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While anyone proficient in English can read Fitzgerald’s texts as he wrote them, for millions of non-English speakers the only option is to rely on translations. The Great Gatsby alone has been translated into at least forty-two different languages. If we take into account that often more than one translation exists within each individual language community, we have to ask ourselves: are we all reading the same text? The novel under examination will be The Great Gatsby and its fifteen Italian translations to date. This article will first follow the editorial journey of the work in Italy, with focus on the first two translations. It will also discuss paratextual elements—the publishing companies, the series within which the novel appeared, dust jackets, product positioning, and so on—and will then concentrate on the transformation of the actual text. One of the debates within translation studies is how “faithful” the translator can or should remain to the original. This article will analyze the varying degrees of freedom available and the consequent effect on an audience which, for linguistic reasons, does not have access to the original version. Elements under investigation will include vocabulary, syntax, and stylistic devices—with specific attention to the way in which culture-specific references have been handled.