Tom Derry or Durie was the ‘fool’ employed by Queen Anne of Denmark, the wife of King James VI and I. Monarchs and some aristocrats maintained the medieval tradition of keeping a fool or jester as part of their household until well into the seventeenth century. Some jesters assumed the role as a profession, whereas others occupied the position because of a mental or physical impairment. A much-loved servant, the Queen commissioned portraits of Derry by two of her favourite artists. In this portrait by Gheeraerts, Derry is dressed in an expensive doublet embroidered with precious metals and with a heavy gold chain around his neck. He holds a hospitality cup, filled with red wine, which was shared by guests at ceremonial functions.