Hank Stuever, Washington Post - The No. 1 best thing about Letterman and his late-night show — then and now, the thing we’ll probably end up missing most and root around YouTube years and decades hence in a quest to recall — is his Indiana-raised insouciance. We came to believe firmly, after so many magazine profiles that tried to crack the code of Letterman’s personality, that the secret to his success was to be found in his skepticism and casual indifference to hype. His challenge to celebrity status, folderol and ballyhoo is seen as a deeply Midwestern trait.
Even if it was mostly an act, that was okay, because we also understood the air quotes around his shtick; he also helped us understand the hyperbolic air quotes around our junk-culture lives: “politics,” “movie stars,” “fame,” “news,” “popular” and “comedy greatness.” For Letterman, the gee-whiz regard for spectacle is tempered by an instinctive worry that it’s wrong to show off. We responded to the dark and cynical sides of his personality that we might ascribe to the ancestral settlers and farmers of the American Midwest whose self-reliance led them to distrust even the weather....
Letterman’s sense of irony was more than just a path to humor; it was one of the first and most dependable shields against a coming onslaught of celebrity rule. Are you like me? he would ask, all the time, setting up jokes from a place of folksy bewilderment at life. (“Are you like me, do you like science?” “Are you like me, do you like cheese?”) The answer we gave back to Letterman was yes. We were like him, or wanted to be. We knew that his mix of casual cheerfulness and skepticism would keep us safe.
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