I wonder if it is at all possible for anyone to appreciate Lenny Bruce if they didn't hear him live. I have just listened to his two most famous concerts at the Curran and Carnegie, and I think Bruce would have told me 'it was another generation'. He understood that his context was specific.
Lenny's voice, pacing and patter created a unique combination of artistic skills that make current day standup comedians seem artificial. He seemed to just go up there and improvise with a subtle kind of self-deprecation for his audience that was endearing. He felt like he felt and did so in sharp declarations, something that cut through to simple human emotions in a starkly honest way. Listening to him was like listening to an inner monologue that had no demons, you could say that Lenny Bruce had no filter, but what was going on at bottom was clear and sensible enough so that no filter was no problem. Lenny himself was not a weirdo haunted by memories. His stream of consciousness was reckoning with a changing society, in a context that lots of people understood, even though getting through his slang was at sometimes challenging to me.
I have some nostalgia for the flavor of ethnic humor now gone. Tsouris. He even recognized it himself, 'Schmuck doesn't mean schmuck any more'. A dozen other Yiddish terms we don't hear. That level of indirection is missing from today's humor, and Bruce presaged the possibility without lament. He understood that context was the key to making everything funny - you had to share an understanding, you can't fake a laugh.