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Abstract: The aim of the article is to study the three most striking cases of the Oswald Spengler’s influence on the USA authors (F. Scott Fitzgerald, J. Kerouac, A. Bloom). The subject of research is Spenglerian cultural concepts which appeared most relevant for the Americans and the ideological premises of the transfer of cultural concepts. The methodology applied in the article is one of the modern modifications of the comparative method – the study of cultural transfer (cultural movements of ideas and concepts and their consequent incorporation into the new culture). The beginning of Spengler’s influence on Fitzgerald dates back to The Great Gatsby. The attention is drawn to the fact that the title characters of the last two unfinished novels of the writer can be viewed as Faustian men at the beginning and end of the historical cycle respectively. Jack Kerouac belonged to the generation of “beatniks”. The very word “beat” goes back to the English translation of “cosmic rhythm,” the concept critically important for the worldview of Spengler. Kerouac developed the themes foregrounded by the German philosopher: the stupefying and destructive influence of the city on modern man, the phenomenon of alienation, the opposition of the intellect to real existence, the incomprehensibility of the concept of time, the meaning of memory, the insatiable desire of the Faustian man to move forward and to better oneself. Kerouac’s reinterpretation of the concept of “fellaheen” is analyzed; an assumption is made about the influence of Spengler’s ideas on the poetics of “spontaneous prose”. The general tendency of the American sociologist and philosopher Alan Bloom, whose famous book The Closing of the American Mind (1987) became the first sign of “cultural wars” in the USA, also fits into the Spengler paradigm. Bloom’s role in the intellectual life of the United States at the late 20th century is found very similar to what Spengler was for Germany of his time. Each of the three figures in question became exponents of generational cultural transformations (“the lost generation”, “beat-generation”, and the generation of “cultural wars”), which confirms the recurrent consonance of Spengler’s ideas to periods of paradigmatic cultural shifts. Conclusions made can be implemented for study and research of the 20th century USA culture and its relationship with European intellectual tradition.