The highly sensitive and enigmatic bronze bust offered here is based on the left bronze statue of a cherub on the tomb of Pope Paul III in St Peter's, Rome, cast by Guglielmo Della Porta in 1549 (Avery, op. cit., fig. 230). However it is made more interesting by the fact that it bears a number of stylistic similarities with the works of the paterfamilias of Italian mannerist sculpture: Giambologna. In 1550 the young Giambologna visited Rome and spent the following two years closely studying the works of ancient and contemporary sculptors. There can be no doubt that the young Fleming studied della Porta's tomb for the Pope Paul III, and in particular the cherub, if one considers its closeness in style and composition with Giambologna's Fishing Boy in the Museo Nazionale del Bargello, Florence (ibid., fig 229), and the dolphin-carrying boys on the Neptune Fountain in Bologna (ibid., fig. 231), for example. The same can equally be said for the treatment of the hair and facial type on the head of the Zephyr from the Medici Mercury also in the Bargello (ibid., fig. 238), where one can see the author of this bronze modelling the hair in varying depths of relief and by having it radiating out from a central point at the back of the head and by piling the locks one upon the other above the forehead and on the sides. The comparisons are still further if one also considers the high and wide forehead, the almond-shaped eyes with heavily defined upper eye-lid, the small pointed nose, the narrow pert lips, the small pinched chin and shallow neck.
By virtue of its heavy cast and the rich warm brown patina it is highly likely that the present head dates from the second half of the 16th century, thus placing it firmly in the time that Giambologna was most active. However the very angular nature of the hair, which is handled as if being carved in wood, is unlike what one expects to see of the hairstyle on figures of Giambologna's mature works, which tend to be bold, organic and waxy. It is thus more likely that the present head was modelled and cast by a 16th century disciple of della Porta's familiar with Giambologna's style. However, one cannot entirely dismiss the possibility that the present head could also have been modelled by the young Giambologna in his years in Rome when he was evolving his skills from being a wood and alabaster carver and moving onto the more challenging media of bronze and marble.