This little-known work of the great Florentine artist has only recently been re-identified (by me) as the portrait of a professional canterino. It is of great interest both for the status accorded to the sitter, a well-dressed individual in the preoccupied act of tuning his lira da braccio, as if about to perform, and for the Petrarch inscription etched into the back of the instrument which faces the viewer. It dates from the early 1480s, and so dates from a period when both civic and humanist practices of singing to the lyre were in full flood in Florence. The sitter could be a practitioner of either, or perhaps the distinction did not matter at the time. This short essay explores this ambiguity.