Jon Stewart hasn't changed, and that's the problem. As far as his comedy, no notes. He's undeniably funny. But his politics just leave a sour taste. His enlightened centrist voice of reason shtick hits different now.
He's defended people like Rogan and Chapelle. And I get it, they're his buddies. He doesn't see them as public figures, but as flawed individuals. And that's a valid perspective, just a rarefied one.
His first guest upon his return was the editor of The Economist magazine who gushed about Reaganomics and Thatcherism. She framed the rise of right-wing politics in the West as first and foremost a threat to the neoliberal world order as Jon nodded along. And we all know that progressiveism is just the other side of the horseshoe to people who think this way.
I'll be watching Stewart, and I really do admire him. But never meet your heroes I guess.
I agree with pretty much everything you've said.
I think where we deviate is on why we examine right wing talking points in good faith: not because they might secretly be right, but so we can genuinely understand what what people believe so that any counter-position that we form can be formed against the version of the argument that they believe.
There is no point in constructing a counter argument against our version of an understanding of a position if it isn't what thiers is, from their perspective we're skewing a strawman that doesn't align with their perception anyways. It's simply a masterbatory exercise at that point, with no persuasive value.
The responsibility, unfortunately, is on the informed to persuade the ignorant that there are systemic issues that have to be resolved to address the in-progress cataclysm. There, unfortunately, isn't an alternative in which the world as we've come to understand it isn't destroyed.
In short: we can't afford to silo ourselves and dunk on the right for the purposes of getting mad props from the people who already know the score. It might be self gratifying, but it doesn't do anything to resolve the societal issues that are allowing this train wreck to unfold.