This paper aims to make psychoanalytic theories resonate with artistic expressions of pathological jealousy. From this perspective, numerous novels, short stories, theatrical plays, and films from ancient and contemporary periods are called upon to put fundamental Freudian and Lacanian concepts to the test. First, the author explores object jealousy, conveyed through the bisexual feelings of the Oedipus complex, female rivalry, and universal feelings of unfaithfulness. The latter is revealed by the emblematic figure of the paranoiac who is able to penetrate the unconscious of the other. The article then turns to pre-Oedipal specular aggressiveness, as originally expressed in the fraternal intrusion complex and pervaded by the fascinating and alienating desire of the Other. Jealousy is thus considered to be a mixed pathos amalgamating suffering and pleasure, a controversial emotion that is prone to increase boundlessly and reach the mythical jouissance of the Other. Finally, the article opposes the jealousy metabolized by analytic transference and the rivalry intrinsically exacerbated in the psyche of the artist.