Through a comparative approach, the research aims to identify the ways in which the advertising artist Kirill Chudinskiy (the 2008 Volkswagen AG advertising campaign) interprets the imagery of René Magritte’s work “The Son of Man” and to discover the main means of representing the cultural meanings of the classical painting in the advertising product. The paper examines the features of Chudinskiy’s creative interpretation of the images of the classic painting masterpiece, as well as various means of artistic representation (allusion, symbol, allegory, depersonalization, antithesis, anthropomorphism), which help create the image of the advertising reality. The scientific novelty of the research is accounted for by the fact that the comparative approach to studying an advertising product (poster) allows for deciphering the content of the cultural dialogue between a contemporary artist and the legacy of the past; revealing the aesthetic value of a digital painting; and identifying affective techniques used in the process of creating a mass product and provoking the consumer to perceive the experience of classical art through the discovery of cultural text structures. In addition, the studied advertising product of 2008 by Volkswagen AG has not previously been the focus of researchers’ attention. As a result, it was found that, firstly, the interpretation of the image of the central character in Magritte’s work allows the advertising artist to create a hero of his time, expose his vices, while simultaneously engaging the viewer in an intertextual dialogue. Secondly, by offering his own compositional solutions in the poster, Chudinskiy, to some extent, provokes the viewer, ironically commenting on the subordination of modern people to the world of things, while simultaneously encouraging the viewer to acquire a thing, i.e., a product, through advertising. Thirdly, by transforming the images of the sky, the sea, and man, which are symbolic on the canvas of the Belgian surrealist, Chudinskiy, on the one hand, actualizes the reality of the advertising product, and on the other hand, inspires the recipients with the idea that they will become part of this reality the moment they acquire the product. Fourthly, the creator’s intellectual game with the recipient through the work of art encourages the consumer to decipher the cultural text, i.e., to engage in cognitive activity, relying on knowledge, associations, and memory.