This dissertation addresses and hopes to complicate the reception history of modernist literary productions as wholly positive reactions to Freudian psychoanalysis. Through close readings of fictional, poetic, epistolary, and expository texts, historical analysis, and an examination of the iterative development of psychoanalytic and other critical theories, these chapters expose a much more complicated counter-narrative of mutual resistance and ambivalence between the discourses of psychoanalysis and Anglo-American literary modernism. This dissertation presents a methodological intervention into the use of the concept of transference outside of the clinical scene in literary criticism, followed by a theoretical history of the figure of resistance in the elaboration of psychoanalytic epistemology in the first chapter. The four subsequent chapters present a series of modernist case-histories of resistance to psychoanalysis, examining respectively the discursive encounters of Otto Gross, D.H. Lawrence, Wyndham Lewis, and Mina Loy with psychoanalytic theory and clinical practice, which produced textual mode of address that this project refers to as obloquies of resistance. The dissertation also tracks an alternative history of clinical practice by foregrounding the relationship of these literary authors to a group of analysts at odds with the burgeoning psychoanalytic institution, including Carl Jung, Sándor Ferenczi, Trigant Burrow, Barbara Low, and Roberto Assagioli. The project closes with the suggestion that Gilles Deleuze and Félix Guattari were informed by these modernist interventions, and that the rubric of repudiative obloquy can give new insights into the poststructural and postcolonial projects that criticize psychoanalysis.