The Ancient Green philosopher Sextus Empiricus provides us, in the Outlines of Skepticism, with arguably the most complete surviving account of Pyrrhonian Skepticism. He conceived of Skepticism as a way to live your life peacefully, free from the worries that are caused by oppositions in the world around us. For every claim, there is an equally plausible opposition, and this creates stress for the dogmatist. The Skeptic, on the other hand, by recognizing that there are oppositions and thus practicing suspension of judgement along with investigation, is able to be tranquil in the face of oppositions. To better be able to understand Skepticism, it is useful to see a practical application. Therefore, I will argue that Rick Blaine, from 1942’s Casablanca, matures into a Skeptic during the course of the film. Although the film is a work of fiction, there is enough character development to argue that the earliest version of Rick chronologically is not a Skeptic. As the film progresses, we can see his development and at the end of the film he is able to face making the decision to send his love, Ilsa, away without experiencing turmoil. I will also argue that the film has Skeptical qualities of its own which mean that it should be read as more than a wartime propaganda piece. Both of these arguments will be shown by completing a close reading of the film’s script, written by Julius and Philip Epstein and Howard Koch, as documented in Casablanca: Script and Legend by Howard Koch as well as my viewings of the film. The reading has been organized into the four phases that Rick experiences in his relationship with Skepticism.