This mightn't be exactly what you're looking for - but Leatherman seems an example of a class of people called 'Holy Fools'. (maybe because Leatherman carried a little prayer book)

The Holy Fools were semi-religious figures who acted strangely or pretended to be mad to challenge social norms and express spiritual truths.

They were common in Russia at one time and called: "yuródivyy"

In the West, some examples would be Francis of Assisi and Benedict Joseph Labre.

edit: In the USA I'd nearly call Johnny Appleseed one of the 'Holy Fools' and even Chris McCandless (Into the Wild)

Not an official list, but there’s a few I’m aware of, each interesting in a different way.

https://en.wikipedia.org/wiki/Emperor_Norton https://en.wikipedia.org/wiki/Timothy_Dexter https://en.wikipedia.org/wiki/Eddie_Chapman