The research is dedicated to the well-known visit of the Irish dramatist Bernard Shaw and the British MP Lady Nancy Astor to the USSR in 1931. However, it seeks to avoid the format of a clichéd observation of commonly known facts concerning their stay in the Land of the Soviets and aims to concentrate on previously unknown circumstances of the preparation of that trip organised by representatives of the People’s Commissariat for Foreign Affairs and diplomats of the Soviet Embassy in London, on the one hand, and the media struggle evoked by that visit within the Soviet and the British press. The novelty of the research is provided by the use of numerous archival documents (AVP RF, RGALI) as well as quoting Bernard Shaw’s private correspondence and his friend Beatrice Webb’s diaries that have not been translated into Russian. The methodological foundation of this article is built upon the biographical and cultural-historic approaches; it also employs narrative techniques in recreating the historical background of Shaw’s visit, and content analysis in commenting on the media publications, and methods of archival research per se. Having considered the abovementioned documents, one can conclude that despite Shaw’s avid interest in Russia, his visit there was to a large extent spontaneous, which, together with Nancy Astor’s unpredictable escapades, caused considerable difficulties to the Soviet officials. Nevertheless, the variety of experiences offered to the British guests as well as the satisfaction of both reasonable and whimsical requests made by the dramatist managed to produce a favourable impression on the company and lead to Shaw’s companions giving generally positive feedback of the trip to the USSR whereas Shaw himself exalted in rave reviews. As a result, the victory scored by the Soviet soft power instigated a deluge of publications in the British media that aimed to discredit Shaw and Lady Astor as central figures of the trip. However, it cannot be said that those angry and even harsh commentaries caused any serious damage to their reputation or influenced their opinions of the USSR at the time.