Building on previous comparisons between Gertrude Stein’s literary work and early modernist artwork, this interartistic study offers an in-depth examination of the structural and conceptual connections between Stein’s literary portraits and portraits created by Cezanne, Matisse and Picasso. These portraits reveal a continuing search for a means of portraying the Self, an incessant questioning of the Self - both in terms of identity and entity - and a relentless reflection on creating the Self anew in art. In the process of searching, Stein, Cezanne, Matisse and Picasso came to create portraits of the 20th century Self.