Leading upper-case Cynic philosophers exhibited a lot of behavior that might be called lower-case cynical today.
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.
If Diogenes was doing an act he was really into it.
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.
So, assuming this isn't just a rumour spread by Diogenes himself....
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?
Well if he had zero money he couldn't retire to a quiet country life... That's why homeless people today do not choose to live in nice places in the countryside but instead sleep on the pavement in cities. It's much less pleasant but you starve less in the city.
Also, maybe he wanted to tell other people they were fools, not just "wanting to be seen not giving a fuck".
Sure, if you want to lecture people about themselves then you give a fuck about at least that, but it's different than simply trying to be the center of attention.
I really think Diogenes was a philosopher (Diogenes the character -- this is true whether he actually existed or not): he had a point of view that he wanted to share.
Diogenes (the character) was a famous, upper class dude. Lifelong poverty wasn't a trap he couldn't escape.
Also I didn't mean to be too harsh. The "can't wait to tell you how little I care" trope is one we can't escape even in modern dissident youth culture. Hippies, punk, goth, emo... every generation reinvents it and it's artistically/culturally rich ground.
That said, the Diogenes character definitely does seem like he enjoyed being the centre of attention. It's like Marilyn Manson going on daytime talk shows in the 90s to tell normies that he doesn't care what they think. There's obviously a falsity in there, somewhere. It got my attention though, as a teen, and I still listen to th albums.
The point of the barrel is to be seen in a barrel, at the very least to demonstrate the philosophical reasoning for the barrel.
There are plenty of people who genuinely don't care what the people of Corinth think, say or do. The don't choose to spend their time in the public square debating.
This "care what you think" phrasing I think is really deceptive. Because the active issue is whether you conform to group norms or refuse to do so.
If someone refuses to conform to a group, then demonstrably they don't care enough about the benefits of group inclusion to comply with the group demands.
If someone quits their job, they may in _some_ sense "care what the boss thinks," but there is a much more important sense in which they don't (while those who do not quit, do).
I guess people may be "loud" about their refusal, in various ways, because they don't want a refusal to conform to be mistaken for an inability to perform. Much like the person who is quitting does not want to be perceived as having been fired. Again, that is a very different kind of concern than the person who is trying to keep their job.
There can be cultural moments, relationship moments, etc. where the exact same thing may register as a lame "can't wait to tell you how little I care" or a much needed bit of stridency... a la chuck berry, john lennon or courtney love.
Edge Lord is the pejorative to something with a very flattering synonym, though we might argue what that synonym is.
> 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).
Many historians think this anecdote is apocryphal, giving credence to the opinion that Diogenes' act was... an act.
A lot of this is probably apocryphal. He was such an outrageous character that people seem to have used him as a trope when telling jokes, he was a living fictional character and seems to have enjoyed fanning on the stories about him. This is sort of central to the accusation too, he seems to have really reveled in his infamy and no doubt encouraged these stories.
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.