This dissertation is an attempt and, if you will, a temptation to engage with the ‘disturbing’ prospect of the truth of skepticism. All of Stanley Cavell’s works refer to the truth of skepticism, and yet the discourse surrounding this concept is sparse and often engaged minimally. The truth of skepticism is that “the human creature’s basis in the world as a whole, its relation to the world as such, is not that of knowing, anyway not what we think of as knowing” (The Claim of Reason, p.241). In order to make sense of what he means by what “we think of as knowing” Cavell provides a philosophical framework in which to understand skepticism and what it threatens: through his notion of “criteria” taken from Ludwig Wittgenstein; the concept of the “ordinary” derived from the works of J.L. Austin; and the “search for community” as a problem of “acknowledgement” or “avoidance” as opposed to a problem of knowledge. I argue that the “standard” (Stephen Mulhall’s) reading of Cavell fails to fully account for the truth of skepticism and I propose reading Cavell as a Nietzschean Versucher – one who attempts and searches endlessly, never fully embracing any particular view. By reading Cavell in this way, I explore how to do genuine philosophy and consider how to address the role of traditional epistemological problems in the face of Cavell’s framework. Beyond the traditional philosophical questions of skepticism, I address how the theoretical musings of the first half of the dissertation can be used in practice – or one could say how they reflect on the ordinary. Following Cavell, I connect philosophy and art as sister disciplines concerned with similar problems such as epistemological skepticism itself. To show these connections I analyze two plays and three films: Shakespeare’s The Winter’s Tale and Othello, alongside The Philadelphia Story (1940), Eternal Sunshine of the Spotless Mind (2004), and Her (2013). By engaging these pieces with Cavell’s philosophical framework in mind, I show how sexual jealousy is a form of living one’s skepticism in a real context that cannot be so easily dismissed by philosophers who claim that skepticism is somehow empty, confused, or nonsense. By showing how the threat of skepticism is a part of our ordinary lives, I conclude by considering how we might recover from our skepticism. Skepticism is not the end, it is the beginning.