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Ricochet Editor Jon Gabriel attended a humor panel at the progressive conference Netroots Nation 2014 a few weeks back which he documented in a short but brilliantly insightful piece into the mind of the perpetually angry, titled 
You mentioned Skeksis. And it was employed so well.
Capital, sir. The left is even totalitarian about humor. And they’ll clap you in irons if you don’t laugh hard enough – or foolishly laugh at the wrong people.
My favorite part about telling a joke to a progressive is the two-second pause as his brain processes the language to see if he’s allowed to laugh.
There are SO many unwritten comedy sketches about modern Democrats/liberals. I sometimes think about Ricochet members getting together and writing some humorous bits critical of modern liberals or the Obama administration. No one is doing that right now, and all this funny stuff is just left on the table. Their mischaracterization and scorn for the right grows more and more absurd, the comedic material writes itself at times. We should start really making fun of them! The closest thing I saw in recent years to successful teasing of liberals was actually Mitt Romney’s speech at the Catholic dinner or whatever it was, just before the election. Find they guy who wrote that and get him a show!
Your description of liberal women was spot on. My wife and I are still laughing. :D
This might be the best thing ever written diagnosing the humor/politics problem.
Watch Last Man Standing on ABC, Friday nights. Tim Allen is the star and it is awesome. They actually tell right wing jokes, i.e. rip on Lefties, and they are .. wait for it .. funny. Yes, certainly on of the funniest shows on network TV. No sex jokes or dirty stuff, just good clean Liberal bashing. He almost makes it look to easy.