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Born in Shropshire, Sommers came to the attention of Richard Fermor, a merchant of the Staple at Calais, who brought him to Greenwich in 1525 to present to the King. Impressed by Sommers' sense of humour, Henry promptly offered him a place at court. He was soon in high favour with the King, whose liberality to him is attested by the accounts of the royal household.
Sommers remained in the King's service for the rest of Henry's life; in the King's later years, when he was troubled by a painful leg condition, it was said that only Sommers could lift his spirits.
The jester was also a man of integrity and discretion; Thomas Cromwell appreciated that he sometimes drew the King's attention to extravagance and waste within the royal household by means of a joke.
Court jesters were permitted familiarities without regard for deference, and Sommers possessed a shrewd wit, which he exercised even on Cardinal Wolsey. However, he did occasionally overstep the mark. In 1535, the King threatened to kill Sommers with his own hand, after Sir Nicholas Carew dared him to call Queen Anne "a ribald" and the Princess Elizabeth "a bastard".
Robert Armin (writer of Foole upon Foole, 1600) tells how Sommers humiliated Thomas, the King's juggler. He interrupted one of Thomas' performances carrying milk and a breadroll. Will asked the King for a spoon, the King replied he had none and Thomas told him to use his hands. Will then sang:
'This bit Harry I give to thee
and this next bit must serve for me,
Both which I'll eat apace.
This bit Madam unto you,
And this bit I my self eate now,
And the rest upon thy face.' 
He then threw the milk in his face, ran out, and Thomas was never at court again. Sommers also used his influence to compensate an uncle who had been ruined by an enclosure of common land, though it took a very subtle appeal by Sommers to Henry.
In Thomas Wilson's Arte of Rhetorique (1553–60), Will is quoted telling the financially hard-up King: "You have so many Frauditors [Auditors], so many Conveighers [Surveyers], and so many Deceivers [Receivers] that they get all to themselves."
Sommers is believed to be portrayed in a painting of Henry VIII and family at the Palace of Whitehall, completed around 1544-5 by an unknown artist. He also appears with Henry VIII in the Psalter of Henry VIII which was made for the King and is now in the British Library (MS Royal 2. A. XVI. A previously unknown picture in which he appears was discovered in 2008 at Boughton House, Northamptonshire.
After Henry's death, Sommers remained at court, eventually retiring in the reign of Elizabeth I.
Under Mary I, Will's role was mainly ceremonial, and as a sidekick to Mary's personal fool, Jane Foole. Will was reputed to be the only man who made Mary laugh, apart from John Heywood. Will's last public event was the coronation of Elizabeth I.
He was probably the William Sommers whose death is recorded in the parish of St Leonards, Shoreditch, on 15 June 1560. A modern plaque in the church commemmorates his burial there.
William Sommers made a number of appearances in 16th and 17th century drama and literature: for example, Thomas Nashe's Pleesant Comedie called Summers last Will and Testament (play first performed in 1592, published in 1600), Samuel Rowlands' Good Newes and Bad Newes (1622), and a popular account, A Pleasant Historie of the Life and Death of William Sommers (reprinted 1794). See also John Doran's History of Court Fools (1858).
In Margaret George's 1986 fictional "The Autobiography of Henry VIII," Will Somers protects the manuscript from Queen Mary, who would destroy it. "Somers" adds observations in his own hand that throw light on the old king's hypocrisies and failings.
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