As Charles Dempsey has argued, humanist culture often came about not through the revival of ancient models, but through the recasting of contemporary vernacular culture in light of ancient models. A central thesis of this book is that the ubiquitous humanist practice of solo singing to the lyre took shape principally in Florence, in the circles of Marsilio Ficino and Lorenzo de’ Medici/Angelo Poliziano, through adaptation of certain aspects of traditional canterino practice. This chapter sets forth what we know about the cantare ad lyram activity in these circles, establishes its clear relationship to civic practices, and argues for its integral role in both the Neoplatonic philosophy of Ficino and the vernacular poetics of Lorenzo and Poliziano. This leads to new perspectives on both Ficino’s “Orphic singing to the lyre” and Lorenzo’s lifelong involvement with singing to the lyre, both of which are typically regarded as idiosyncratic and tangential to their serious intellectual pursuits. This chapter also provides the occasion for considering the extraordinary figure of Baccio Ugolini, one of the great improvvisatori of his day, and a reassessment of Poliziano’s Fabula d’Orfeo in which Baccio sang the title role in 1480.