Ozymandias is one of Percy Bysshe Shelley’s most frequently anthologized texts in English school curricula. Owing to its lexical and syntactic clarity in addressing the theme of vanitas vanitatum, the sonnet would appear to pose no significant challenges for translators. Yet, this essay, by examining a range of translations that have shaped the Italian reception of Shelley, reveals how translation choices and strategies have resulted in markedly different texts. These variations often reflect the prevailing theories of translation and dominant poetic norms of a given period, or are deeply influenced by the translator’s individual poetics—who is, in some cases, a poet themselves. The essay focuses on a comparative analysis of four published versions of the sonnet (Carlo Faccioli 1902, Adolfo De Bosis 1928, Giuseppe Conte 1989, and Francesco Rognoni 2018), along with previously unpublished translations possibly attributable to canonical Italian authors such as Leopardi and Ungaretti. The essay concludes with reflections on literary translation in the age of artificial intelligence.