After a survey of the unusual publication history and the polarizing critical reception of A Confederacy of Dunces, it is shown that the novel’s picaresque surface hides an artfully designed structure that tells about the hilarious encounters of programmatically named characters who represent New Orleans’ ethnic diversity. This article investigates the character of Ignatius J. Reilly and the opposition between his medieval world view and that of his twentieth-century antagonists and its reflection in the subversive contrast between Ignatius’s reliance on Boethius and his rejection of Mark Twain. It shows how Ignatius’s rude behavior contradicts his pious beliefs and makes him a satirist satirized, discusses his fascination with the movies as intertextual play with Salinger’s The Catcher in the Rye and Percy’s The Movie-Goer, explains Toole’s strategies for creating both situational and verbal comedy, and shows that Ignatius’s linguistic flights of fancy go back to his creator’s academic work on Lyly’s Euphues (whereas the other characters’ ways of speaking represent New Orleans’ linguistic variety). This article outlines the unsavory, partly Swiftian traits of Ignatius’s repellent corporeality and reveals the easily overlooked reasons for his distasteful behavior. It reads the novel’s open ending as the doublepronged result of the medieval notion of the arbitrary workings of the rota Fortunae and the twentieth-century ethics of reward and punishment. It also points out the weaknesses of Toole’s overambitious novel and concludes that, despite these shortcomings, it is an accomplished example of narrative art.