The sitter in this portrait was first identified as Sir Robert Sidney by F.M. Kelly in an article in The Connoisseur in 1937 (op.cit.). Kelly, who had seen the picture when it was in the Cowper collection and hung in the dining room at Panshanger, recognised what he understood to be the same portrait in a description of a portrait which he had come across in an inventory at Leicester House, made shortly after the death of Robert Dudley, Earl of Leicester, dated 20 September 1588, which reads 'A picture of Sir R. Sidney leaning on his holberde and his armore lying beside him'.
Sir Robert Sidney (1563-1626), the second son of Sir Henry Sidney, and the nephew of Robert Dudley, Earl of Leicester, who in historical terms has been eclipsed by his elder brother Sir Philip Sidney (1554-1586), was himself a distinguished soldier, statesman and patron of literature and fought with notable success against Spain in the Low Countries from 1585. He was also heir to his uncles Robert Dudley, Earl of Leiceister (d. 1588) and the Earl of Warwick, and was created Earl of Leicester in 1618.
However, Kelly's identification is not certain, for as Sir Roy Strong has pointed out an earlier inventory of Leicester House, of 1584, includes what from the description would appear to be the same picture described as 'one of Sir Thomas Knollis leaning on a holbert with his armour lying by him' (R. Strong, op.cit., p. 299, note 9).
Moreover, on stylistic grounds, it has been suggested that the portrait may be dateable to the 1590s, or even later, rather than the 1580s, which would mean that it may not be the picture recorded in the Leicester collection at all. It can be compared to other portraits such as Marcus Gheerhaerdts' Captain Thomas Lee, dated 1594 (Tate Gallery, Dynasties, catalogue to the exhibition at the Tate Gallery, ed. Karen Hearn, 1995, no. 120). Sir Roy Strong, in the introduction to his essay The Elizabethan Malady in the collection of his essays The Tudor and Stuart Monarchy, published in 1995, commented of this portrait that 'I have no doubt that it goes back to a lost Elizabethan painting but it is certainly a later copy on canvas'. However, he has since had the opportunity to reexamine the picture and is now convinced that it is a work of the late 16th Century.
The sitter in the portrait affects the melancholic attitude which became fashionable in the late sixteenth century and Sir Roy Strong comments:
'He appears here as a sad-faced, curly haired young man of twenty or so, attired in black, standing in solitude and musing amidst a forest glade, with a little brook nearby and a besieged city in the distance. He not only has the despondent pose of the innamorato of Burton's title page and Rowlands's Melancholy knight, but also the alfresco setting beloved of melancholics.'
Although we do not know who painted the present portrait, its affectation of melancholy - one of the earliest known portraits of this type - links it iconographically to other late 16th and early 17th Century portraits, such as Isaac Oliver's celebrated portrait miniature of Edward Herbert, 1st Baron Herbert of Cherbury, of circa 1613 (private collection), and Nicholas Hilliard's portrait of a young man believed to be Henry Percy, 9th Earl of Northumberland of circa 1590-5.
The background of the picture shows a, as yet unidentified, besieged city, which may allude to a continental campaign in which the sitter took part. The mountains apparent beyond the city, however, appear to exclude the Low Countries where Sir Robert Sydney and his brother served.