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My paper means to discuss the development and the application of Nabokov’s theories of translation in Anja v strane čudes (1922) and Eugene Onegin (1964). By using both Steiner’s and Newmark’s approaches, I will point out that Nabokov aims for a communicative translation, for a “hypotranslation”, in Carroll’s work, in order to make it more understandable to the Russian readership. Conversely, Nabokov uses a literal translation in Eugene Onegin, thus making the target text “awkward”. Such technique arises a sense of “foreignness” in the Russian readers, and paves the way for a metaphorical “hypertranslating” process. I will, therefore, demonstrate that the latter represents a generator of “overtranslating” elements, from a cultivated reader’s perspective, as a consequence of the clash between the Russian and the Anglo-Saxon worlds. Keyword Nabokov hypotranslation hypertranslation foreignness