Portrait of Sir Henry Guildford

This version of the portrait after Hans Holbein the Younger, focuses on the head and shoulders of the sitter, rather than depicting the three-quarters portrait in its entirety. The work captures the solemn expression of Guildford, at odds with his role as Master of Revels and carefully copies the detailed likeness of the sitter. However, the artist's own talent shines through in his deviations from Holbein' work. This can be seen in the added exquisite details of the under garment just showing under the fur cape and the fabric of his collar as well as the gold and black pattern on his robes. The artist omits the badge on Guildford's cap, focusing on the folds of the caps design and rendering the silver toggles in exquisite detail.

Guildford was a keen scholar and his humanist interests likely drew him to Holbein. The two almost certainly worked together in the planning of the revels at Greenwich in 1527 when a ‘Master Hans’ carried out a large portion of the decorative painting for the event. Guildford was one of the first in England to commission a portrait from Holbein and both the preparatory drawing and finished painting survive. Holbein reportedly also painted a portrait of Guildford’s wife Margaret, though this has now been lost, and painted Guildford himself again during his second trip to England in 1633. 

Sir Henry Guildford

Sir Henry Guildford (1489 - 1532) was an English courtier during the reign of King Henry VIII, Master of the horse, Comptroller of the Royal Household and various other offices. Son of Sir Richard Guildford and his second wife Joan, sister of Sir Nicholas Vaux, 1st Baron Vaux of Harrowden, Henry had been a childhood companion and cupbearer of King Henry VIII when he was Duke of York. As a result, Guilford remained one of King Henry’s closest friends and was appointed Esquire of the Body (personal attendant to the King) and Master of Revels when King Henry took the crown, meaning he was responsible for organising lavish entertainments at court. On one occasion, as part of this role, he and his half-brother Sir Edward, along with several others, impersonated Robin Hood and his men to entertain Queen Catherine of Aragon, whilst on another, to celebrate Twelfth Night, he organised a mountain to be presented to the King from which, when opened, Morris-dancers burst forth. 

Guildford’s antics were put to an end in the 1519 efforts of older statesmen to limit the influence of younger, hot-headed men on the King. He did, however, return to court soon after where he was appointed Comptroller of the Royal Household, developing a distinguished career.   

He married Margaret, daughter of fellow courtier Sir Thomas Bryan, in May 1512 with the King granting the manors of Hampton-in-Adren (Warwickshire) and Byker, Swineshead (Lincolnshire) to the couple. Though there is no record of Margaret’s death, Guildford married a second time to Mary, daughter of Robert Wotton of Boughton Malherbe, Kent. 

Guildford was a strong supporter of Catherine of Aragon and was strongly opposed to the King casting her out without the Pope’s blessing in favour of Anne Boleyn. He was so open with his views that Anne, recognising him as an enemy, threatened that when she became Queen she would have him removed from the office of Comptroller. He reportedly responded that she need not trouble herself, he would give up the role himself and immediately went to the King to tender his resignation. The King told him to pay no heed to what women said and insisted he take back the office. For a short time Guildford retired from court, though he remained one of the King’s council, though he passed away soon after in 1532. It is a mark of his friendship with King Henry that he was not only able to remain in his post until his death, but that the King was willing to overlook the opinion of the woman he was determined to split from the Catholic Church for in Guildford’s favour.