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I love comedy podcasts, The Jeselnek and Rosenthal Vanity Project, a favourite. His style is dark humour and it seems that a significant proportion of the audience actually believe some of the things he jokes about. I think it's one of the reasons they rarely field audience questions and never phone calls.
Comedy can be a minefield for this type of stuff. I'm a big fan of the comedians that can dance around the edge, or seem to cross it and then bring the audience back, eg: Mark Normand, Bill Burr, Jimmy Carr, a lot of the old Norm MacDonald stuff, etc.
But I'll see some fan compilations with titles or comments that make it clear that they don't get the style of humor... Like "[comedian] DESTROYS feminists!!1!"
When, to anyone with a reasonable level of social intelligence, it's abundantly clear that that's not what's happening.
Yeah, those guys are walking the high wire and making it look easy. One slip could result in a Dave Chappelle.
I really thought Chappelle was one of those people but yeah, he refused to step back from the edge.