One of the great mysteries of seventeenth-century Italian art is the identity of the Neapolitan painter known as The Master of the Annunciation to the Shepherds. Despite a century of proposals, there is no consensus as to the painter’s identity, yet little effort has gone into trying to understand the works themselves. This essay considers The Painter’s Studio (Colección Masaveu, Madrid), a witty and self-reflective meditation on the painter’s practice as a whole. The assemblage of painted objects in the painting provide a key for understanding aspects of the underpinnings of the painter’s otherwise unknowable artistic, intellectual, and religious ideals, as well as providing clues to the potential meaning of his celebrated paintings of shepherds.