The study is devoted to the study of the role of paradoxes in the novels written by I. Ilf and Eu. Petrov «The Little Golden Calf» and «The Twelve Chairs». In this aspect, the novels that have become world classics have not yet been the subject of detailed scientific study; an attempt to fill this gap determines the relevance of this article. The concepts of «antinomy», «dichotomy», and «intentionality» are considered. The study of the elements of paradoxes, their step-by-step tracing allows to reveal hidden meanings, the vertical context provides a better understanding of the linguistic personality of the characters and the author’s message. The paradoxical nature of evaluative characteristics can manifest itself not only in a horizontal context, but also in a vertical, diachronic one. The contexts containing the paradox extracted from the texts of the indicated novels were selected as the material of the study. The article concludes that in the language of literary works the paradox is used expressly, intentionally, it reflects the linguo-creative thinking of the authors, used as a stylistic device to create the image of a character, as an individualization of his speech, and also performs numerous other functions. It was revealed that the paradoxes used for the image of the main character, O. Bender, who is a strong linguistic personality, represent one set of qualities, and for Panikovsky - another. The paradoxical statements coming from Bender and the speech of other characters in the novels by I. Ilf and Eu. Petrov are psychological, they become persuasive arguments for situation awareness, a means of calming, creating the appearance of a lack of violence against the victim to cover up their own plans.