Why do conservatives have such a hard time with humor? Just take a look at this clip from the new Daily Show wannabe on Fox News, The ½ Hour News Hour, produced by 24's Joel Surnow. It generates a few half-chuckles, maybe, but it's basically just lame.
Yes, this is a serious question.
And no, I'm not saying there aren't funny conservatives. Just that, generally speaking, "conservative humor" tends to be an oxymoronic term.
Sometime early in the Clinton presidency Rush Limbaugh appeared on David Letterman. Letterman was pretty generous (as opposed to his more interesting, confrontational approach to Bill O'Reilly), and lobbed some easy setups Limbaugh's way. Though Limbaugh obviously considers himself to be a witty fellow, he ignored them. The whole segment wasn't even amusing, just weird. Limbaugh gave a skeptical, somewhat bemused audience his take on Hillary Clinton. Letterman did his "dumb guy" impression.
One answer is that a sense of grievance underlies much of the conservative media. Limbaugh, Fox News and many in the right-wing punditocracy trade on the sense of being excluded and demeaned by elites, who are thus deemed to deserve nothing but scorn and mockery. So their attempts at humor - at least, the ones that get broadcast - tend to be pretty blunt and obvious, sometimes mean-spirited. That is, not funny. Dennis Miller seemed to lose it when he put himself in the Bush camp and started announcing his fervent desire to blow our enemies up. Ha ha!
Surnow, to his credit, seems to recognize that harshness doesn't do it. But he's got a long way to go.
So how is it liberals - at least some of them - are funny? The idea that there must be a "liberal humor" vs. "conservative humor" smackdown is the same false dichotomy you find comparing "Doonesbury"and "Mallard Fillmore." "Liberal" may be a degraded term in the political sphere, but In America today "liberal" is a broader, more protean category than "conservative." Jon Stewart is a liberal, but neither he nor the Daily Show view things purely through a left-wing prism. Their goal isn't the care and feeding of a single, narrow political constituency. Thank God.