Keillor’s humor has always been a bit of a puzzle: What is its irony/sincerity ratio? Is he mocking Midwesterners or mocking the rest of us via Midwesterners? In 1985, when Time magazine called Keillor the funniest man in America, Bill Cosby reportedly said, “That’s true if you’re a pilgrim.” A decade later, a cartoon version of Keillor forced Homer Simpson to assault his TV and shout, “Be more funny!” –Sam Andeson —A Prairie Home Conundrum: The mysterious appeal of Garrison Keillor. (Slate)
A great quote from later in the piece: “Without saying it outright, Keillor projects himself as a sage — a kind of Wobegon Obi-Wan spreading the revolutionary creed of premodern simplicity.”
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Yes, there's a gentleness and restraint about the humor that walks the line between ironic self-awareness and complete honesty. I realize that's an act, but it's very effective for his style of humor.
I'm always amazed at Keillor's very nuanced humour. I don't think really he's making fun of anyone. I think he skillfully makes exaggerations of reality. The show (Prarie Home Companion) also says a lot about human nature. And, in essence, that's what makes it so funny.