Holy fools subvert prevailing orthodoxy and orthopraxis in order to point to the truth which (sic) lies beyond immediate conformity. The Concise Oxford Dictionary of World Religions
“Our nation demands the scrutiny of a completely disengaged observer like your Working Boy, and I already have in my files a rather formidable collection of notes and jottings that evaluate and lend a perspective to the contemporary scene.” Ignatius P Reilly, A Confederacy of Dunces, John Kennedy O’Toole
In the literary landscape of the West, from the plains of ancient Troy to the streets of contemporary New Orleans, Wise Fools have thumbed their bulbous noses at decorum and provided contrarian views against the cultural status quo of their respective milieus. Armed with wit, not weapons, these outsiders can see beyond entrenched hierarchies and customs, and historically, in the employ of a king or queen, court jesters (or licensed fools as they were sometimes called) could in frankness utter truths that a higher individual dared not.
On the literary side of the ledger, let’s look at Thersites from The Iliad, that bandy-legged malcontent, “a menial, a nonentity among dynastic aristocrats,” according to C.R. Beye.
But wait. What are these “dynastic aristocrats” up to? Waging a ten-year war to avenge someone’s wife running off with someone else’s husband. And ultimately, it’s the gods’ fault anyway, the Judgment of Paris and all that jazz. With the hindsight of a couple of millennia, waging a decade-long war because of elitist adultery seems even dafter than the post 9/11 invasion of Iraq.
When the Iliad begins, the siege is at a stalemate because King Agamemnon, the alpha male of the Achaeans, has usurped Achilles’ war spoil Briseis. Even though Achilles is his best warrior, his LeBron James, Agamemnon gets dibs on (forgive me) Achilles’ booty because he’s higher on the totem pole. Achilles retreats to this tent to pout (the equivalent of LeBron benching himself) while swords clash and “night descends upon the eyes” of warrior after warrior slain in the service of trying to retrieve runaway Helen, whose face (aided and abetted by other bodily parts) “launched a thousand ships /And burnt the topless towers of Ilium.”
Thersites recognizes the absurdity of the war and the unfairness of Agamemnon’s receiving “the lion’s share of the spoil” while “Achilleus (sic) does the lion’s share of the fighting.” 
Although despised by the soldiers, Thersites wisely advises them to abandon the war, to return to their homelands, to their own wives and children, so they can teach Agamemnon a lesson.
He confronts Agamemnon directly:
Your shelters are bulging
With bronze, and whenever we sack a city you always
Get the choicest booty, including whole bevies
Of beautiful women. Can it be you still want gold,
The ransom some horse-trading Trojan brings out of Troy
To pay for his captured son whom I or some other
Achaean bound and led away? Or would you
Prefer a ripe young lady to sleep with and keep
Shut up somewhere for yourself? Truly, it hardly
Becomes their commander to burden with so many troubles
The sons of Achaeans.
Translated by Ennis Reese
Perhaps because his physical hideousness has alienated him from the heroic slaughterers who surround him, Thersites recognizes the absurdity and unfairness of the heroic ideal.
Thersites also appears in Shakespeare’s Troilus and Cressida, one of the so-called problem plays. Like his ancestor in Homer, the 17th Century Thersites is hideously ugly but much wittier than his counterpart in The Iliad. He’s a king of vituperation who out-Don-Rickles Don Rickles. Here he is suggesting that old, supposedly wise, Nestor’s mind has seen better days:
There’s Ulysses and old Nestor, whose wit was mouldy
ere your grandsires had nails on their toes.
When Ajax threatens to cut his tongue out, Thersites replies, “’Tis no matter! I shall speak as much as thou afterwards.”
And what a rich source of insults: loathsome scab, sodden-witted, scurvy-ass, idol of idiot worshippers, full dish of fool, idle immaterial skein of sleave milk, green sarcenet
flap for a sore eye, tassel of a prodigal’s purse, waterfly.
Agamemnon, he says, has “not as much brains as earwax.”
Of course, the wisest of all of Shakespeare’s wise fools is employed by Lear. Unlike the two Thersites, Lear’s Fool’s wit, though sharp and biting, is noble-minded. He loves the king and speaks frankly to him, trying to point out to Lear his own foolishness.
Fool: That lord that counsell’d thee
To give away thy land,
Come place him here by me-
Do thou for him stand.
The sweet and bitter fool
Will presently appear;
The one in motley here,
The other found out there.
Lear: Dost thou call me fool, boy?
Fool: All thy other titles thou hast given away; that thou wast
Shakespeare, of course, did not invent the court jester, or licensed fool, as they were sometimes called.
Here’s a brief history from the blog Under the Tudor Rose:
In ancient times, courts employed fools and by the Middle Ages the jester was a familiar figure. In Renaissance times, aristocratic households in Britain employed licensed fools or jesters, who sometimes dressed as other servants were dressed, but generally wore a motley (of mixed colours or materials) coat, hood with ass’s ears or a red-flannel coxcomb and bells. Regarded as pets or mascots, they served not simply to amuse but to criticize their master or mistress and their guests. Queen Elizabeth is said to have rebuked one of her fools for being insufficiently severe with her. Excessive behaviour, however, could lead to a fool being whipped, as Lear threatens to whip his fool.
His is not an enviable position in that most dysfunctional of households.
Fool: FooI [i.e. Lear] marvel what kin thou and thy daughters are. They’ll have me 705
whipp’d for speaking true; thou’lt have me whipp’d for lying;
and sometimes I am whipp’d for holding my peace. I had rather be
any kind o’ thing than a fool! And yet I would not be thee,
nuncle. Thou hast pared thy wit o’ both sides and left nothing
i’ th’ middle. Here comes one o’ the parings.710
The most famous of these fools was Will Somers, Henry VIII’s court jester. Perhaps because of their unequal social status or that fact that Somers didn’t try to capitalize on his relationship with the king, Somers and Henry developed a genuinely deep friendship, though the most often quoted anecdote is that Henry threatened to kill Somers with his bare hands after Somers called Anne Boleyn a “ribald” and princess Elizabeth “a bastard.”
After Henry’s death, Somers was reduced as a sort of a comical sidekick to Queen Mary. His last public performance was at Elizabeth’s coronation.
The idea of a ruler employing a wise fool to leaven the ruler’s ego seems like a good idea to me. Obama and Chris Rock would have made a dynamic duo, and how wonderful would it be to have Louie CK try to deflate his fellow vulgarian Donald J Trump’s gaseous ego.
Although by far not the grandest, my favorite wise fool is Yeats’ Crazy Jane. Yeats based her on a local character called Cracked Jane who wandered around County Galway when he lived in his tower, Thoor Ballylee, near Gort. The great great great granddaughter of the Wife of Bath, Crazy Jane has nothing to fear from middle class censure so when a bishop chides her for her licentiousness, she provides him a little lesson on bodily matters:
I met the Bishop on the road
And much said he and I.
`Those breasts are flat and fallen now
Those veins must soon be dry;
Live in a heavenly mansion,
Not in some foul sty.’
`Fair and foul are near of kin,
And fair needs foul,’ I cried.
‘My friends are gone, but that’s a truth
Nor grave nor bed denied,
Learned in bodily lowliness
And in the heart’s pride.
`A woman can be proud and stiff
When on love intent;
But Love has pitched his mansion in
The place of excrement;
For nothing can be sole or whole
That has not been rent.’
So let’s raise a glass to the dispossessed, those unworthies who wear white after Labor Day, who don polka-dotted blouses with plaid skirts, who, to paraphrase my favorite line from Apocalypse Now, are beyond our lying, timid moralities, who are willing to call a king or bishop or president a jackass to his face.
From “Thersites in then ‘Iliad’” by N Postlewhaite published in Greece and Rome, 35.2, October 1988.
The best poetry teacher I ever had.