Describing the famous monstrous character Shuten Dōji from Japanese medieval legend, Irene H. Lin explains that demons in their historical context “became symbols of potentiality, albeit ambiguous, possessing both positive and negative possibilities, of both sacredness and pollution, and thus were effective mediators between the inside and the outside realms, in social, political, and religious spheres.” Following her argument, I analyze the character potential of Shuten Dōji as a semi-cannibal. Taking studies of cannibalism within the context of colonizer/colonized relations, I read the act of man-eating in the Tale of Shuten Dōji as a figurative act that possesses “positive possibilities” of mediating different realms not only by the character’s explicit metamorphosing power but also by his charismatic quality. Maggie Kilgour points out that, in contrast to cannibalism in the past that was used to construct differences between the colonizer and the colonized, cannibalism at the present time is used to transcend the boundaries of the binary oppositions such as the self and the other, the natural and the cultural, etc. The Shuten Dōji narrative questions us the distinction between humanity and monstrosity by presenting both the monstrous and the human characters as man-eating, while giving depth to the characterization of Shuten Dōji by describing him as a talkative and even heroic figure. Focusing on the ambiguous status of Shuten Dōji, who is in between monstrosity and humanity, I will seek out the source of creative and artistic power in the act of man-eating of the legendary figure.