This dissertation places Wittgenstein and Nietzsche alongside one another in an attempt to deal with the question: "what is the role of the philosophy?" On the one hand Wittgenstein promotes a descriptive approach to philosophy, which insists that the philosopher should not meddle with practices but rather seek clarity and understanding as ends in themselves. On the other hand Nietzsche promotes a destructive and creative approach to philosophy, where the philosopher both dismantles values and offers a revaluation of values in their place. This work begins with a survey of remarks by the two philosophers and prominent interpretations of them on how best to conceive of and understand the philosopher and philosophy. In addition, the recent view of Nietzsche as a naturalist is responded to at length. If Nietzsche turns out to be offering substantive, naturalistic positions on human morality, the origins of religion, and so on, then he cannot be advocating a creative, spontaneous orientation towards perspectives. This work argues that while Nietzsche offers naturalized accounts of human practices, he does not mean these to be considered scientific hypothesis. After responding to this position, Nietzsche and Wittgenstein are looked at together, and what emerges is a shared goal: the creating and/or revealing of missed possibilities of human life. These existential possibilities are on the one hand always right in front of us, and yet they are seemingly out of reach and all too often passed over. Wittgenstein and Nietzsche, in their various ways, (re)open these possibilities. Finally, given this "hermeneutics of possibility," the final chapter argues that the way Wittgenstein and Nietzsche differ with respect to Christianity and religion is not primarily about their style of philosophy nor even about Wittgenstein's descriptive approach, but about the existential possibility that each has in mind to promote.