Russian prose writer and playwright whose works address the conflict between old and new mentalities in the early years of the Soviet Union.

Olesha was born into the family of a minor official. He lived in Odessa from childhood, eventually studying for two years at Novorossyisk University there. In 1922 he moved to Moscow, worked for the railway workers' newspaper Gudok (“The Whistle”), and wrote poetry and satirical prose sketches.

Olesha gained renown first as a poet. His fame as a prose writer came after the publication of his novel Zavist (serialized 1927, published in book form 1928; Envy), the central theme of which is the fate of the intelligentsia in Russia's postrevolutionary society. Olesha's obvious enthusiasm for the new state of affairs did not hinder him from seeing and conveying to the reader the dramatic clash between the rational industrial state and the creative aspirations of Nikolay Kavalerov, one of the main characters in the novel. This clash is also echoed in Kavalerov himself: he has talent and creative potential, but he throws it away. Envy is one of a number of 20th-century Russian novels in which the protagonists clash with Soviet reality and as a result find themselves marginalized.

Olesha's second widely popular book, Tri tolstyaka (1928; The Three Fat Men), was written for both children and adults. It is a story set in an unknown land about an uprising led by the gunsmith Prospero. (The name is an allusion to the magician of William Shakespeare's The Tempest.) The novel has the didactic and schematic qualities of a fairy tale and is filled with unexpected metaphors and dexterously shifting points of view. In The Three Fat Men Olesha displays the same mastery of style present in Envy and his short stories.

By the late 1920s and early 1930s, Olesha had published a series of short stories and plays, among which the play Spisok blagodeyaniy (1931; “A List of Benefits”) was staged by the director Vsevolod Meyerhold (Meyerhold, Vsevolod Yemilyevich). Olesha's openly lyrical speech in 1934 at the First All-Union Congress of the Writers' Union of the U.S.S.R. further bolstered his fame. After this, however, he published very little, although he often wrote for the cinema. For many years he worked on what was published posthumously as Ni dnya bez strochki (1965; No Day Without a Line); assembled from Olesha's notebooks after his death, it resembles a memoir, but its mix of sketches, essays, and other forms of writing defies categorization. It is often compared to Fyodor Dostoyevsky (Dostoyevsky, Fyodor)'s equally complex The Diary of a Writer.