I've often pondered this puzzle myself, but never came up with an adequate answer. Maybe it's just inherently difficult to make jokes about school voucher programs and tax breaks. But just yesterday, I was struck by a different thought:
What if the polarization of society has reached the point where liberals and conservatives simply have different senses of humor, and don't find each other's comedy funny?
The realization hit me when someone described the importance of Rush Limbaugh's use of humor on his talk radio show. I freely admit that I've never listened to Rush Limbaugh's radio show, but I've seen the occasional clip, and I never found him funny. So I looked up "rush limbaugh funny" on YouTube, and found a recording of his performance at the CPAC conference from a few years back. You can watch it here: https://www.youtube.com/watch?v=Gf4iwfkzbK4
I watched the entire clip, and never laughed once. Not even close. And I wasn't trying to suppress laughter; I just didn't find Rush funny, though he had an energetic and amiable delivery. At one point, he even tells a joke about Larry King going to heaven--Larry King is God's gift to comedians--and even that wasn't funny.
But, during the clip, you can hear the audience rolling in the aisles. It's full of genuine belly laughs, and the clip is from CSPAN, so you know they didn't have the budget to add in a laugh track. Limbaugh's audience found him hysterically funny.
Conservative comedy might not be funny to me, or to the effete, coastal, liberal, Ivy-league educated television and film critics of the country, but it appears to be very funny to its chosen audience.
I thought Dennis Miller was hilarious back when he was on Saturday Night Live, and crashingly unfunny as a conservative pundit. But my taste isn't the final arbiter of humor; the audience is. Many people love to trash the comedian Carrot Top, but he continues to play to sold out shows. Many others mock "The Big Bang Theory," but it remains the top-rated comedy on television.
More to the point, saying, "I don't find Rush Limbaugh funny, so he obviously isn't funny," is the semantic equivalent of saying, "I don't enjoy listening to rap, so it obviously isn't any good."
I don't have to agree, approve, or even condone someone else's point of view. I can and should contest mistaken beliefs with facts and logic. But I (and you) should start with the premise that most of the people you disagree with have honest and sincere reasons for their beliefs, even if they are wrong--after all, shouldn't they assume the same about you?