This study assesses the implications of Ludwig Wittgenstein's philosophy for autobiographical writing, putting him in conversation with texts (fiction and nonfiction) that actively resist the act of writing about one's life. Chapter One traces the development of Wittgenstein's philosophy, from the Tractatus Logico-Philosophicus' limits of rational language (and the mystical silence beyond) to the ground-level 'album' of ordinary language games in Philosophical Investigations. Can Wittgenstein's professed inability to bring order to the latter - arguably an inevitable consequence of language games' endless proliferation - also be applied to writing about life, especially given the conspicuous autobiographical silence of Wittgenstein, whose planned autobiography never materialized? Chapter Two outlines how in Samuel Beckett's Molloy, traditional narratives of journey and procreation find their undoing through what Beckett calls 'efficient misuse' of language - a strategy that mimics his own oeuvre's autographical mode. The third chapter takes up Mesa Selimovic's Death and the Dervish, where a first-person account meant to untangle devolves into an amorphous narrative in which tangles, hallucinations, and fragments all become part of the search for a 'human' language. Whereas the two novels enact an inexorable unraveling, the two nonfiction works examined in the last chapter, Bernadette Mayer's Memory and Irena Vrkljan's Marina; or, About Biography, foreground the issue of language and memory, offering alternatives to the limitations imposed by habit and inherited hierarchical traditions. Mayer explores what Wittgenstein might call memory experiences, exposing the many ways that memory works as a language event, while Vrkljan uses memory as a space to bring together lives in a collective 'biography of words,' where Wittgenstein's aspect-seeing serves a crucial function. Finally, this dissertation argues for an acknowledgement - much like Wittgenstein's in the prefaces to his two major works - of certain language problems as essential aspects of the autobiographical task. At the same time, there should be a Wittgensteinian striving towards some impossible whole, complete understanding. Only then can the work function honestly and therapeutically, that is, to clarify and liberate.