This book expands and deepens linguistic theory as well as applies the resulting concepts empirically to narratives, in particular of Medieval literature. The first sections outline linguistic humor theory in general, and Raskin’s Semantic Script Theory (SSTH, 1985) as well as the General Theory of Verbal Humor (GTVH, Attardo and Raskin 1991) in particular. The following theoretical sections redefine the GTVH’s concept of logical mechanism—as most intricately connected to both the textual-narrative and the cognitive aspects of textual humor—in terms of set theory and expand the arsenal of the GTVH’s tools to make it applicable to humorous narratives. The focus here lies on the distinction between humor in the plot and humor of the plot of longer humorous narratives that are structurally similar to jokes. The reformulation of the concepts of shadow opposition and core opposition will then be the center of the application of the resulting expanded theory to selected narratives by Rabelais, Boccaccio, and Chaucer.