This dissertation attempts to create a conversation between the work of Willa Cather and Ralph Waldo Emerson. By examining the way their writings developed, biographical parallels, and shared themes, metaphors, and rhetorical strategies, I show how the works of these two authors, when read side by side, resonate with meanings neither possesses in isolation. The works of Cather and Emerson progressed through four stages. The first phase, evident in Cather\u27s early short stories and in Emerson\u27s youthful letters and journals, was an acute awareness of and anxiety about the limitations fate places on human power. I examine the second phase, an optimistic affirmation of the individual self, by comparing Cather\u27s O Pioneers!, Song of the Lark, and My Ántonia to Emerson\u27s early essays, particularly “Nature”, “The American Scholar”, and “The Poet”. Emerson and Cather next passed through a stage of crisis and skepticism focused around the loss of human relationships. In examining this stage, I hold up A Lost Lady to “Montaigne; or, the Skeptic” and The Professor\u27s House to “Experience” and conclude that Cather and Emerson each came to believe that human relationships are always susceptible to misunderstanding and loss because no person can really know another. In the final phase, exemplified by Cather\u27s Death Comes for The Archbishop and Emerson\u27s “Fate”, Cather and Emerson turned from skepticism to faith. Each did this by hearkening back to the fatalism of their youth. This fatalism forced Emerson and Cather to give up their former belief in the power of the individual in return for a greater sense of order and purpose in the universe. Finally, with Obscure Destinies, Cather took a retrospective look at her career. Each story in the volume corresponds to a phase of her writing life—“Neighbor Rosicky” with affirmative idealism, “Two Friends” with skepticism, and “Old Mrs. Harris” with fatalism. Cather\u27s final position was neither celebratory nor despairing but indicated an understanding and acceptance of the intractably complex and ambiguous nature of human life