Dennis Miller is the pinnacle of right wing "humor.". That's about all you need to know.
I wouldn't describe P.J. O'Rourke as "right" but he's definitely not left. His tepid, anyone but Trump endorsement of Hillary: "She's wrong about absolutely everything, but she's wrong within normal parameters."
O'Rourke is pretty lame. He was kind of funny in the 70s, but he hasn't made me laugh in decades. He seems to be the only one who thinks he's funny, because he has an annoying tendency to laugh at his own punchlines. Of course, sometimes that's the only way for the audience to know it's a "joke," when P.J. chuckles at his own witticism.
At this point it's certainly a clichè, but humor has to have some truth in it to be funny. That's especially the case for satire. And since right wing tropes are so often based on stuff that isn't true at all, their attempts at humor fall flat for anyone outside the Fox News crowd. If the people who don't reside in the right wing fever swamp aren't even familiar with the false premise the joke is based on, they aren't going to laugh, they're going to be puzzled. I've seen enough right-wing memes on FB to know that they're uproarious to the typical Hannity or Fox & Friends viewer, but the rest of us just look at them and go "huh?"
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I'm having such fun watching so many late night comedy shows skewer Team Trump. (Thanks for my DVR) That said, is there any such thing as a "Right" comedian or show?
Curious how they might make humor from chaos.
Best Regards,
Ron Carter