Countless scholarly works have been devoted to the modernist movement and, more specifically, to Gertrude Stein's The Autobiography of Alice B. Toklas and Djuna Barnes's Nightwood. The notion of hybridity, however, has remained largely absent from published works about these texts. This project seeks to uncover hybrid elements from these two texts as well as determine some of the implications of their hybridity. I begin the analysis by exploring the links between Gloria Anzaldya's Borderlands, Adrienne Rich's "Compulsory Heterosexuality and Lesbian Existence," and Judith Butler's Gender Trouble. Together these three writers' theories offer a working definition of hybridity as a move or a strategy that seeks to create habitable spaces where boundaries of right and wrong, acceptable and unacceptable, are pushed aside. Tracing this overarching stance on hybridity through the Autobiography and Nightwood unveils hybrid texts drafted through the use of gender play, the refusal of compulsory heterosexuality, and literary innovation. From this stance, the Autobiography and Nightwood have renewed power to change literary history as well as the future, literary or otherwise.