I think the main issue is conservatives don't understand humor and never have. This is why there are so few successful right wing comedians but so many successful liberal ones.
Humor can be and should be transgressive but what conservatives never get is the HUMOR comes first, and transgression second. To illustrate you should listen to Carlin's bit about how he likes it when a lot of people die. It's funny because it shows how we claim to hate death and destruction yet we can't watch or read enough about it. You aren't supposed to admit that though. 'I hope you are assassinated because you support Palestine' isn't funny because there's... no joke there.
They don't get it. They can't tell the difference between racism and racist jokes. You can make jokes that are racist and funny. Colin Jost and Michael Che do it all the time on SNL and they are very funny. Look it up on YouTube.
There is a time and place for jokes. Politicians are not comedians and they have no place telling racist jokes, in the context of a contested campaign. George Lopez told a Hispanic joke where the premise was this is what they say about us. What was said at the Trump rally? Puerto Ricans are garbage. There were also non comedians that said racist shit and all of it was vetted by the Trump campaign.
They keep crying people shouldn't get so offended. Remember the Al Smith dinner that Harris turned down? What if she did attend and said the following...
I'm so glad to be at this dinner to prove we can all take a joke. I brought a guest with me the porn star Rocco Siffredi (turn towards Malania) you know, Melania in case you wanted to get a little payback.
Question: Would not conservatives have the biggest meltdown in history?