In the Middle Ages the jester or fool was a familiar figure in courts across Europe. By the end of the sixteenth century they could be professional entertainers of the kind familiar to us from Shakespearian plays or so-called ‘natural fools’, people with physical or learning disabilities. The sitter here, Tom Derry (sometimes called Durie), belonged to the latter category and was employed by Queen Anne of Denmark, wife of King James VI and I. As servants in close proximity to their royal masters, the jester could enjoy considerable privileges. Tom Derry was apparently a much-loved member of the royal household with his own servants. When the royal court moved south after the Union of the Crowns in 1603, he followed his queen to London. However, it is unusual to find a jester as the subject for such a sympathetic portrait and the fact that the queen later commissioned another portrait of him by Paul van Somer suggests that Durie enjoyed exceptional favour.

The artist, Marcus Gheeraerts the Younger, was one of the most innovative and successful painters of the period. Born in Bruges, he came to London in 1568 with his father, also a painter, to escape the persecution of Protestants in Flanders. His earliest known paintings date from around 1592 and include the largest surviving portrait of Elizabeth I, the so-called Ditchley Portrait (National Portrait Gallery, London), which shows the queen in an elaborate jewelled white dress, standing on a curved globe of the earth. Perhaps his best-known work is the striking bare-legged portrait of the warrior Captain Thomas Lee, 1594 (Tate). By 1611 Gheeraerts had become a favourite among the various artists employed by Anne of Denmark; he made several portraits of  her as well as members of her famously extravagant court and in 1617 was referred to as ‘her Majesties painter’.

This portrait is inscribed with the date 1614. Derry wears a red doublet embroi­dered in gold and silver and proffers a large silver hospitality cup filled with wine. We can just glimpse the apron that he wears to protect his clothing from spillages. A heavy gold chain and an expensive ring hint at gifts from the queen and add to the ostentatious effect. The painter has caught something vulnerable yet dignified in the soft eyes and wrinkled skin of his sitter. There is no sign of condescension or any obvious clue to Derry’s role as a jester. It has been suggested that the very seriousness of the image might carry some underlying comic intent. However, while it is true that a jester’s position at court invited mockery and derision as much as curiosity, the so-called ‘fool’ could be admired and elevated for his natural sim­plicity and innocence. Here, it is the sheer humanity of the portrayal that captures our attention, and there is no hint of scorn in what seems to be an affectionate and compassionate image.

This text was originally published in 100 Masterpieces: National Galleries of Scotland, Edinburgh, 2015.