Abstract Loneliness is a phenomenon observed in modern times with both individual and social dimensions, and in this context, it has become a concept frequently addressed in interdisciplinary studies. Although loneliness as a term evokes physical separation, it is essentially a multi-layered emotion that refers to situations in which an individual's desire for recognition and acceptance is not met. Loneliness is therefore defined as an existential feeling of not being noticed as well as social isolation. Approaching the subject through literature makes it possible to understand how this multifaceted concept takes shape in the inner world of the individual. In this study, the stories of Sait Faik Abasıyanık and Anton Chekhov, two important figures of Turkish and Russian literature, titled The Man Created by Loneliness and Misery (Тоска), respectively, were taken as the basis for our analysis within the framework of the theme of loneliness. The reader or researcher's recognition of the similarities or differences identified because of comparative studies is a valuable effort that paves the way for a correct, multi-faceted and layered interpretation of the text. In these two works, which were handled with the comparative analysis method, the internal conflicts of the characters and their relationships with their environment were examined, and the similarities and differences in their experiences of loneliness constituted the conclusion. Keywords: Misery, The Man Created by Loneliness, loneliness, comparative literature.