Born in Amsterdam, Willem Drost was, according to Houbraken (De groote schouburgh, 1718-1721, III, p. 61), a pupil of Rembrandt possibly in or shortly before 1650. His earliest dated paintings are two pendants of 1653: a Portrait of a man (New York, Metropolitan Museum of Art) and a Portrait of a woman (The Hague, Bredius Museum). In 1655, he travelled to Italy, working in Venice and, possibly, briefly also in Rome; there, he may well have encountered another of Rembrandt's pupils, the Danish-born Bernard Keil, known as Monsù Bernardo, as well as Johann Carl Loth, with whom Houbraken relates that he worked, and both seem to have been influential on the Dutch artist. Drost's Italian paintings display a softness of handling, and sensitivity to light - aptly described by Bikker as 'a tenebrist style, derived from Jusepe de Ribera's example' (op. cit., p. 1) - that marks them as quite distinct from those of his smoother, more distinctly Rembrandtesque Amsterdam period.
The present work is from that Italian period. Sumowski, loc. cit., compared it to the signed Boy with a Dove in the Tiroler Landesmuseum Ferdinandeum, Innsbruck (inv. no. 602), with which it shares the same model, wearing the same straw hat. As noted by Bikker, loc. cit., the treatment of dappled sunlight on both faces is also closely comparable, as are the parallel hatchings of the brushwork in the face, and the fluid treatment of drapery: the latter feature and the all'antica design of the gown recurring also in the Portrait of the artist as Saint John the Evangelist sold in these Rooms, 9 July 2003, lot 34. Bikker suggests that the 'warm colouring, light background and looser technique' argue for a later dating in the Venetian period than the Innsbruck painting. The motif of a boy with a flute recurs in three others of Drost's Italian-period paintings: as Mercury in the Mercury and Argos in the Gemäldegalerie, Dresden (inv. no. 1608); the Flute Player, sold in these Rooms, 27 October 2004, lot 23; and the Young Boy holding a flute in the Uffizi, Florence (inv. no. 2935, 1890 inventory).
Although much sought after by contemporary collectors in Amsterdam and Venice, Drost's tragically early death in Venice in 1659 for long prevented his recognition by later generations. His pictures were sold under a bewildering variety of attributions, ranging from the inevitable Rembrandt to Giorgione, Tintoretto, Van den Eeckhout, Loth and Murillo; his own identity became confused, being known variously as R.R. Drost, P. Drost, Cornelis Drost, Gerard Drost, Wilhelm Drost, Drost van Terlee, Jacob van Drost and even Van Dorst (ibid., p. 3), and Hofstede de Groot, in his Thieme-Becker entries, listed two Drosts: Willem in Amsterdam and P. Drost in Italy. It was Wilhelm Valentiner who first reunited the artist's oeuvre under his correct name ('Willem Drost, pupil of Rembrandt', Art Quarterly, 2, 1939, pp. 294-325), but it was not until the last thirty years - indeed possibly only with Bikker's 2005 monograph - that the artist's Italian period begun to receive the appreciation that it so evidently deserves.
In a private communication to the owner dated November 1990, Professor Werner Sumowski described the present painting as 'ein wirklich bedeutenders Objekt ersten Ranges' ('a truly important work of the first rank'); Professor Somowski dated the painting to shortly after 1655, early in the artist's Italian period (1994, loc. cit.).