Critical analysis doesn't concern itself with the effort the creator put into an image, just that the image is there and readable, and follows a certain logic the critic decides on. But besides that, Norm Macdonald is an art house comedian with a love of genre jokes, he's most definitely put more details into jokes and their meaning than I could gather. Critical analysis is about the viewer finding meaning in art, from whatever their view point is.
I agree with everything Norm was saying, and there's a sea of difference between what he's doing and the "metahumor/anti-humor" he was criticizing. He's not being ironic, he's not purposely telling bad jokes where the joke being bad
is the punch line. No, his brand of humor is about the journey, not the destination. His delivery. He puts in a lot of effort into making people laugh, and as you see in those Conan clips, people are laughing all along the way, way before the punch line. The punchline isn't important to his jokes, but that doesn't mean that he's purposely being bad or half assing anything.
I find the whole "anti-humor" label a misnomer anyway. Are these comedy shows? Do people that enjoy them find them funny? Is the intent of them to make people laugh? I would think it is. Ergo, what these people are doing is merely comedy, not "anti-comedy." If their intent is to be unfunny, then clearly they are failing, since lots of people find their stuff funny. And Andy Kaufman was doing this shit decades ago, no one was calling it anti-humor. It's all bologna.