Harry, as usual, has a lot for us to think about. We can start with this video and related Caucus item. Which made me think of this article. (I confess, I think the article somewhat conflates irony with all humor.) I mean, irony has been kind of the province of the left, but Obama -- who draws out sincerity from us -- kind of invites a newly non-ironic stance.
Meanwhile, as Harry has rightly detected, it isn't really true that the conservative media is not funny. Some of hem have to be funny, but differently funny.