This article analyzes an adaptation of Canto 33 of the Inferno, a musical setting of Count Ugolino composed by Gaetano Donizetti (1828). The composition is first presented within the frame of its contemporaneous aesthetic, one that treats Ugolino as a pathos-inspired tale of human suffering. Donizetti’s composition, however, fails to align itself to this tragic reading due to structural contradictions that prevent the listener from sympathizing with the musical agent. To address this divergence, the article extends the most recent theories of musical narrative by Byron Almén and Michael Klein to propose an ironic reading of the work, essentially a subversion of the structural and ideological expectations of a nineteenth-century setting of the character. This strategy opens up an interpretative space for a richer understanding of the composition by placing extant Dantean criticism and musical analysis in dialogue—thereby, considering Ugolino through the lens of his insincerity and paternal failings.