I was struck by the thought on reading King Lear. That is set in ancient Britain but anything about jesters/court fools from throughout history would be much appreciated.
Would they have had families? How were they chosen? Are there instances in which they have been portrayed that are particularly accurate/inaccurate? What are the best sources for finding out more?
You might be interested in some previous threads on court jesters from the FAQ section entitled "Court Jesters" as well as a recent search:
The Life and Occupation of Court Jesters
Notable Jesters
Vicki Janik's introduction to the book I mentioned in my other comment touches on the some of the concerns I had in relation to fooldom:
In ancient Greece the fool-parasites charmed the wealthy into offering them dinner invitations with the promise of entertainment and joking. One step from being beggars, they exploited their own pretended or real infirmities for food and money. Welsford describes the existence of such figures in Greek and Roman society. Nearly two thousand years later in the courts of Europe, natural and artificial fools still were supported and often entirely maintained by the wealthy. Many courts, including that of Peter the Great, the early-eighteenth-century czar of Russia, kept great numbers of natural and artificial fools. In order to maintain the size of this group, his court went so far as to arrange marriages and funerals for naturals such as dwarves who were wed in grotesque mock ceremonies. Thus, like the jokes they told, natural fools seemed spontaneously to generate and to be forever maintained agelessly; where they had been and when they had left were either unanswerable questions or irrelevant ones.
Even very famous fools in society lack clear ties to the real world and seem to be at odds with "normal" existence. Will Sommers was born, according to Robert Armin's verse, "in Shropshire, as some say / Was brought to Greenwich on a holy day, / Presented to the king". His heritage is questionable: meager references to family, like that to an "onckle," may be only fictional, having been recorded by Armin from traditional jokes. Armin also writes that while Sommers dined with the king and Cardinal Wolsey or jested with the king alone, he later "laide him downe among the spaniels to sleepe". Such contradictory, atypical experience is representative of the fool. Modern, real-life fools sometimes live similarly unfocused lives. Douglas Brode contends that Woody Allen's persona has penetrated into his private life and is at odds with the private life he tries to live. Although Allen's experiences have been more acutely painful, they reflect the confusion surrounding the private lives of Groucho and Chico Marx. The necessary peripheral objectivity and isolation of the fool perhaps make the intimately shared life of marriage and family difficult.
Fools and Jesters in Literature, Art, and History A Bio-Bibliographical Sourcebook ed. Viki K. Janik pp.8-9.