In antiquity, public speaking was based on a set of linguistic strategies for obtaining agreement, with a good command of rhetoric seen as an asset. In the post-classical period, rhetoric was vilified and its status diminished due to the increasing (scientific) demand for tonal neutrality in discourse and the sublimation of oratory into printed material. In principle, Dante would have been respectful of the tradition governing epic speech-making, but ultimately chose to depict Ulysses’ fate in Inferno XXVI as a case of morally suspect rhetoric, exaggerating the hero-sinner’s deceptive skills and wanderlust as concepts antithetical to pietas, the idea of devotion espoused by Aeneas, Virgil’s hero. Tennyson’s depiction of Ulysses conforms in many ways to epic rhetorical conventions, though the post-Romantic incarnation of the Homeric hero does not precisely dovetail with the figure of classical and medieval tradition, instead fitting the Victorian mould of a restless wanderer, more concerned with intellectual pursuits than social pietas and oratorical trickery. By undertaking a comparative analysis of the rhetorical devices and presentation of pietas in these two works, a distilled appreciation of the fluctuating significance of Ulysses and notions of duty from the medieval era to modern times can be achieved.