Playwright Eugene O'Neill's expressionistic text-based approach to The Emperor Jones, with an emphasis on fixity, was at odds with African American actor Charles Gilpin's improvisational performance technique, stressing rupture, spontaneity, and discontinuity. The contemporary avant-garde performance troupe The Wooster Group likewise produces subversive and interrogative forms of identity in performing the play, which challenge the normative approach to gender, race, and an imagined orientation. The historical foundation of subversion and destabilization laid by O'Neill and Gilpin were manifold in the Wooster Group's production of The Emperor Jones, and not only formed a backdrop to it but also played a central role in the group's representation of race and even gender on the stage. In this essay, I use O'Neill's play, The Emperor Jones, a crucial example of racialized fantasies of identification, to explore how the modernist stage through the performances of Gilpin and The Wooster Group constructed racialized subjects of both its performers and audiences. Gilpin and the Wooster Group's strategies each shared a similar complexity in the portrayal of black identity in performance. Offering an examination of how ideologies of race and gender overlap in The Emperor Jones, I hope to show how each performance signifies a range of subversions and differences simultaneously and sometimes oppositionally that needs to be explored both holistically and in detail to offer a fuller picture of these remarkable attempts. Through this approach, I examine Gilpin's creative adaptations of O'Neill's text and illuminate how it is that the Wooster Group's appropriative use of blackface in their performance has come to gain critical acceptance.