The work constitutes a type of masculinity in Russian literature of the second half of the 19th century and traces its development from pathetic, insect-like figures (Gogol's "The Coat", Cechov's "The Man in the Case", Andreev's "At the Window") to self-confident ones murderers (Dostoevsky's "The Gentle", Tolstoy's "Kreutzer Sonata", Tolstaya's "Whose Guilt", Andreev's "In the Fog"). Dostoevsky's "Untergrundmensch" ("Notes from the underground") occupies a central position, the variations of which are found in numerous texts of the time. The study shows the role played by the pathological loneliness of the characters on the narrative level, and the role played by gender relations and socio-historical hierarchies. Methodologically, it is based on the gender and masculinity studies of poststructuralism. The analysis of the texts shows the helplessness of a lonely, insecure male subject who rebels against a social order.