Abstract. The article deals with the fiction by Sergey Dovlatov, the famous Russian-American writer and journalist of the last third of the 20th century. The main aim of the article is to show the influence of the Russian folklore on the formation of the leading type of characters in Dovlatov’s prose. The paper shows that this type, which received in criticism the name of “Dovlatov’s outsiders”, is the realization of the archetype of the fool/the jester/the whacky, widespread in Russian and world folklore, a kind of variation of the fairy-tale “hopeless hero”. On examples of S. Dovlatov’s story “Pushkin Hills”, his collections of short stories “Ours” and “The Compromise”, the authors study not only the genesis of this type of characters but also their functions in the literary text, the impact on the content of works and readers’ perception. Much attention is attributed to the mechanisms of humor in Dovlatov’s texts. His characters are rebels and outlaws, whackies and jesters at the same time. They cannot “integrate” into the Soviet reality and destabilize it with their clownish behavior. The analysis of his prose shows that S. Dovlatov’s characters, and the humorous world in general, have an emphatically symbolic character. Therefore, the authors of the article, along with the traditional for the study of Dovlatov’s stories historical and genetic approach, involved mythological and structural-semiotic methods that contribute to the consideration of the symbolic nature of humor and its counter-sign function in the literary text. Keywords: Sergei Dovlatov, humor, Russian prose of the 20 th century, folklore, archetype, semiosphere, “outsiders”, good sense of humor, whacky, absurd.