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This chapter frames the collaboration between Gertrude Stein and Pablo Picasso in the making of the 1906 portrait of Stein as a struggle over the modernist representation of the face. Having started the portrait with the sitter in front of him, Picasso famously erased Stein’s likeness and subsequently replaced it with a mask. Stein self-styled herself as an author and celebrity using Picasso’s portrait as a prop – as if it were a photograph. In turn, Stein’s literary portraits of Picasso attest to a desire for a radical erasure of the face, from memory and representation alike. The face nonetheless returns in the invocation of the proper name Picasso and through the intermedial dimensions of Stein’s portraiture writing. The chapter concludes by revisiting Nella Larsen’s use of the mask, specifically as the mask of whiteness, in her novel Passing (1929), a re-writing of Stein and Picasso’s experimentation with the racial dynamics of the mask.
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