Painted in 1957, Oreste e Pilade is a rare and evocative example of de Chirico’s late production. Born in Greece from Italian parents, de Chirico was surrounded by images of the antique world since early childhood. Classical mythology, history, art and architecture provided an endless source of inspiration for the painter, who often combined these subjects with a contemporary setting. Oreste e Pilade is an outstanding example of a theme that de Chirico would revisit during his career. The subject of this work is taken from Homer's The Odyssey, the vengeful tale of Orestes and Pylades. After the discovery of his mother’s illustrious affair, Orestes was sent to live with his cousin Pylades. The boys grew up as brothers and upon hearing the news that Orestes’s mother, Clytemnestra, had murdered his father Agamemnon, the boys sought and eventually exacted revenge against Clytemnestra and her lover, Aegisthus. The characters here are shown as two faceless, mannequin heads. De Chirico had first introduced mannequins into his painting in 1914, the faceless, inanimate mannequins act as a substitute for a real, human presence and are placed within often enigmatic, melancholic settings, creating compellingly disquieting and Surreal visions.

Ardengo Soffici, de Chirico's first Italian critic, observed: "The painting of de Chirico is not painting, in the sense that we use that word today. It could be defined as a writing down of dreams. By means of almost infinite rows of arches and facades, he truly succeeds in expressing that sensation of vastness, of solitude, of immobility, of stasis which certain sights reflected by the state of memory sometimes produce in our mind, just at the point of sleep. Giorgio de Chirico expresses as no one else has ever done the poignant melancholy of the close of a beautiful day in an old Italian city where, at the back of a lonely piazza, beyond the setting of loggias, porticoes, and monuments to the past, a train chugs, the delivery van of a large department store is parked, or a soaring factory chimney sends smoke into the cloudless sky" (Ardengo Soffici, De Chirico e Savinio, quoted in Joan M. Lukach, "De Chirico and Italian Art Theory, 1915-1920" in De Chirico (exhibition catalogue), Museum of Modern Art, New York, 1982, p. 37).