In an interview with The New York Times about his final broadcast on May 20th, David Letterman attributed part of the reaction to his upcoming departure to artificial reverence. And—to a degree—that’s true. No one has died.
But we’re also talking about a man who once decided to have one night on his show be “camera night” and filled with the studio with over 13 cameras. (His show usually only had about three to four.) This is a man who decided to rent a 747, fly to Miami, and film a whole show on the airplane on the way to Miami. He got Buzz Aldrin to do fake red carpet coverage of the Daytime Emmys, with the astronaut berating the actors by reminding them again and again and again that he had walked on the moon. Letterman hosted the the show where Tom Waits told a story about a horse cribbing a picture of a horse jumping over a fence. He hosted the show in which cameras started following a cat around the studio mid-segment, and when Letterman headed up to the control room to see what exactly is going on, he found that the control room had been overtaken by dogs.
Letterman was the guy from Indiana who became a weatherman then went to L.A. to pursue stand-up comedy, who landed a spot on his idol Johnny Carson's show and then launched out on a show of his own that set to ironically deconstruct the format on which he grew up.
Why else would you see Conan O'Brien begin his run at Late Night with a montage of New Yorkers hectoring him in the street with the constant refrain of “you'd better be as good as Letterman?” (In response to the challenge, Conan tried to hang himself.) Even David Foster Wallace wrote a short story about an actress who went on Letterman—and who was told by many to be “afraid” of Letterman—only to be surprised by the fact that he was actually a decent man and a good broadcaster. ("I don't see this dark thing you seem to see in David Letterman," Wallace’s character says to her husband. "The man has freckles. He used to be a local weatherman. He's witty. So am I.”)
Letterman was the guy from Indiana who became a weatherman then went to L.A. to pursue stand-up comedy, who landed a spot on his idol Johnny Carson's show and then launched out on a show of his own that set to ironically deconstruct the format on which he grew up. William Knoedelseder's book, I'm Dying Up Here, provides good background regarding Letterman's time at The Comedy Store in Los Angeles, highlighting nights when "from opposite sides of the room, two men heckled him simultaneously. [Letterman] fired back, “Are you two guys sharing a brain?” Another night, a drunken Ringo Starr heckled him and Letterman—not knowing it was Ringo, and not particularly caring when he was told—responded back with gusto. Letterman is the man who—per longtime television writer Bill Carter—created a second beachhead of late night success that wasn’t The Tonight Show. He spoke movingly after 9/11. He inspired Jimmy Kimmel, Jon Stewart, Louis C.K., Norm MacDonald, and countless others.
So what does it say about American life, television, comedy, your horoscope, the passionate debate over emojis, kale, and tonight's winning lottery numbers that David Letterman is retiring? Hank Steuver at The Washington Postthinks that the question to ask is to ask if people have “... noticed how, on these [new late night] shows, that it’s not at all about subverting the celebrity culture from within, but just rolling around in it like pigs in A-list mud?” A writer for Conan O’Brien derided the current landscape as something resembling "Prom King Comedy."
But that isn’t the point, and it was never the point: while that writer for Conan was complaining, Letterman was running around the street with Billy Eichner and shouting at New Yorkers. The point is the man, the jokes, and the speed and specificity with which it was all done.