We analyze the process of appearance and approval of orphanhood motive in V. Astafyev’s work. We substantiate its connection with autobiographical episodes from the prosaist’s life. The purpose of work: to prove the idea of origin and institutionalization in V. Astafyev’s prose of a character’s special type through emphasizing the motive of orphanhood. The relevance of the study is due to the inexhaustible interest in the prosaist’s unique work on the part of criticism, literary studies, reading community. Based on the stories material of the turn of 1950–1960s (“Pass”, “Starodub”, “Starfall”, “Theft”, “Last Tribute”) we establish the typological similarity of Astafyev’s characters both among themselves and with the characters of Russian literature classics (N.M. Karamzin, A.I. Kuprin, M.M. Prishvin). We argue the idea of fundamental commonality of Astafyev’s character-orphan with the type of “natural”, “untutored” person. We express and prove the assumption that this community, among other things, is the result of V. Astafyev’s reflections on the social and ethical problems that concern him: the spiritual and moral loneliness of a modern person, the loss of ethical and social ties between generations, a consumer attitude to nature, a separation from origins. We find a deep connection between the actualization of the orphanhood topic in the prosaist’s work and the large-scale social cataclysms of the twentieth century (military conflicts, socio-political upheavals, urbanization, disintegration of the traditional village, corrosion of once stable family values).