This essay analyzes the theatrical drama Auto da Barca do Inferno by Portuguese playwright and musician Gil Vicente (1465-1536?) in light of the acoustic-literary theme of the song “O Pastor”, written by the also Portuguese music band Madredeus (1985-). With emphasis on the analysis of pastoral figure, the double allegory of the drama’s plot, the ambiguity of song’s tonalities, and the tireless recurrence to a third poetic imaginary presented to the reader-listener in the shape of a boat, it will try to show how the song questions the rigid parapet established by the dogmatic and imperialist Manichaeism of the Vincentian drama.