This painting, mentioned in Del Monte''''s inventory, shows a single lutanist singing a love song; and a related ''''''''carafe with flowers'''''''' is also listed in the catalogue of the Del Monte sale. From the seventeenth century there have been uncertainties about the gender of the singer. Baglione and the Del Monte inventory call him a boy; Bellori, who knew only a copy, calls him a girl. There are reasons for this confusion. One is the Renaissance fascination with androgyny---the singer is not much older than Shakespeare''''s Rosalind, who renamed herself Ganymede, and Viola, who renamed herself Cesario - and another is the Italian fashion for castrati. The lutanist, with parted lips, sings of love from the madrigal Voi sapete ch [''''''''io v''''''''amo] (you know that [I love you]) by the Flemish composer Arcadelt. In front of him is a violin and bow which invite the spectator to take part in a duet with him; the fruit and the vegetables, and indeed the music itself, imply the harmony that should exist between lovers.
Among the early works this painting must count as a virtuoso performance. The glass carafe and its flowers are painted with assured mastery, and Caravaggio is also aware of the problems of perspective that lutes and violins could cause; and he spotlights the solo player and his instruments so as to make them the main focus of attention, the carafe of flowers so that they are a secondary focus. One of his most talented followers, Orazio Gentileschi, was to paint a girl lutanist with a more beguiling sense of poetry, but without the sense of immediacy that was the hallmark of his master''''s craft.