But with Keillor’s retirement, Americans lose something else, equally valuable and increasingly rare: a cultural figure fluent in the worldviews of both progressives and conservatives. Raised as a fundamentalist Christian in a small Midwestern town, Keillor crossed a vast ideological chasm during his career, becoming a stalwart political leftist without forgetting his small-town roots. Through his novels, his poetry, and his public-radio show, he’s served as a cultural liaison between red and blue states, interpreting each for the other, and offering a humorous, if not sympathetic, glance in both directions. His stories of life in rural America transport his listeners into a world where those of different beliefs and backgrounds exist in a surprisingly similar fashion to themselves.
For all its political implications, A Prairie Home Companion has always been about nostalgia, first and foremost. The director Robert Altman’s final film of the same name describes it as “a live radio variety show, the kind that died 50 years ago, but somebody forgot to tell them.” Keillor—who remained in his home state as he made the leap from college radio to a professional broadcasting career in the late-’60s—is unabashed about his origins, his beliefs about manners, morality, and what makes America a good place to be from. He sings patriotic ballads loudly and unironically.
While much of Keillor’s work draws on his family and childhood, the rest comes from his experience as a Minnesota writer seeking acceptance among New York’s literary elite. His life goals even as a young boy had much more to do with New York than Minnesota. Indeed, it was a 1973 New Yorker assignment about the Grand Ole Opry that planted the seed for A Prairie Home Companion, which debuted a year later. Keillor could have easily stayed in New York and pursued literary greatness there, and during his brief hiatus from the radio show in the 1980s he tried to do exactly that. But when his daughter was born in 1997, he elected to move back to Minnesota to be close to family.
Perhaps because of this sort of dual citizenship in two cultural spheres, Keillor has frequently veered far to the left of his conservative childhood on many political issues. In his 2004 memoir/manifesto/screed Homegrown Democrat, Keillor memorably described George W. Bush as an “Etch-a-Sketch president with a voice like a dial tone, a dull and rigid man suspicious of the free flow of information and of secular institutions in general, whose philosophy is a jumble of badly sutured body parts trying to walk.”
On his radio show, Keillor generally leaves politics to mild satire of famous caricatures, typically offering equal time for barbs aimed at both parties. When Al Gore won a Nobel Prize in 2007, Keillor wrote a skit in which the younger Bush sparred with Gore over the number of votes the Nobel committee actually awarded him. Keillor also regularly spends time talking about the political divisions between normal folks, as with a 2012 “Catsup Advisory Board” ad, in which a bleeding-heart liberal and a bitter bootstrapping conservative quietly bickered over politics. When Keillor travels to red states, he writes skits and songs that highlight their points of local pride (only to gently rib them when he leaves). In a recent op-ed for the Houston Chronicle he noted admiringly,
When I stopped in Lubbock, I knew where I was. The city went 69 percent for Mitt Romney, 28 percent for Barack Obama. But I don't feel like an alien there. I admire old windmills, I’m curious about prairie dogs, and I’m a fan of Buddy Holly. To me, he does not fade away. And I feel enriched by biscuits and gravy.
The thing with politics, Keillor says, is that the “guy from Lubbock” has to live in this country, too. Such a compassionate view of one’s political opponents is rare. Left-leaning, politically active personalities are as ubiquitous in public radio as pledge drives, tote bags, and Hamilton aficionados. But Keillor has always stood apart with his bizarre blend of liberal tenacity and Midwestern aplomb.