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This paper examines the theme of mental illness in A. Chekhov’s The Black Monk (1893). The Black Monk is distinguished from other Russian literary works, which also have mentally ill characters, in its description of the protagonists’ psychiatric disorders through a medically accurate lens. Indeed, Chekhov possessed a keen interest in psychiatry as a doctor and this interest is directly reflected in The Black Monk. In this work, we find not only a detailed description of mental disorders but also the writer’s view of psychiatric illnesses, which is critical of the predominant ideas of 19th century psychiatry. Chekhov rejects traditional views of madness and introduces the reader to novel perspectives of mental illness by combining his medical expertise and his literary techniques. With these considerations, this paper aims to investigate how the writer’s medical-literary portrayals of mental illness enable the reader to understand both the origin of the protagonist’s disorder and his suffering. Furthermore, by examining the last scene, in which the protagonist meets death, it demonstrates how Chekhov provokes the idea of irreducible individuality and what it indicates in the aspect of otherness. Taken together, this paper argues that The Black Monk bears dual significance: its potential contribution to the field of Narrative Medicine and its philosophical implications for the notion of otherness.