Yurodivy, St Simeon, the ship, and the holy fool.

The Soul of the People, by Mikhail Nesterov.

From Wikipedia:

"The yurodivy (Russian: юродивый, jurodivyj) is the Russian version of Foolishness in Christ (Russian: юродство, yurodstvo or jurodstvo), a peculiar form of Eastern Orthodox asceticism. The yurodivy is a Holy Fool, one who acts intentially foolish in the eyes of men. He or she often goes around half-naked, is homeless, speaks in riddles, is believed to be clairvoyant and a prophet, and may occasionally be disruptive and challenging to the point of seeming immorality (though always to make a point).

Part of the Biblical basis for it can be seen in 1 Corinthians 4:10, which famously says:
"We are fools for Christ's sake, but ye are wise in Christ; we are weak, but ye are strong; ye are honourable, but we are despised." (KJV).

The most famous example in the Western church is St. Francis of Assisi and a more recent Western example is St. Benedict Joseph Labre. There are also parallels in non-Christian Oriental religion, notably amongst Zen monks, and the Mahasiddhi traditions.
The practise was recognised in the hagiography of fifth-century Byzantium, and it was extensively adopted in Muscovite Russia, probably in the 14th century.
The madness of the yurodivy was ambiguous, and could be real or simulated. He (or she) was believed to have been divinely inspired, and was therefore able to say truths which others cannot, normally in the form of indirect allusions or parables. He had a particular status in regard to the Tsars, as a figure not subject to earthly control or judgment.

After the 17th century the yurodivy existed more in the arts than in real life. Prominent examples are the fool in Boris Godunov, Pavel's mother in The Brothers Karamazov and Prince Myshkin in The Idiot. The composer Dmitri Shostakovich and the pianist Maria Yudina have been cited as 20th century examples of the type

From Ship of fools.com

"Ship of Fools has adopted as its patron and example the coolest saint in all Christendom – St Simeon the Holy Fool, whose Feast Day we celebrate every 21st July. For the story of his surprising life, read on. And for the stories of others who might have aspired to be his followers, read our Loose canons pages.

The desert saints of the early centuries were a wild and strange breed – and none were bred wilder or stranger than the saints of Syria. Some of them stood and prayed for years on end without sitting down. Others lived on top of pillars in the desert where they preached, wrote epistles and drew crowds of pilgrims. Numbered among these maverick saints is our patron, St Simeon the Holy Fool.

Simeon's saintly career started out quite normally. It was the usual story: 29 years living on lentils in an isolated cave next to the Dead Sea, at first struggling against temptation and then advancing to an alarming degree of holiness. But Simeon's story took a dramatic turn when he left his cave one day and set out for the city of Emesa in Syria. Arriving at the city gate, he found a dead dog on a dungheap, tied its leg to the rope around his waist, and entered the city dragging the comatose canine behind him.

This was only the beginning. For Simeon had decided to play the fool in order to mock the idiocy of the world and also to conceal his own identity as a saint. His behaviour was eccentric and, of course, scandalous...

During the church services, he threw nuts at the clergy and blew out the candles. In the circus, he wrapped his arms around the dancing-girls and went skipping and dancing across the arena. In the streets, he tripped people up, developed a theatrical limp, and dragged himself around on his buttocks. In the bath-house, he ran naked into the crowded women's section. On solemn fasting days he feasted riotously, consuming vast amounts of beans – with predictable and hilarious results. In his lifetime, Simeon was regarded as a madman, as an unholy scandal.
It was his death that the secret life of Simeon came to light. People started to talk about his acts of kindness – and about his strange and powerful miracles. There was the poor mule driver whose vinegar Simeon turned into wine so that he could start a successful tavern. There was the rich man who was saved from death when Simeon threw a lucky triple six at dice. And there was the young man Simeon punched on the jaw to save him from an affair with a married woman.

St Simeon the Holy Fool was a secret saint, his story was a holy farce, and his life shows how God chooses "the foolish things of the world to shame the wise; the weak things of the world to shame the strong" (1 Corinthians 1:27)."