Literature Society: Letterman: The Last Giant of Late Night

I chose the title The Simpsons Decade for my column on post-modern, meta-textual 1990s comedy for Rotten Tomatoes because, in addition to being the greatest TV show of all time, The Simpsons refined and perfected a comic sensibility that would define the Clinton Era. The Simpsons changed television forever but it was building upon the innovations and attitude of Late Night with David Letterman. 

The Simpsons and Late Night with David Letterman shared a number of writers, often egghead recent graduates of The Harvard Lampoon, most notably George Meyer, but they also shared a sensibility at once irreverent, absurdist, deeply satirical and filled with richly merited contempt for hypocrisy and phoniness in all its forms, but particularly of the show-business variety. 

David Letterman helped create the groundwork for The Simpsons and The Simpsons Decade. So did Bill Murray. So did Steve Martin. So did Albert Brooks. So did Andy Kaufman. What all of these icons and visionaries shared was an ironic distance from show-business and show-business conventions that allowed them to simultaneously inhabit, subvert and mock the role of the smarmy, insincere show-business phony. 

Letterman was, and remains, a giant. But decades into one of the most influential and accomplished careers in all of show-business, Letterman remains an enigma. Letterman came into our homes every night for longer than some of his fans have been alive yet he is fundamentally, unknowable in the way we secretly demand our legends to be. 

Letterman’s fundamental unknowability poses a challenge for biographers. How do you plumb the depths of someone so ferociously private? How do you barrel past walls as formidable as the ones Letterman has built over the course of his career? Zinoman’s answer is to explore Letterman almost exclusively through his work, through his shows, through his comedy. This is a biography of a career as much, if not more, than a biography of a man. 

The New York Times’ Zinoman is particularly savvy in chronicling the ways in which Letterman has revealed himself through his work, the way there really does not seem to be any real separation between Letterman the prickly and cantankerous comic genius and beloved performer and Letterman the famously prickly and cantankerous human being. 

Letterman is a true pop culture original, but Zinoman argues persuasively that his comic sensibility was shaped and molded by a series of talented, distinctive collaborators, most notably Merrill Markoe, Letterman’s longtime head writer and girlfriend. Markoe is a hero among comedy people and comedy writers, revered as the woman behind the man, the cult figure behind the household name. 

If Letterman had not fallen under the influence of Markoe, with her bohemian love of ideas and oddball sensibility, Zinoman suggests that his life and career might have traveled down a very different, much more conventional path. Throughout Letterman, a war is waged for Letterman’s comic soul between boundary-pushing innovators like Markoe and Chris Elliott, who were continually pushing for Letterman to experiment with the medium of television, to take it apart and put it back together and blow it up spectacularly, and more conservative, mainstream influences who reflected Letterman’s own Midwestern roots. 

Left to his own devices, Letterman might have developed as nothing more than a younger, quirkier, hipper version of his hero Johnny Carson. Letterman’s early path through show-business was anything but radical. He was a weatherman, a radio personality, a supporting player on Mary Tyler Moore’s short-lived variety show, which I covered for one of the final My World of Flops over at The A.V Club and the host of a morning show that laid the foundation for Letterman’s late-night empire. 

Letterman depicts its subject as explosively, naturally, instinctively funny but in a unique way. Letterman was never an actor, and he wasn’t really a stand-up comedian either, in the traditional sense, but when he hooked up with Markoe, they became infinitely more than the sum of their parts. They were complementary opposites, the lanky, beer-drinking Midwestern wisenheimer, cut off from his feelings and emotions, and the artsy, bohemian intellectual who obsesses about her intense and fascinating emotional life in fascinating diary entries occasionally excerpted here. 

To paraphrase the original title of the Sean Connery/Jon Stewart dramedy Playing by Heart, writing about comedy can be like dancing about architecture. Conventional wisdom holds that nothing ruins comedy like analyzing it, and that reading accounts of comedy can’t possibly compare to the thrill and excitement of actually experiencing it firsthand. Nothing is supposed to kill a joke like explaining it, or trying to explain why it's funny. 

Get a load of this terrifying motherfucker!

As a dude who writes about comedy extensively, I unsurprisingly have a different perspective and in Letterman, Zinoman does a fantastic job of establishing just how surreal and experimental and bold Late Night with David Letterman was at its delirious, almost avant-garde prime. Letterman conveys the visceral excitement that came with every new episode of golden-era Late Night, the sense that anything was possible, and at any moment this whole crazy spectacle could devolve into madness and anarchy. 

For a while, Late Night with David Letterman was at the white-hot epicenter of pop culture, not just comedy, the way The Colbert Report and The Daily Show were in their own respective primes. That kind of heat and furious, constant innovation is impossible to sustain forever, and Letterman chronicles how Letterman both evolved and de-evolved as an artist and as a talk show host, moving steadily away from the trippy, mind-bending conceptual comedy of Late Night’s early years towards a more personal, story-based and personality-driven style reminiscent of early The Tonight Show host Jack Paar.

Then Letterman made the big move to CBS, a bigger studio and an earlier time slot and his already fading appetite for crazy conceptual further faded even as Letterman increasingly revealed new sides of himself. Zinoman does not put too fine a point on this, but one of the tragedies of Letterman’s career is that a man who received so much of his comedy and cultural education from a woman increasingly marginalized women on his own show. 

Towards the end of his run as a talk show host, Late Night employed a stand-up named Eddie Brill as its talent booker who infamously dismissed Amy Schumer as a “comedian’s girlfriend” and also representative of the fundamentally unfunny nature of female comedians. Female guests were often there for the host to ogle and Letterman apparently saw the attractive women on his staff as his own private dating pool/harem. 

Look at how adorable Letterman's son is! A chip off the ol' block.

David Letterman is a hero. David Letterman is an asshole. Letterman does justice to both sides of this complicated man. Late in the book Markoe, who had ended her personal and professional relationship with Letterman because even a woman as fierce and strong-willed as her can only take so much, is offered an opportunity to write filmed bits for Stephanie Birkitt, a spunky assistant who became a big on-camera presence while she was cheating on her boyfriend with her married boss. 

Markoe did not know that Birkett was sleeping with Letterman at the time. The full-on bizarreness and cruelty of the situation would not become apparent until much later. Letterman cheated on Markoe, an employee on his show, with Regina Lasko, another employee, who he went on to marry, just as he would go on to to cheat on Lasko with yet another woman who entered his life while she was an employee of The Late Show in Birkett. 

It’d be a crazy shit show of a situation even if the highest-profile blackmail attempt in television history wasn’t also thrown into the mix when Birkett’s boyfriend threatened to bring Letterman’s indiscretions into the public eye by writing a thinly fictionalized screenplay about Letterman and Birkett’s relationship, only to have Letterman alert the authorities and go public with both the blackmail attempt and his extramarital relationship with multiple staffers, not just Birkett. 

For an intensely private man, it was a surreal situation. Viewers used to knowing nothing about Letterman’s personal life suddenly found themselves knowing, if anything, too much about the sordid situation the late night icon found himself in. Letterman's love life had always been his own damn business. Then it somehow become everybody’s business, including the tabloids and law enforcement. 

Anyone know if these guys are still friends? 

It’s a particularly interesting and fraught moment for Zinoman, who otherwise only seems interested in Letterman’s personal life to the extent that it informs his work. And this was unmistakably a case of Letterman’s private life and career blurring in a way they never had before. 

It was a crisis that reflected the best and worst in Letterman. The TV star could have avoided all of this unpleasantness by not cheating on his wives or girlfriends, and by not availing himself sexually of the much younger women who worked for him. The scandal similarly did nothing to counter Letterman’s growing reputation as a dirty old man, a leering, almost Howard Stern-level voyeur who did little to hide or mask the amorous feelings towards the talk show’s never-ending parade of sexy movie stars and leggy supermodels. Letterman was notorious for looking, but this scandal indicated that he did a whole lot more than gaze lasciviously at women he was attracted to. 

Yet the scandal also highlighted the sometimes brutal honesty and bluntness that has made Letterman a hero to multiple generations of smartasses. Letterman was willing to look sleazy and immoral rather be lured into a murky criminal underworld in an attempt to cover up his sins and indiscretions. 

Letterman had done something deeply dishonorable. He had abused his power and authority to cheat on his wife with multiple women yet he won over much, if not all, of the public by being forthright about his indiscretions even if he was understandably hesitant to reveal the full extent or nature of his sins. 

It’s hard to imagine the man deftly chronicled here not working. Clearly, work made Letterman deeply miserable but it’s just as achingly apparent that not working makes him even more miserable. Letterman’s personality is impossible that way, but it’s that very impossibility that makes him such an elusive and exciting figure. 

So perhaps it’s not surprising that Letterman is returning to comedy through a new project via Netflix. The grey-bearded old lion will be loping back into public view to entertain a public he’s seemingly always felt deeply ambivalent about. For possibly the last time in his career, Letterman will be reinventing himself and his career while hopefully remaining the righteously cranky bastard we’ve come to know and love, and also feel deeply ambivalent about as well. 

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