Jan Stevan van Calcar (c. 1499-1545) was a Flemish painter and designer of woodcuts. Little is known of his early life but from 1537 he was in Venice where worked in Titian's workshop. He was known for his skill in portraiture, but is most recognised for his illustrations of the work of Andreas Vesalio, whom he met when the latter was studying at the university of Padua between 1537 and 1542. For Vesalio he executed three woodcut illustrations for the Tabulae anatomicae sex (1538) and worked on for the treatise De humani corpibus fabrica (1543). By 1545, he had moved to Naples where Giorgio Vasari, the artist and biographer, met him. Vasari noted, 'I came to know Johan of Calcar, a Flemish painter, who became very much my friend; a very rare craftsman, and so well practised in the Italian manner, that his works were not recognised as by the hand of a Fleming. But he died young in Naples, while great things were expected of him; and he drew for Vesalio his studies in anatomy'.

This miniature is one of the collection of copies of 224 self-portraits by artists in the Uffizi Palace, Florence, that Lord Cowper, the art collector and patron, commissioned Giuseppe Macpherson (1726-1780) to paint. He presented the miniatures to King George III in two batches, in 1773 and 1786. Macpherson followed the original self-portraits quite closely, but copied only the head and shoulders. He inscribed the artists' names on the backs of the miniatures – several differ from those in the modern Uffizi catalogue, notably: Bazzi, Bellini, Campi, Annibale Carracci, Gabbiani, Masaccio, Metsys, Moroni, Pencz, Licinio, Schiavone and Spada. None of the miniatures is signed, apart from Macpherson's own self-portrait, which is inscribed: Giuseppe Macpherson / Autore della serie (Giuseppe Macpherson / Author of the series).

Macpherson was born in Florence, the son of Donald Macpherson, a footman in the service of Alexander, 2nd Duke of Gordon. He was a pupil of Pompeo Batoni and painted miniatures and enamel portraits in Italy, France and Germany, finally settling in Florence. A James Macpherson is recorded in London and Paris in 1754 but it is not certain that this is the same person. He was described in 1776 as having a special talent for painting on enamel and as being 'almost the only painter in Europe who possesses this art to perfection'. He had a distinguished client list which included some of the crowned heads and dignitaries of Europe. In 1778, he was invited to add his own self-portrait to the famous painters in the grand duke's collection as it 'would do honour to Florence to enrich the collection with a work which shows that we still have some men of true merit' according to Giuseppe Pelli, director of the Uffizi at the time.