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Doubling as a theorist of literary character, Virginia Woolf was invested in the tribulations of the modern face, which she approached through the twin genres of portraiture and biography. This chapter revolves around Woolf’s staging of the modernist face in her novel Orlando: A Biography (1928). Woolf’s novel traces a change in the history of the physiognomic face in modernity – from Orlando’s memorable face-to-face with Queen Elizabeth in the early modern period to her search for meaning in the faces around her in London in 1928. At the same time, Woolf’s novel functions as a portrait of Vita Sackville-West, introducing a queer woman into the gallery of memorable historical characters, which Woolf visualized in relation to the all-male National Portrait Gallery in London. Through an engagement with Paul Mpagi Sepuya’s recent photographic reflections on Orlando, developed as a response to the racialized opening of the novel, the chapter frames modernist faciality’s mediation by racial difference.
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