In The Second Part of King Henry the Fourth, it is reported that Falstaff once boldly compared the King to a "singing man of Windsor" -- and was punished for doing so. Who is this "singing man."
Here we have another unsolved Shakespeare mystery. The throwaway reference to a "singing man of Windsor" must have tickled Globe audiences, but later playgoers (and scholars) can't guess why.
The singer owes his shadowy existence to Mistress Quickly, who inserts him into a one of her rambling narratives, the point of which is to claim that Falstaff has promised to marry her. "Didst thou not swear to me... when the Prince broke thy head for liking his father to a singing man of Windsor...."
Presumptuous indeed for Falstaff to compare his King to any ordinary mortal -- but what, we may ask, was so offensive about the "singing man" that his mere mention provoked the prince to violence? Misshapen, ugly, drunken, foolish? There must have been more jeer in the "singing man" than is now obvious.
The phrase "singing man" was a techical term that described not popular balladeers but professional choristers, usually priests, who were associated with a church or college. It's known that there was a priest of Windsor named Maudelen who resembled Richard II and was deployed as a figurehead in a plot to overthrow the king. Is it possible that Falstaff''s "singing man" referred to Maudelen and therefore challenged the legitimacy of Henry's kingship. Shakespeare knew this story (it appears in Holinshed's Chronicles), but Maudelen is not known to have been a singer, and so the theory, weak as it is, seems to founder badly.
More likely is that there was a real, notorious Windsor singer, offensive in some unknown way, who enjoyed local celebrity in the 1590s. Would Shakespeare insert a real person into the history play? Well, yes, he does such things. This sequence of Henry plays, nominally set in the early decades of the fifteenth century, is given to anachronism and occasionally introduces one of Shakespeare's contemporaries into the story, perhaps as some sort of private joke. A "William Visor of Woncote" who was very likely a member of the Visor or Vizard family of Woodmancote in Gloucestershire is mentioned by Shallow's factotum Davy. And then there's "Clement Perkes a' th' Hill," who as been traced to the Purchas or Perkis family who dwelled on Stinchcombe Hill. And also the "re-nosed innkeeper of Daventry" (Daventry is a village on the London-Coventry road that Shakspeare no doubt frequented.) These imagined beings are indulgences on Shakespeare's part that might have amused the knowledgeable but can only puzzle us. The "singing man of Windsor" would be another such bafflement.
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