He was said to have been born in Shropshire, and 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.
Thomas Cromwell appreciated that Sommers sometimes drew the King's attention to extravagance and waste within the royal household by means of a joke.
[3] Such individuals were permitted familiarities without regard for deference, and Sommers possessed a shrewd wit, which he exercised even on Cardinal Wolsey.
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".
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 [Surveyors], and so many Deceivers [Receivers] that they get all to themselves.
The image of Will Somers in Henry VIII's Psalter, British Library, Royal MS 2A XVI, shows him wearing a short green coat with a hood.
William Sommers made a number of appearances in sixteenth- and seventeenth-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).
In Margaret George's 1986 fictional The Autobiography of Henry VIII, Will Somers protects the manuscript from Queen Mary, who would destroy it.
Sommers is shown as Hannah's very sympathetic mentor, training her in the art of being a jester and unstintingly sharing his professional secrets with her.
The real Sommers was younger than Henry VIII but in this series he is portrayed as an elderly and sardonic attendant who provides the grieving king with consolation following the death of Jane Seymour.
In April 2016, Ottawa actor and playwright Pierre Brault premiered his solo show entitled Will Somers: Keeping Your Head, speculating on Sommer's life and the role of comedy has in speaking to power.