Will and the king became extremely close. He called the king “Harry,” “Hal,” or “Uncle,” the only person permitted to do so. The feeling of kinship was apparently returned because Will was included in at least three family portraits, and in the king’s personal psalter.
If Will ever married, there’s no record of it. I’ve seen claims that he had a son who was a court official under the rule of James I, but no documentation.
Like Richard III, whose skeleton was recently discovered, Will Somers likely suffered from juvenile onset scoliosis. He came to Henry’s court as a young man already afflicted with a “pronounced stoop” and his portrait in the king’s psalter shows one shoulder raised significantly higher than the other. Fortunately for him, it does not appear to have worsened, judging by his later portrait with the king and his children. That’s not certain evidence, of course, but he was still able to perform in his latter years.
Some scholars disagree with the portrayal of Will Somers as a witty “artificial” fool. Will is mentioned several times in John Heywood’s play Wit and Witless (1525-1530) in which Will is scathingly referred to as “sot Somer,” as an example of those on the witless side. However, the author seems to have resented Will for his closeness with the king, and it cannot be known if this was simply meant as an insulting “joke” at Will’s expense.
Secondly, there is a record from 1551 of a payment to a “keeper,” for Will, which would mean he was unable to take care of his own financial matters, but there are several instances where records seem to confuse Will and Patch, so it cannot be stated for certain.
On the converse, there is some contemporary evidence for Will’s wit. In a letter from Sir William Paget to the king in 1545, Paget references one of Will’s clever quips, and in 1553, one of Will’s quotes is used to illustrate a style of puns used in debate in the book Art of Rhetoric by Thomas Wilson.
Will seems to have acquired a reputation for kindness and generosity to the poor. Perhaps that is why his memory lived on in the popular imagination. He is a character in several 17th century books and plays. In 1676, a biography of him was written:
But this Will Summers was of an easie nature, and tractable disposition, who . . . gained not only grace and favour from his Majesty, but a general love of the Nobility; for he was no carry-tale, nor whisperer, nor flattering insinuater, to breed discord and dissension, but an honest plain down-right, that would speak home without halting, and tell the truth of purpose to shame the Devil; so that his plainness mixt with a kind of facetiousness, and tartness with pleasantness made him very acceptable into the companies of all men. —A Pleasant History of the Life and Death of Will Summers (Author was anonymous)
What though thou thinkst me clad in strange attire
Know I am suited to my own desire
And yet the characters described upon me
May show thee, that a King bestowed them on me
Around 1620, an engraving was made of Will, which can be seen to the right. The verse below it announces his clothing choice is his own preference, but was given to him by the king, whose initials are embroidered on the chest. Will's clothing is mentioned often in the plays and poems about him, often given as a reward for doing some task for the courtiers or king.
The clothing he wears in the engraving is very rich in style. The robe is from the latter period of Henry's reign and is either spotted fur, or embroidered velvet. His sleeves are elaborately slashed and runched, and he wears a gold collar around his neck; not a "collar of esses" which would denote a high office, but a thick, elaborate chain of three strands of gold links. His jaunty cap, likely made of velvet, has an ostrich feather that curls over the side. A jester's cap with bells is tucked into his belt. There is a suggestion of Will's hunched shoulder on the left side. Wearing the king's initials would have been a point of pride, signifying his allegiance, sort of like a team jersey today.
It is said that when Henry was in his final illness, Will heard that Richard Fermor had been jailed for taking clothes and some money to an imprisoned priest who had spoken out against the royal Supremacy. Will interceded on Fermor’s behalf and Henry granted him a pardon. After the king's death, some of Fermor’s attained property was restored.
Will remained at court through the short reign of Henry's son, Edward VI, and then the reign of "Bloody" Mary. He was said to be the only person at court who could make Mary Tudor laugh, and during her brief, sad reign, laughter may have been in short supply.
He seems to have retired after performing at Elizabeth’s coronation, and moved to Shoreditch, where—it’s believed—he died in 1560.