victory. Unusually, the King is nowhere to be seen, leaving the Queen to control the play of action entirely through her own movements. No longer tasked with protecting the King, which in a normal game would remain her sole priority, she is able to plot the strategic defeat of her opponents independently, fully embracing her role as the most powerful piece on the board. Held in the same collection for over forty years, Endgame showcases the striking ingenuity and complexity of Tanning’s early Surrealist vision, which catapulted her to the forefront of the group’s activities in New York during the 1940s.
Born in Galesburg, Illinois, Tanning decided at the age of just seven that she would become a painter, and thereafter was determined to carve a different path beyond her family’s expectations for her to be a dutiful wife, mother, and churchgoer. Describing her hometown as a place where “nothing happened but the wallpaper,” she found an escape through Gothic novels and poetry, and at eighteen was deeply inspired by the works of Aubrey Beardsley, Gustav Flaubert and Théophile Gautier (quoted in “Dorothea Tanning: Exhibition Guide,” Tate, London, online; accessed 20 April 2025). Despite her parents’ opposition, she moved to Chicago to study fine art, and soon afterwards relocated to New York to continue her education, where she worked variously as an advertising illustrator, fashion model and a puppeteer. However, it was upon seeing Alfred H. Barr’s monumental exhibition Fantastic Art, Dada and Surrealism at The Museum of Modern Art in 1936 that Tanning reached a break-through in her painting—as she later explained, the show was “the real explosion, rocking me on my run-over heels. Here is the infinitely faceted world I must have been waiting for. Here is the limitless expanse of POSSIBILITY” (Between Lives: An Artist and Her World, New York, 2001, p. 49).
Wandering through the museum, she was captivated by the range of artworks on show, particularly those of Giorgio de Chirico, Marcel Duchamp, Salvador Dalí, Max Ernst, Francis Picabia, René Magritte, Leonor Fini, and Meret Oppenheim, which became “signposts, so imperious, so laden, so seductive and, yes, so perverse… they would possess me utterly” (ibid.). This experience opened up a rich, fantastical seam in her work, leading her to paint enigmatic self-portraits and compositions where young girls, exotic animals, and strange creatures met in bizarre encounters. Determined to meet the protagonists of the Surrealist movement for herself, Tanning set sail for Paris in the summer of 1939, her pockets filled with letters of introduction. However, the outbreak of the Second World War just a few weeks after her arrival brought a swift end to her explorations of the French avant-garde, forcing her to return home to the United States. Nevertheless, the influx of artists, writers, and gallerists to New York seeking refuge from the War over the ensuing years brought Tanning firmly into the city’s bourgeoning Surrealist circles, and she quickly immersed herself in their world.
On an ordinary day in late 1942, one such exiled artist entered her life—Max Ernst, scouting works for an upcoming exhibition dedicated to female artists at Peggy Guggenheim’s Art of This Century gallery, knocked on Tanning’s door and asked to see her most recent paintings. While in her modest studio, Ernst spotted a photograph of the artist playing chess, which was pinned to a small bulletin board. Recalling the meeting in her memoir, Tanning wrote: “Something else draws his attention then… ‘Ah, you play chess!’ He lifts the phrase like a question and then sets it down as fact, so that my yes is no more than an echo of some distant past exchange. ‘Then let’s have a game,’ pause, ‘that is, if you have time.’ We play. It has grown dark, stopped snowing. Utter silence pervades this room. My queen has been checked twice and is in very bad posture. Finally I lose. What else could I do under the circumstances? All thoughts of defense, counterattack and general strategy are crowded off the chessboard, and I see only the room with two pieces in it, my space challenged, my face burning. There is something voluptuous, close to the bone about chess. ‘Your game is promising. I could come back tomorrow, to give you some pointers…’ So the next day and the next saw us playing frantic chess. Calycine layers of an old husk, decorum, kept me sitting in the prim chair instead of starred on the bed. Until a week went by and he came to stay” (Birthday, Santa Monica, 1986, pp. 14-15).
This encounter marked the beginning of a love affair that would last for over three decades. Throughout their lives together, chess remained an important shared passion between the two artists, with numerous photographs through the years showing the pair mid-match. In Endgame, Tanning deploys the dynamic imagery of the game to somewhat unsettling ends, creating a dramatic and powerful composition that expresses her frustration with conventional bourgeois morality. As art historian and curator Alyce Mahon has noted, at the time she was working on Endgame, Tanning’s relationship with Ernst would have been seen as unconventional, and in some circles, scandalous. Both artists had been previously married—Tanning had divorced her first husband in 1943, while Ernst’s separation from his third wife, Peggy Guggenheim, was then in progress. As a result, they were unable to respectably live together in cosmopolitan art centers such as New York, without drawing negative attention. In choosing to have the Queen dominate and crush the Bishop, a symbol of the Church and by extensions traditional moral codes, Tanning may have been expressing her own desire to challenge and destroy the sense of propriety that ruled society at the time—indeed, Mahon has described the heeled slipper in Endgame as something of a self-portrait for the artist.
In the lower left corner of the composition, the chess board appears to rip and disintegrate, seemingly due to the force of the Queen’s actions—the checkered pattern creases in the space around where she pins the Bishop, creating the impression that the board is no longer firm and flat, as expected, but rather a flimsy, malleable material. As such, the world as she thought it to be—filled with rules, rigid expectations, and a set pattern of moves—is thrown asunder, as the Queen undermines its structural integrity and forces the grid to break. Through this tear, we catch a glimpse of a delicately painted, open landscape, stretching towards the horizon, suggesting another world beyond the board. The layers of rolling blue hills in the distance recall the setting of Tanning’s Self-Portrait from this same year (1944; San Francisco Museum of Modern Art), in which she portrays herself standing on the edge of a cliff, gazing out across a vast landscape of rock formations that recall the monumental scenery around Sedona in Arizona, where she had spent a blissful summer the year prior with Ernst. The memories of this sojourn had an important impact on Tanning’s work following their return to the East Coast—for example, another painting from 1944, Rapture, echoes the topography of the Verde Valley, south of Sedona. By including a similar landscape in Endgame, Tanning may have been invoking her own dream of escaping and leaving behind the New York art world, and returning to a place where she and Ernst had found happiness and freedom—revealing, as it were, the artist’s own strategic “endgame.”
Endgame made its public debut in the legendary exhibition The Imagery of Chess, which opened at the Julien Levy Gallery in New York in December 1944. Levy was a pioneering champion of Surrealism in America, showcasing the latest radical, avant-garde work from Europe through the 1930s, while simultaneously nurturing emerging talent, including Dorothea Tanning—Levy was the first dealer to take her on, and gave the artist her inaugural solo-exhibition in the fall of 1944. The concept for The Imagery of Chess exhibition had been born during a summer sojourn spent on the south shore of Long Island, where Levy and his wife, the artist Muriel Streeter, joined Tanning and Ernst in a rented beach house near Great River. All four were avid chess players, and were dismayed to find that there was not a proper chess set to be found anywhere in town. As a result, Ernst and Levy set about creating their own, utilizing a series of familiar objects they had discovered around the house—Levy reportedly used eggshells from breakfast as molds for his pieces, the rounded bottoms designed for use in the sand, while Ernst created assemblages using a host of empty containers and kitchen utensils.
The project sparked Levy’s imagination, leading him to conceive an exhibition devoted to the game, which opened at the end of the year at his gallery in midtown Manhattan. Informally curated by Marcel Duchamp, the show featured works by thirty-two leading contemporary artists, and included sculptures, drawings and paintings—as well as an exciting group of unorthodox playing sets—from the likes of Alexander Calder, Man Ray, Yves Tanguy, Kay Sage, Isamu Noguchi, Tanning and Ernst. Alongside the main exhibition, Levy organized an evening of chess in which invited guests were treated to a showcase game, as seven amateur players challenged the chess master George Koltanowski in a suite of simultaneous matches, all while Koltanowski was wearing a blindfold. Tanning was the only woman included in the event, taking her place in the line of challengers alongside Levy, Ernst, Alfred H. Barr, Xanti Schawinsky, Vittorio Rieti and Frederick Kiesler, with Duchamp acting as referee, calling out the moves to Koltanowski as they went along.
Endgame was acquired through Levy by the German Dada artist and filmmaker Hans Richter in 1949. Richter would later collaborate with Ernst and Tanning on his experimental film 8x8: A Chess Sonata in 8 Movements, in which one of the vignettes was based on an idea by Tanning, where the roles of King and Queen were performed by the couple. Endgame was last offered at auction in Levy’s estate sale in 1981, and has remained in the same collection for almost forty-five years.
The title refers to the moment in a chess match when just a few pieces are left on the board and the tone of the game changes, as players assesses their position and the likely outcomes to victory. Unusually, the King is nowhere to be seen, leaving the Queen to control the play of action entirely through her own movements. No longer tasked with protecting the King, which in a normal game would remain her sole priority, she is able to plot the strategic defeat of her opponents independently, fully embracing her role as the most powerful piece on the board. Held in the same collection for over forty years, Endgame showcases the striking ingenuity and complexity of Tanning’s early Surrealist vision, which catapulted her to the forefront of the group’s activities in New York during the 1940s.
Born in Galesburg, Illinois, Tanning decided at the age of just seven that she would become a painter, and thereafter was determined to carve a different path beyond her family’s expectations for her to be a dutiful wife, mother, and churchgoer. Describing her hometown as a place where “nothing happened but the wallpaper,” she found an escape through Gothic novels and poetry, and at eighteen was deeply inspired by the works of Aubrey Beardsley, Gustav Flaubert and Théophile Gautier (quoted in “Dorothea Tanning: Exhibition Guide,” Tate, London, online; accessed 20 April 2025). Despite her parents’ opposition, she moved to Chicago to study fine art, and soon afterwards relocated to New York to continue her education, where she worked variously as an advertising illustrator, fashion model and a puppeteer. However, it was upon seeing Alfred H. Barr’s monumental exhibition Fantastic Art, Dada and Surrealism at The Museum of Modern Art in 1936 that Tanning reached a break-through in her painting—as she later explained, the show was “the real explosion, rocking me on my run-over heels. Here is the infinitely faceted world I must have been waiting for. Here is the limitless expanse of POSSIBILITY” (Between Lives: An Artist and Her World, New York, 2001, p. 49).
Wandering through the museum, she was captivated by the range of artworks on show, particularly those of Giorgio de Chirico, Marcel Duchamp, Salvador Dalí, Max Ernst, Francis Picabia, René Magritte, Leonor Fini, and Meret Oppenheim, which became “signposts, so imperious, so laden, so seductive and, yes, so perverse… they would possess me utterly” (ibid.). This experience opened up a rich, fantastical seam in her work, leading her to paint enigmatic self-portraits and compositions where young girls, exotic animals, and strange creatures met in bizarre encounters. Determined to meet the protagonists of the Surrealist movement for herself, Tanning set sail for Paris in the summer of 1939, her pockets filled with letters of introduction. However, the outbreak of the Second World War just a few weeks after her arrival brought a swift end to her explorations of the French avant-garde, forcing her to return home to the United States. Nevertheless, the influx of artists, writers, and gallerists to New York seeking refuge from the War over the ensuing years brought Tanning firmly into the city’s bourgeoning Surrealist circles, and she quickly immersed herself in their world.
On an ordinary day in late 1942, one such exiled artist entered her life—Max Ernst, scouting works for an upcoming exhibition dedicated to female artists at Peggy Guggenheim’s Art of This Century gallery, knocked on Tanning’s door and asked to see her most recent paintings. While in her modest studio, Ernst spotted a photograph of the artist playing chess, which was pinned to a small bulletin board. Recalling the meeting in her memoir, Tanning wrote: “Something else draws his attention then… ‘Ah, you play chess!’ He lifts the phrase like a question and then sets it down as fact, so that my yes is no more than an echo of some distant past exchange. ‘Then let’s have a game,’ pause, ‘that is, if you have time.’ We play. It has grown dark, stopped snowing. Utter silence pervades this room. My queen has been checked twice and is in very bad posture. Finally I lose. What else could I do under the circumstances? All thoughts of defense, counterattack and general strategy are crowded off the chessboard, and I see only the room with two pieces in it, my space challenged, my face burning. There is something voluptuous, close to the bone about chess. ‘Your game is promising. I could come back tomorrow, to give you some pointers…’ So the next day and the next saw us playing frantic chess. Calycine layers of an old husk, decorum, kept me sitting in the prim chair instead of starred on the bed. Until a week went by and he came to stay” (Birthday, Santa Monica, 1986, pp. 14-15).
This encounter marked the beginning of a love affair that would last for over three decades. Throughout their lives together, chess remained an important shared passion between the two artists, with numerous photographs through the years showing the pair mid-match. In Endgame, Tanning deploys the dynamic imagery of the game to somewhat unsettling ends, creating a dramatic and powerful composition that expresses her frustration with conventional bourgeois morality. As art historian and curator Alyce Mahon has noted, at the time she was working on Endgame, Tanning’s relationship with Ernst would have been seen as unconventional, and in some circles, scandalous. Both artists had been previously married—Tanning had divorced her first husband in 1943, while Ernst’s separation from his third wife, Peggy Guggenheim, was then in progress. As a result, they were unable to respectably live together in cosmopolitan art centers such as New York, without drawing negative attention. In choosing to have the Queen dominate and crush the Bishop, a symbol of the Church and by extensions traditional moral codes, Tanning may have been expressing her own desire to challenge and destroy the sense of propriety that ruled society at the time—indeed, Mahon has described the heeled slipper in Endgame as something of a self-portrait for the artist.
In the lower left corner of the composition, the chess board appears to rip and disintegrate, seemingly due to the force of the Queen’s actions—the checkered pattern creases in the space around where she pins the Bishop, creating the impression that the board is no longer firm and flat, as expected, but rather a flimsy, malleable material. As such, the world as she thought it to be—filled with rules, rigid expectations, and a set pattern of moves—is thrown asunder, as the Queen undermines its structural integrity and forces the grid to break. Through this tear, we catch a glimpse of a delicately painted, open landscape, stretching towards the horizon, suggesting another world beyond the board. The layers of rolling blue hills in the distance recall the setting of Tanning’s Self-Portrait from this same year (1944; San Francisco Museum of Modern Art), in which she portrays herself standing on the edge of a cliff, gazing out across a vast landscape of rock formations that recall the monumental scenery around Sedona in Arizona, where she had spent a blissful summer the year prior with Ernst. The memories of this sojourn had an important impact on Tanning’s work following their return to the East Coast—for example, another painting from 1944, Rapture, echoes the topography of the Verde Valley, south of Sedona. By including a similar landscape in Endgame, Tanning may have been invoking her own dream of escaping and leaving behind the New York art world, and returning to a place where she and Ernst had found happiness and freedom—revealing, as it were, the artist’s own strategic “endgame.”
Endgame made its public debut in the legendary exhibition The Imagery of Chess, which opened at the Julien Levy Gallery in New York in December 1944. Levy was a pioneering champion of Surrealism in America, showcasing the latest radical, avant-garde work from Europe through the 1930s, while simultaneously nurturing emerging talent, including Dorothea Tanning—Levy was the first dealer to take her on, and gave the artist her inaugural solo-exhibition in the fall of 1944. The concept for The Imagery of Chess exhibition had been born during a summer sojourn spent on the south shore of Long Island, where Levy and his wife, the artist Muriel Streeter, joined Tanning and Ernst in a rented beach house near Great River. All four were avid chess players, and were dismayed to find that there was not a proper chess set to be found anywhere in town. As a result, Ernst and Levy set about creating their own, utilizing a series of familiar objects they had discovered around the house—Levy reportedly used eggshells from breakfast as molds for his pieces, the rounded bottoms designed for use in the sand, while Ernst created assemblages using a host of empty containers and kitchen utensils.
The project sparked Levy’s imagination, leading him to conceive an exhibition devoted to the game, which opened at the end of the year at his gallery in midtown Manhattan. Informally curated by Marcel Duchamp, the show featured works by thirty-two leading contemporary artists, and included sculptures, drawings and paintings—as well as an exciting group of unorthodox playing sets—from the likes of Alexander Calder, Man Ray, Yves Tanguy, Kay Sage, Isamu Noguchi, Tanning and Ernst. Alongside the main exhibition, Levy organized an evening of chess in which invited guests were treated to a showcase game, as seven amateur players challenged the chess master George Koltanowski in a suite of simultaneous matches, all while Koltanowski was wearing a blindfold. Tanning was the only woman included in the event, taking her place in the line of challengers alongside Levy, Ernst, Alfred H. Barr, Xanti Schawinsky, Vittorio Rieti and Frederick Kiesler, with Duchamp acting as referee, calling out the moves to Koltanowski as they went along.
Endgame was acquired through Levy by the German Dada artist and filmmaker Hans Richter in 1949. Richter would later collaborate with Ernst and Tanning on his experimental film 8x8: A Chess Sonata in 8 Movements, in which one of the vignettes was based on an idea by Tanning, where the roles of King and Queen were performed by the couple. Endgame was last offered at auction in Levy’s estate sale in 1981, and has remained in the same collection for almost forty-five years.