This is, I believe, the crux of what makes it so hard to have conservative humor. So much of conservative humor is focused on ridiculing the victim. That’s inherently unfunny. And it’s also true that today’s conservatives are much angrier than those of even a decade ago.
Because it’s so hard to be funny as a conservative, I remember some of the jokes by right wingers that I thought were at least somewhat funny.
To be funny, conservatives could use self-deprecation. I remember George W. Bush speaking in front of a bunch of ultra-wealthy people. He described his audience, which was wealthy bankers, oilmen and such and he called them “my base.” It wasn’t hilarious, but it was funny. And his delivery was quite good.
His father showed another way to conservatives can be funny—non-political humor. I know this is a cop out (at least a bit) but it does show that conservatives can be funny. There was a tabloid that had a picture of a space alien who, the tabloid said, originally endorsed Bush for the coming election, but then switched to Clinton. George Bush (senior) said very dryly: “I never did trust that little guy.” I found that very, very funny—in large part because the elder Bush didn’t tell many jokes.
But overall, conservative humor is saddled with the perspective that they need to ridicule the downtrodden and the victims. And that’s just not funny.