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Bill Burr is a surprisingly thoughtful and principled guy with consistently good opinions. He’s a comedian, and he doesn’t have any theory underpinning his worldview, but I bet if you look at why he’s been criticized in the past it’s by liberals who are mad that he’s being critical of liberals. I’m not at all surprised that he lit up Bill Maher on his boomer-ass Israel-Palestine takes.
Making generalizations about people is a problem when the generalization is false or misleading, or is being used to make a false or misleading argument, which is often the case. If you’re wondering if a given generalization is problematic, odds are the answer is ‘yes’ otherwise you probably wouldn’t think of it as a generalization.