|Mokey McNeilly, chief loon for SNL Helena|
First and foremost you have to really empathize (imagine another's view) in order to "get" satire. Furthermore satire must be based on the truth. You can say all kinds of weird things, but only something that points up a real truth will be believable and–with an odd angle of approach–funny. Also you have to have a flexible mind in order to find something funny, otherwise it's just wrong or insulting. And finally you have to be able to see a wider context for the subject. (Which is why a joke takes a certain set-up: to establish the context.)
Unfortunately conservatives–intelligent though they may be–do not tend in these directions (I realize I'm over-generalizing). They have a harder time showing concern outside their own group; tend to fudge the truth to get their preferred results, have a harder time seeing metaphoric connections (which makes for irony) and have a narrower worldview. Thus their difficulty in producing comedy. (Irony plays a huge role. In one highlight of our show, Mokey simply read the text of a bill verbatim. The originator of the bill was blind to the contradictions inherent in the bill!) It's instructive that many don't understand that the reason Steven Colbert is so hilarious is he's being ironic. I'm not being mean here, just trying to look at facts.
Just as a child grows into a wider sense of the world that informs and undergirds their sense of humor, adults grow into their complexity. Some develop flexible, tolerant, creative minds that allow for humor and we tend to see liberals. Others don't and we call them conservatives. So then the next question for me is are there ways where a conservative mind is more capable than a liberal one? If so, how so?
It gets more interesting the deeper one digs here.
In A Conservative Walks Into a Bar: The Politics of Political Humor, Alison Dagnes concludes that conservatism is philosophically incompatible with satire. “The nature of conservatism does not meet the conditions necessary for political satire to flourish: conservatism is harmonized and slow to criticize people in power, and it originates from a place that repudiates humor because it is absolute.” Part of the reason why political satire is liberal is that liberals try to topple the traditional power structure (humor is just another tool) while conservatives uphold it (it's to power's advantage to not encourage such humor). But much as this explanation helps, it also hides a deeper issue.
In comedy laughter releases an underlying tension. Let's compare two comedy bits on gun control. On the "liberal" Daily Show bit on Ferguson. The underlying tension is the frustration of racial targeting for abuse, shared by not only minorities but empathetic people who can imagine and sympathize.
Compare that with a segment of the "conservative" 1/2 hour News Hour, (a Fox News attempt at replicating the Daily Show). Here the subject, a gun nut, turns out to be a criminal afraid of the police. Here the underlying tension driving gun control (living in a society where any loony might have a legal concealed gun in public) is replaced with the comparatively miniscule tension resting on fear of law enforcement having guns. It's a bad trade. The only laugh comes from the surprise that he's a crook, unless one believes that gun-control advocates are simply afraid of guns.
So even though the theme is shared–fear of those with guns–the tension from the first bit is much more universal and "true" (fewer people fear law enforcement than "people with guns"). If the butt of the joke is a subject which doesn't include native tension but a manufactured one, the laugh will be flaccid.
I would say great satire is largely about hypocrisy. Indeed one of the criticisms I hear from the conservative side is that liberals are hypocritical. Yes, but that is usually only true on the surface (I'm talking about high-quality work here, not just the normal fare). While a conservative sees a contradiction in "global warming" by pointing out a snowstorm, they do so by ignoring the deeper pattern, in this case the slow warming that is too subtle for our senses; the kind of tension that spurs a liberal satirist. While great satirists poke fun at human foibles the lessor players have a hard time separating persons from behaviors. The former is where some cheap laughs are, but not the enduring ones. In the end the really timeless laughs are not about the other fool, but about the fool that is ourselves.