The article analyzes the image of America created by S.A. Esenin after his trip to the West with I. Duncan in the essay “Iron Mirgorod” (1923) and offers a comprehensive analysis of the poetics and the main sources of his text. Esenin was the first Soviet poet to visit America and create an essay about it, taking into account the rich literary tradition and his own vivid impressions. During his four month stay in America the poet lived in the New York City and visited 14 cities, in 11 states: Baltimore, Boston, Detroit, Indianapolis, Kansas City, St. Louis, Cleveland, Toledo, Toronto, Louisville, Memphis, Milwaukee, Philadelphia, Chicago. In connection with the history of the creation and publication of the essay, the article pays attention to the ambiguous semantics of its title, its connection with reality and literary sources — the cycle of essays by M. Gorky’s In America (1906) and N.V. Gogol’s works, including the collection of novellas Mirgorod (1835). The researcher analyzes the multilevel content, the correlation between the external and internal dialogue and the creation of a complex and contradictory image, in which the showy, festive, carrying the “banner of industrial culture” is contrasted with the “music hall” America. The article reveals Esenin’s polemics with the poem 150 000 000 writen by Mayakovsky “on the basis of pictures” taken from old magazines, “translating Whitman” (most of Esenin‘s attacks against Mayakovsky were not published) and his controversy with Russian urbanists (those from “Kuznitsa,” “LEF”). Esenin’s deep concern for the problems of modern spirituality and culture was expressed in categorical and sometimes shocking tone of his assessments and judgments, oddity of style and the pecularity of genre — the essay is written in an ironic manner balancing between satire and grotesque. Carrying on a dialogue with Gogol, Esenin extremely sharpens the contradictions of real America and warns against choosing the American path of development with its exceptionalism, false pride of being “cultured”, “immersion in business” and “the power of dollar.”