The article discusses two records of the journeys to the Soviet Union by the American writers E. E. Cummings and J. Dos Passos. In 1928, Dos Passos saw the country as a compelling example of success in building a new society, whereas Cummings denounced the 1931 USSR as the embodiment of Dante’s Hell. A number of reasons can account for that. Mutual interests that had brought Dos Passos and Cummings together mainly came from their belonging to the same generation and social circle. At the same time, their existential priorities could not have been more different: Dos Passos was preoccupied with pursuit of social justice, while Cummings remained apolitical. Another reason is that Cummings and Dos Passos were exposed to two different Soviet Unions: Dos Passos witnessed the USSR during its late NEP years, with artistic freedoms still mostly in place, whereas Cummings visited the country in the early days of the Great Purge. The subsequent historical events confirmed Cummings in his loathing of the USSR and prompted Dos Passos to lose faith in the country. The article offers extensive supplementary material consisting of correspondence, extracts from memoirs, and publications translated into Russian for the first time.