This comparative study investigates the epic lineage that can be traced back from Derek Walcott’s Omeros and Ezra Pound’s Cantos through Dante’s Divina Commedia to the epic poems of Virgil and Homer, and identifies and discusses in detail a number of recurrent key topoi. A fresh definition of the concept of genre is worked out and presented, based on readings of Homer. The study reads Pound’s and Walcott’s poetics in the light of Roman Jakobson’s notions of metonymy and metaphor, placing their long poems at the respective opposite ends of these language poles. The notion of ‘epic ambition’ refers to the poetic prestige attached to the epic genre, whereas the (non-Bloomian) ‘anxiety’ occurs when the poet faces not only the risk that his project might fail, but especially the moral implications of that ambition and the fear that it might prove presumptuous. The drafts of Walcott’s Omeros are here examined for the first time, and attention is also devoted to Pound’s creative procedures as illustrated by the drafts of the Cantos. Although there has already been an intermittent critical focus on the ‘classical’ (and ‘Dantean’) antecedents of Walcott’s poetry, the present study is the first to bring together the whole range of epic intertextualities underlying Omeros, and the first to read this Caribbean masterpiece in the context of Pound’s achievement.