Jackie Mason has been funny at times over his long career, but is mostly just a bitter old right-wing crank now. Colin Quinn is conservative. He used to do a show directly after Jon Stewart that was just...such a painful contrast. He and Dennis Miller should do an unfunny-off sometime. Not a comedian, but some say PJ O'Rourke is a funny writer; I have yet to be convinced. I have no doubt that Dice Clay votes Republican, if he votes. (There are also programatically liberal comedians that are not funny, like Will Durst.) Maybe it's that a conservative mindset blocks the kind of unexpected associations and reversals-of-perspective that make for humor; it seems to me equally possible that the kind of literal, unnuanced, black-and-white mindset that generally seems to make a sense of humor unlikely also makes one more likely to be conservative. These are all very broad generalizations, of course. I have a conservative Republican brother who is a very funny man.
