David Letterman didn’t walk a fine line, he built his show right on top of it.

For an 80s kid with aspirations of working in broadcasting, Late Night with David Letterman was a fascinating mix of sarcasm, sincerity, irony and snark, sometimes all at the same time.

David Letterman stepped down after 30+ years on television this week. Another fawning treatise lionizing him for his brilliance isn’t really necessary, but nevertheless I wanted to write about his impact in an abstract sense. As a kid growing up in the 1980s with a penchant for the weird and surreal, and who harbored ambition to go into broadcasting, Late Night with David Letterman was must-watch TV.

Countless epilogues have been written, lauding his impact on television, or decrying him for “making the world a meaner place“. Is he the most engaging television personality in history? No. Is he, as Cher famously referred to him, an “asshole”? Maybe, but nor is he a corrosive influence on society. What Late Night represented, to me anyway, was a unique and difficult to describe boundary-pushing niche. After he moved to CBS, and got older, he captained a more conventional ship, in a sense like his idol, Johnny Carson. But his downright bizarre morning show, and subsequent NBC incarnation of Late Night, brought the experimental and absurd to the straight-laced network television universe.

Watching Late Night with an eye for the craft of making a show was a revelation. The show was a sort of quantum particle tenuously flipping state between sarcasm, sincerity, irony and snark, and this was groundbreaking, because it hadn’t been clear there was a place amidst those competing concepts to occupy in the first place. The early 1980s was a world where television viewers got used to being served up neat little narrative packages, with pretty bows on top, and then here came a gift that not only was shabbily wrapped, but you weren’t even sure what it was, and it often didn’t make any sense.

A particularly famous recurring bit was the Top Ten List. In its later years, the bit was essentially a grouping of jokes about politics or pop culture, but when it started, the whole point of the Top Ten List was that it didn’t make any sense. “Top Ten Pharaohs or Tile Caulkings” is one example. After a while the writers apparently had become tired with the bit. Perhaps boredom led them to come up with “Top Ten Reasons To Continue The Top Ten Lists Just A Little Longer”, comprised of a bunch of non-sequiturs. He follows the list with “viewer mail”, another recurring bit, which on this night serves instead as a vehicle to mock comedy itself. As people would say now, this is an example of when the show gets “meta”, and Late Night ventured into this sort of territory with regularity.

There are notorious stories of Letterman’s perfectionist nature, about how he would blow through two or three dozen jokes in the afternoon before selecting the four or five for the purposefully hokey monologue at the top of the show, or review the show after taping and rip it apart with a self-critical eye. So, they worked very hard to create a monologue that was essentially subverting the idea of what a monologue was, and went further, mocking the entire talk show format, even as Late Night deftly stayed within its boundaries.

This is why the most brilliant moments of Late Night with David Letterman in the 1980s were when the show veered into intentionally oblique territory. To put it in Letterman’s words from an excellent recounting of jokes that didn’t make the show:

I love the idea that the audience doesn’t know for a while whether it’s a joke or not.

And then there were the interviews, which sometimes also seemed to to be jokes…or not. Some of them inhabited this space that one wasn’t sure was friendly, or combative, or mocking, or just pure snark. Consider the various appearances of Harvey Pekar, a curmudgeonly comic book artist from Cleveland:

You look at this and you think “what exactly is going on here?” Perusing the comments on YouTube is amusing, because people take different things from it. (Pekar’s a loose cannon, Letterman’s an asshole, Letterman’s a corporate shill, Letterman was trying to be nice, whatever.) It is clear that in this interview, Harvey Pekar is being himself: an antagonist to power, while Letterman plays the role of member of the establishment, but I think it’s more complex than that.

These sorts of guests (Andy Kaufman was another) were Letterman’s way of subverting the ass-kissing, movie-plugging format. He’s the guy in the suit, he’s the straight man, and Pekar gets the latitude to rant. He appears to be sincerely annoyed with Pekar, telling him this forum isn’t appropriate, and is dismissive of his work creating comics (while at the same time giving the regional artist national exposure).

The obvious question is: “who chooses the guests?” The answer, of course, was Letterman. It was his show, and he decided who was on it. Letterman knows what Pekar represents (a man who holds no regard for the status quo, and who will not abide by the rules of talk show decorum), and though Letterman seems to have little respect for him, you see that after the contentious exchange, and a commercial break, Pekar’s still there, and the two men shake hands as the end music plays.

It was seat-of-the-pants TV. Letterman didn’t mind just throwing stuff out there (or off a five story tower) to see what happens, and these experiments frequently failed. But it didn’t matter, because he seemed to revel in awkwardness and uncomfortable silences as much as he reveled in laughs (often his own). He endorsed the absurd with repeat guests like Kaufman and Pekar, but also Penn & Teller, Jake Johannsen, Emo Phillips, Super Dave Osborne, and many more. One could argue that Late Night helped create space for absurdists who followed into the 1990s with vehicles like Ren & Stimpy, Mr. Show, Adult Swim, Kids in the Hall, Space Ghost Coast to Coast, and others. This is a very unique, and amusing, legacy to have, and it’s as difficult to pin down as Late Night was difficult to describe.

In 1986 a particular episode featuring Raquel Welch was rerun while they were on break. It was aired in its entirety, but dubbed – in English – with different voices (Dave and Raquel voiced by Peter Fernandez and Corrine Orr, from Speed Racer). No explanation was given. 250 people called NBC to complain about the “error”. That pretty much sums up what Late Night with David Letterman was.

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