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Jon Stewart is pundit who is a comedian. He self-identifies as a comedian because he knows that he’ll be viewed as less polarizing that way and thus will lure a bigger audience. His humor is also a nice capsule into which he can fit his left-leaning ideology. People resist messaging if given it dead-straight; humor is disarming and laughter is catching. It’s an excellent way to break down an individual’s resistance and make them more susceptible to hearing out your message.
Stewart is enough of a pop culture icon that he can arbitrate what is or is not funny. Since Hollywood is dominated by enough progressives who approach comedy in the same vein, it makes a strange sense that a progressive can crack a racial joke at the expense of a black conservative and it’s comedy – but it only works within the arbitrary comedic paradigm which dictates black conservatives cannot exist.
I get it, it’s the meeting of comedy and punditry, which is what Stewart’s show has progressed into, away (unintentionally, I think) from “humor-news.” That, to me, is his real achievement: irony isn’t dead, it lives on every night, its purveyor unaware, on “The Daily Show.” Unless, of course, it’s intentionally lampooning the bias of mainstream media in a Kaufman-esque way.