The purpose of this essay is to investigate the similarities between the main character in John Kennedy Toole's novel A Confederacy of Dunces, Ignatius J. Reilly and the main charcter in Miguel Cervantes' novel The History of Don Quixote de la Mancha. The emphasis lies on various traits and features of the respective protagonists, but the structure of the novels is included in the investigation.The heroes are similar; are presented in similar humorous incidents, moving from one environment to another; and they both are presented in novels containing similar structural elements. In combination, the similarities in main character and in structure, that of the picaresque novel, create similar heroes, even if the gap in time between them is more than half a millenium, and in space between Spain in Europe and the southern parts of the USA. Hopefully I have shed some light on what makes these two different characters