This thesis uses the philosophy of Friedrich Nietzsche to explore and explain moral and literary problems in Vladimir Nabokov's works. Although a phalanx of 'Nabokov and X' studies exist, there remains no English-speaking work that focuses solely on the relationship between these two figures. This seems strange given their deep connection to the Russian Silver Age, Nabokov's frequent references and allusions to Nietzsche, and their thematic similarities. The many knotted issues in Nabokov studies - Lolita's relationship to morality, Pale Fire's internal authorship, Nabokov's relationship with his readership - often create impasses that frustrate interpretation. By breaking with traditional approaches in Nabokov studies; by 'answering back' to Nabokov rather than adhering to the conditions he suggested for reading his work, I demonstrate how a Nietzschean analysis can negotiate such interpretative stalemate and act as a fulcrum to problems in Nabokov's fiction. The study is divided into three sections, each with two chapters: 'Nietzschean Engagements', 'Nietzschean Readings' and 'Beyond Nietzsche'. The first section deals with Nabokov's more obvious points of contact with Nietzsche through allusions and references. 'Nietzschean Readings' looks at Nabokov's texts through the lens of Nietzschean philosophy, allowing us to frame certain literary problems differently. The last section describes how Nabokov moves away from Nietzsche - from respectful pupil to rebellious disciple. Each chapter of the thesis looks at existing problems in Nabokov's oeuvre and challenges the assumptions surrounding them. For the most part, this challenging is uncomfortable insofar as it asks readers to question, perhaps even doubt, the very mechanisms that they go about understanding literature. One of the main concerns running through the thesis is the insistence that such disconcertment is not only rewarding in respect to understanding Nabokov's works but also beneficial to the reader's capabilities.