This paper is the first step in my attempt to investigate the problem of phenomenology of the demonic in literature and in reality. Does the demonic exist apart from human experience? Does the perception of the demonic in the works of Russian literature exhibit any significant patterns which go beyond mere dependency on earlier works of literature? I would like to begin this line of investigation with the theme of demonism in Lermontov’s Demon in the light of the phenomenology of demonism by placing the poem in the context of its European predecessors. The large body of scholarship that exists on the phenomenology of the demonic outside of literature has been, unfortunately, often ignored by writers on the demonic in literature. I will try to incorporate the realm of the imaginary—the works of writers of the Romanticism—into the realm of the apparently real, and try to analyze the literary encounters with the demonic in comparison with mystical encounters with the demonic which real human beings seem occasionally to experience. What characterizes Lermontov’s Demon is a peculiar blend of human and satanic traits. The incompatibility of the human and the satanic in Demon raises an issue that is not limited to the Demon’s complex characterization and his uniqueness in the context of Romantic ideology, but presents a theological problem: the problem of Evil and the tragedy of Evil for Evil’s sake as perceived by Lermontov. By examining parallels between Lermontov’s Demon and its predecessors (especially Milton’s Satan and Byron’s Lucifer and Cain), I will underscore the complexity and ambiguity of the Demon’s tragedy. In order to demonstrate the importance of the unique approach taken by Lermontov this study will also establish and analyze: (i) the nature of the Demon as reflected in the antithetic co-existence of human and satanic in light of the phenomenology of the demonic as well as traditional Romantic demonism and (ii) the resolution of this contradiction in Lermontov’s approach. The analysis is based in part on the qualities of Romantic hero and considers such notions as love, temptation, alienation, and especially, the quest for possession.