This project engages Antonin Artaud's highly influential critical volume, The Theater and Its Double, through the dual critical lenses of Psychoanalysis and Deconstruction in order to generate responses to questions posed by Artaud’s hybrid text of philosophy, literary criticism, and theatrical manifestos. In his performative writing, Artaud invites readers to inquire into and engage with what he means by “Theater's Double.” With this inquiry as a foundation, this dissertation engages theories of the self and its narrative-making nature, the self and the instability of memory, and the self in its capacity to express truths through the performance that is writing. Therefore, this project is partly devoted to renewed analyses of Artaudian concepts and images of thought, mapping these analyses onto the work of Modern and late Modern playwrights as it engages conceptual complications of doubles and doubling as they appear as important emblems in Modern and late Modern dramatic works. This dissertation ultimately traces a lineage for understanding conceptions of doubles and doubling through a theoretical engagement with the work of Otto Rank, Sigmund Freud, Jacques Lacan, and their interpreters. In doing so, this project ultimately reconceives binary oppositions between philosophical and literary theoretical writing as itself a kind of double, and so confronts the oppositions between Representation (in the so-called “Psychological Theater”) vs. Manifestation of Affects, or the “Theater Equal to Life” that Herbert Blau describes, as well as the binary opposition between and the doubleness of Violent Spectacle and Cathartic Tragedy. To this end, this dissertation engages and re-assesses classic Psychoanalytic literature on doppelgängers, shadows, effigies, and mirrored, reflected, and photographed images, and extends this field of thought to conceptions of the uncanny as originally conceived by Sigmund Freud. Artaud’s conceptions of cruelty are likewise re-assessed through these conceptions of doubles and doubling, the analysis complicated by locating these conceptions in the dramatic works of Sara Kane, Amiri Baraka, and Samuel Beckett. This research thus renews the importance of Antonin Artaud’s writing for theater and performance studies beyond theatrical-aesthetic precepts and renews the critical importance of Modern psychoanalytical texts and theory, finally suggesting a new confluence of Psychoanalysis and Performance theory that complicates the stability of the self and its narrative-making.