This dissertation explores the grounding of Lacanian psychoanalysis in the intellectual and artistic movements of the modernist period, and reads masculine anxiety in the modernist novel in terms of Lacan's work on psychosis, masochism, and narcissism. The thrust of my dissertation is twofold. The first half aims at a reinterpretation of Jacques Lacan's work in light of his early intellectual engagements with Freud, G. G. de Clerambault, and Heidegger, and as such establishes the basis for Lacan's early work in the traditions of Freudian dream analysis, experimental French psychiatry, and existential phenomenology. The second half, starting with a discussion of Lacan's third seminar, The Psychoses, and D. P. Schreber's Memoirs of My Nervous Illness, examines Henry James's enigmatic 1901 novella The Sacred Fount as a meditation on the uniquely masculine anxiety over negotiating same-sex intellectual relationships, manifested as psychosis. The subsequent chapters on Proust, Sacher-Masoch, and Joyce, read with the later Lacan of Seminars XX and available sections of XXIII, explore and flesh out possible Lacanian readings of masochism and narcissism with regard to paternal (or pseudo-paternal) relationships. The major theme of my dissertation is that of vexed intellectual relationships between men separated by generational difference. Situating Lacan's discourse in the context of the modernist period, I illustrate how Lacan's intellectual apprenticeships and encounters (real and imagined) play out in his mature work, beginning with the first seminars of the 1950s. With numerous polymathic allusions, jokes, and non sequiturs, Lacan attempts a "return" and a self-conscious rewriting of Freud from the perspective of a rank outsider, pre-emptively exiled from the Freudian school for having been born too late, in the wrong country, and medically trained outside of the psychoanalytic tradition. By the same token, texts such as Memoirs of My Nervous Illness and Ulysses depict the psychic contortions of sidestepping Oedipal conflict through elaborate delusions and blunt disavowals of the father's potency. In sum, the trajectory of modernist intellectual life, especially psychoanalysis, turns on tendentious and broken relationships between teachers and students, as technical and artistic disciplines struggled to keep pace with cultural upheavals of the period.