One more thing, I don't think he ever was an avuncular, Old Uncle Gary. Someone years ago already pointed out that Keillor was subtly relentlessly mocking the Lake Woebegoners. If you didn't pay close attention, you'd think he was celebrating them. But there was always an undertone of mockery and superiority. In my view, Keillor was a deeply alienated person from high school or college onward. Alienation can fuel an artist's creative talent but can also lead to the kind of mocking, jaundiced animosity toward convention. Part of Keillor's genius was that he could interweave subtle mockery with celebration and people heard one or the other accented depending on their own orientation. Someone as skilled as he is can readily get you to overlook the little twinges of doubt that may briefly register as you listen to his chatter.
I do think he is a very talented artist, with a very inventive mind--really of the stature of Mark Twain. But he's also a deeply alienated, angry man, much like many of the leftists. The difference is that most of them have almost no sense of humor or rhetorical genius. Keillor has both, in spades.
You are quite right, although some people can't discern either. I always felt (when I listened to him years ago) who was disdainful with a flair to the people of "Lake Woebegone" and all of his growing up in the area.
His hiatus to NYC and then overseas just reinforces my belief.
FMCDH(BITS)