A criticism that is as old as Diogenes (at least Laertius) is that they were essentially a cult of edgelords. They pretended not to care what people thought, but it was just an act, at the same time it was really important to them that people around them knew how little they cared through all the shockingly (lower case) cynical things they said and did. DL has Plato accuse Diogenes of this directly. All this is reducing a philosophy to a trope, but it's not an entirely unfair accusation either.
Speaking of which, a bizarre and entertaining piece of history is Lucian's extremely hostile biography of Peregrinus Proteus.
He famously told Alexander the Great to fuck off and stop blocking the light (which leads me to think that the ultimate "fuck you money" is to have no money at all, and not want any).
He would also walk around the market and masturbate in public, which the Athenians found disgraceful. When challenged about this he would reply: how happy would we be if we were able to suppress hunger simply by rubbing our belly.
I really love this character.
Diogenes' barrel was in the middle of Corinth, where he could be seen & talked about. Where he could be vocally cynical of other people, etc. If Diogenes really wanted to be left alone, fill his belly and nap... he could have done this easily.
Many Greek well-to-dos in his place did just retired to a quiet country life where no one bothers you. He didn't, wanting to be seen not giving a fuck.
I wonder if like modern counter cultural figures, his fan base tended to be late teens?
Many historians think this anecdote is apocryphal, giving credence to the opinion that Diogenes' act was... an act.
Like the exchange with Alexander, which is questionable if it ever happened or whether it's just an anecdote that went "viral". A tale of how the world's most powerful general hashing words with the world's most impudent homeless man, it's both entertaining and inspires the imagination. A bit like a superman vs batman fight.
