This essay examines the Folio version of Othello 4.3 via textual, performance and transnational analytic models in order to contextualize Desdemona’s Willow Song against the sung performances of English female ballad sellers and the Italian actress-singers of commedia and court fame. In this way, the essay argues that modes of female theatricality were contested at the heart of the dramatic and Shakespearean canon. The Folio Willow Song scene reworks the widely circulating trope of the lamenting abandoned woman, a figure whose virtuosic distress captivated audiences of the celebrated Italian commedia and court singers during the late sixteenth and early seventeenth centuries. One paradigmatic instance of virtuosic song and verbal dexterity, Isabella Andreini’s La Pazzia d’Isabella (1589), is examined to propose Othello 4.3 as a bravura demonstration of the boy player’s practice in opposition to women’s performance, staking a claim for the virtuosity of the English boy in competition with the foreign actress. Further, given the ongoing scholarly debates over the absence of the Willow Song from the 1622 Quarto and its status in relation to the stage, the essay suggests that the virtuosity required of the English boy actor in the song’s performance feeds into casting practice and hence can illuminate the scene’s textual history.