10. The Best Things in Life are Worth Staying Up For
David Letterman has been at CBS since 1993. Even back in the 90s when the so-called "Late Night Wars" were at their peak, there was a sense that late night TV was a dying enterprise. When Johnny Carson retired, it was clear that he could never be replaced, and not simply because of his talent or personality. The culture was already moving past the idea of three-network dominance, appointment viewing, late-night button-down white guys sitting behind a desk telling jokes. It wasn't just Arsenio Hall, and it wasn't just cable, but those were big parts of it. The idea of a monolithic American culture apparatus (if such a thing ever existed outside of the idea itself) was already splintering, and would not leave the decade intact.
In that sense, at least, David Letterman was a perfect fit for the times. He wasn't Carson, and would never have the ability to reach across demographics the way Carson had done. He was rough, with too many sharp edges, and - fatally - without the ability to reassure his audience that they were always in on the jokes. He was cool in a way that appealed to college kids and city dwellers. He took risks to be funny, and part of those risks was alienating people who weren't willing to meet him halfway.
It's odd to think of it, now - he had a nightly talk show on NBC for over a decade, but the media landscape was such that he could still be considered a cult proposition. Your dad or grandpa turned the TV off when Carson was over, and that was when the kids turned in to Letterman. It wasn't quite like that in my household. My parents were always fairly agnostic on Carson (they are both - from my perspective - remarkably anti-nostalgic in regards to the pop culture of their youths), but they were Late Night fans from very early on, and they passed that on to me. So this was the game: Friday nights, holidays, and Summer vacation, it was time to stay up and watch Letterman. Maybe if I was lucky I could make it through the monologue, the Top Ten list, and the first guest. I figured out how to use the VCR (which wasn't that easy) so that I could record the show when I wanted, when the TV Guide said there was a good musical guest. There's a chance that old VHS tapes containing episodes of Letterman with They Might Be Giants and Richard Thompson as musical guests still remain hidden somewhere in my parents' house.
And this was what the cool kids did in the 1980s. And if that sounds facetious, it wasn't, not at all. Irony had not yet conquered the world, but Letterman was the prophet.
9. It's OK to be the Smartest Guy in the Room
Letterman didn't give a fuck what you thought about him. That, especially, is hard to discern now: it's not like his attitude has appreciably changed, but he's become an elder statesman by default, avuncular and deeply respect and beloved even by the kinds of people who slept through his 80s heyday. But if you go to YouTube and watch any of the old episodes of Late Night archived there, you immediately see the difference.
He was born in Indiana but every bit the New Yorker. He spoke fast and thought faster. He wasn't afraid to filet any guest who dared cross him. Of course that would have rankled people. If you were used to Carson's kind patience with guests of all stripes, from the A-list to 15-minute-famous civilians, the idea that a talk-show host might bite back must have seemed not simply strange, but utterly mean-spirited.
But the rules were simple: if you came to play, Dave was more than happy to play. If you weren't on board with that, you might be in trouble. Tony Randall was one of Letterman's greatest guests, and not just because he happened to live in the neighborhood and could always be counted on to fill-in for a last-minute cancellation. Randall liked to play, and Dave liked having someone on board with whom he could spar for fifteen minutes. It was unpredictable and sometimes disastrous, but when it worked it was sublime. Guests who would have been completely DOA on another format - folks like Andy Kaufman, Harvey Pekar, and Crispin Glover - were welcome to be as cranky or unpleasant as they could be, because the understanding was that a disastrous interview was more memorable and enjoyable than a mediocre chat. Even late into his CBS run he was able to conjure up magical moments like Joaquin Phoenix's dada interview, humiliating on the face of it but riveting for the obvious relish Letterman still enjoyed at being able to sharpen his wit against a moving target - who had, regardless of his motivations, obviously come to play.
He nourished long-term public feuds with the likes of Cher because it was funny, and the rough-edges were part of the appeal. If Letterman hadn't existed, it would have been necessary for Madonna to invent him - the perfect rascally foil, unwilling to play the same old celebrity game with someone so obviously adept at playing that game to their own advantage. His later attempts to manufacture a spat with Oprah, while less engaging, were still funny because they proved he was still adept at leveraging other celebrities' supposed strengths into surprising vulnerabilities. For Letterman, there was and remains nothing more absurd than the idea of being a celebrity, and if you didn't get that, you weren't going to get on well with Dave.
8. It's OK to be a Smartass
Letterman is an intelligent man and the impatience with which he sometimes confronted his guests was matched by the impatience he approached much of the rest of the world. The banality of stupidity has always been one of the major motors of his comedy. That's one reason why even his most absurd bits carried a bite. The world is a pretty silly place, and sometimes the only rational response to this kind of silliness is to become silly yourself.
This is the worldview of the smartass, the guy cracking wise in the back of the classroom because his mind is working twice as fast as everyone around him and he just can't be bothered to slow down or pretend not to care. It's a form of cynicism, sure. But cynicism has a bad rap. No one wants to be called a cynic, but there's nothing dishonorable in holding fast to the belief that humans are often motivated by greed, ignorance, or self-regard. That observation is central to most forms of comedy, certainly most memorable comedy, from Aristophanes through to Richard Pryor. So while Letterman has often been criticized for being a prime contributor to the rise of irony in the 90s, and the corollary culture of cynicism pilloried by conservative and centrist ideologues for the past few decades, any critique that focuses on the negative effects of cynicism ignores the root cause of such cynicism - that is, the deep gulf between ideal and reality, and the corrosive effect of hypocrisy. Don't blame Letterman for ushering in an age of ironic disconnection (as per David Foster Wallace), blame the age which mandated the use of irony as a necessary survival mechanism.
7. Tradition is Important, Except When it Isn't
As much of an iconoclast as Letterman has always been, he is also a sincere traditionalist. He was Johnny Carson's anointed heir, after all. For over thirty years he used his shows as a venue to introduce new talent, both comedic and musical, in much the same way as Carson had done for him. He deeply respected longtime broadcast fixtures like Regis Philbin and Jack Hanna. He never missed an opportunity to spotlight older comedians who had influenced him. He loved nothing more than spotlighting older artists who had perhaps been left behind, figures such as Warren Zevon and Darlene Love. Even though he was an Indiana Presbyterian, he maintained a vital connection to the tradition of New York Jewish comedians of the kind who rose to prominence in Vaudeville and the resorts of the Borscht Belt. He was careful with those jokes, because they were antiques.
But his respect for these traditions was matched by his willingness to warp and break convention when necessary. Although he worshiped at the alter of Carson, his show was largely defined by the conscious attempt to break away from Carson's mold, a necessity bred by the network's insistence that Letterman avoid simply replicating Carson's formula an hour later. Late Night, especially in the early years, was defined by an enthusiastic desire to break from formula, to take conceptual risks, to potentially alienate anyone who wandered in simply because they didn't feel like turning off the television after the credits rolled on The Tonight Show.
6. Humility First, Last and Everything in Between
Letterman has never been shy about broadcasting his anxieties and insecurities regarding his own abilities. He's a notorious grump, a tendency born from an oft-repeated conviction of his own shortcomings.
With this in mind, Letterman's most endearing trait is his willingness to lean into his own imperfections. He gets a lot of mileage out of his face, not conventionally handsome by any standard, gap-toothed and curly haired, a face made for radio if ever there was. Gaffes and bloopers, both his and others, became one of the show's most enduring preoccupations. Even after he had moved to CBS and the show became a much slicker, far less (intentionally) ramshackle affair, he still maintained a looseness that belied the slick craftsmanship required to produce a nightly talk show. This was a stroke of genius, as it allowed him the freedom to embrace accidents when they occurred. Even through to the very end, Letterman maintained an air of wry dissatisfaction, a faux-ironic exasperation that you might associate with a man who long ago made peace with his status as an imperfect creature in an imperfect universe - "trapped in a world he never made."
5. Living Well is the Best Revenge
The Late Night Wars seem in retrospect like the silliest pop culture phenomena conceivable. Two larger-than-life TV comedians fought a brutal dynastic struggle over possession of The Tonight Show. NBC gave the spot to Jay Leno, despite Letterman's success in the 12:30 AM spot, and regardless of Carson's own probable preferences.
As awful as it might have seemed, NBC made the logical choice. Letterman wasn't quite ready for prime time, certainly not in a way that would ensure a smooth continuity between Carson's tenure and that of his successor. Jay Leno was at one point a very funny man, highly respected by his fellow comedians. But when he accepted the job as Carson's replacement the understanding was that he would continue to steer the ship with the same kind of centrist mass appeal that had made Carson such a beloved figure. And he did. Sometimes he was even still funny.
The problems for Leno were twofold. The first obstacle was that, despite his success as a host and brand caretaker, he accepted the job as a kind of poisoned chalice. For most of his tenure he maintained a respectable lead on Letterman, capturing the larger part of the mythical "middle American" viewer who simply disliked Letterman on principle. But for critics and fans of comedy, he was forever branded, uncool at best and a betrayer at worst. He may have been consistently more popular than Letterman, but he could never close the "cool" gap.
The second problem was a media landscape teetering on the brink of seismic change. The age of monolithic consensus figures in American broadcasting was coming to a close. Johnny didn't need to be "cool" and he never suffered from being "uncool" - he simply was, in the same manner as Walter Cronkite. (I'd argue that the closest we still have to such a figure, oddly, is Alex Trebek - his eventual departure from Jeopardy will represent almost as significant a shift as Letterman's goodbye.) But suddenly there were choices, and in a world of choices the very idea of centralized media landmarks became laughable. Jay Leno was no Johnny Carson. The culture no longer needed Johnny Carson.
Fast forward to 2010. Regardless of his success, Leno's broadcast career shuddered to a close in the most dismal manner possible. Despite a well-intentioned attempt to avoid the same rancor that had marked Leno's ascension to the post, his retirement from The Tonight Show proved even more contentious than Carson's. Leno publicly named Conan O'Brien as his successor. He left amicably and O'Brien took over. The problem was that O'Brien was even more of a niche figure than Letterman had been, and ratings fell accordingly. NBC tried to stem the bleeding by giving Leno a new slot at 10:00 PM, essentially an opportunity to do The Tonight Show an hour earlier, to appease affiliates desperate for a stronger local news lead-in. The attempt failed. O'Brien was fired. Leno returned to The Tonight Show for another four years, before retiring again in 2014, his reputation obliterated.
Because Letterman was widely perceived as having been betrayed by NBC in 1992, he had the moral high ground throughout the decades of his competition with Leno. He grew in stature while Leno shrank. He leaves The Late Show universally adored and respected, a towering figure in American broadcasting history. Leno leaves no legacy, save as a cautionary tale.
4. Don't be a Creeper
Unfortunately, Letterman fell victim to his own vices. If he had more professional integrity than Leno, he occasionally overstepped the bounds of personal propriety. He has an uncomfortable history in regards to his treatment of attractive female guests. Sometimes it was all fun and games, and sometimes he veered into shady territory - as a respected male authority figure, sitting across the desk from some of Hollywood's most attractive starlets, crossing boundaries in a manner that seems more regrettable with every passing year.
Of course, some of his strongest bonds were forged with female guests with whom he shared a sincere affection, and even attraction - stalwart friends such as Teri Garr, Julia Roberts, and even Blake Lively. But sometimes his randy old man schtick became too much, and because of his authority the behavior passed mostly unremarked.
3. When You Do Wrong, Fess Up
It seems perverse to praise a man simply for apologizing when caught in the act of wrongdoing, but that's the world we live in. Considering the degree to which almost every celebrity or political scandal is met with evasion, obfuscation, lies, or legal action, the spectacle of a famous man - one of the most famous men - stepping in front of the scandal and admitting his mistakes in the most candid manner possible was remarkable. It remains remarkable. What should be regarded as the rock bottom of human decency - the willingness to admit wrongdoing and meaningfully apologize - is so rare that Letterman's principled admission immediately became the gold standard for public accountability and integrity. It could even be argued that the novelty of his admission deflected a great deal of legitimate criticism that might otherwise have further corroded his public image.
But whatever else can be said about him, Letterman abhors hypocrisy. He couldn't stand the idea of being a hypocrite himself, so much so that when cornered by the evidence of his own malfeasance he faced the consequences as boldly as possible. He hurt a lot of people and acted terribly, but rather than compounding the problem by prolonging the conflict he simply admitted his liability and expressed his contrition. It's not our responsibility to forgive him, but his actions in the years since the scandal reveal a chastened man, deeply dedicated to his family and conscious of the ways in which his abusive behavior nearly cost him everything. Better men have lost their careers for less, but his unexpected apology saved him. He'll always have that asterisk on his legacy, but it will be paired with another enduring lesson: the virtue of a man lies not in perfection, but his confrontation with imperfection.
2. Even Pioneers are Forgotten
Last week I was having a drink with friends and mentioned that, since learning that Letterman was leaving, I had set a recording on my DVR and was watching every show leading up to the finale. The folks I was out with were just a few years younger than me - but just a few years was enough. No one at the table understood why Letterman was a big deal, had been one of the most influential personalities in the history of TV. Wasn't he just another old white guy behind a desk?
Of course, in the heat of the moment you can never find the words to marshal the perfect rebuttal. I stuttered out something bland about being "influential." Nothing particularly convincing. But in that instant it clicked for me that in order to understand why David Letterman was important, you needed to have been alive and paying attention during a surprisingly narrow window of time. Letterman made his name in the 1980s, and although he's been consistent and consistently good for most of his career since, the reason people who know speak with such reverence is that they remember when there was nothing at all like him on the television. Now, everybody is like him, in some way or another. No one with an ounce of conviction wants to be Jay Leno.
His medium was transient. He never had a string of best-selling comedy records that new generations can rediscover for years to come. He never did movies. He hasn't done stand-up in decades. The innovations he introduced over the course of many years have been so subsumed into the television landscape that simply just explaining that he was the first to do or say or be something or other isn't enough - there's no existing context for how strange it was, at the time, to put a TV camera on the back of a monkey, or get into shouting matches with belligerent guests, or pay a weird old man with coke-bottle glasses to stand there and scream at the camera. There was no such thing as viral video back then, so if you saw something truly special on Late Night the best you could do was hope to pick it up on summer reruns, or find a friend who just happened to have been recording the show on their VCR. Because that's something we did back then.
But that's OK. Even if talk shows are the most ephemeral of all television programs he'll be remembered for a while to come, even if the specifics of his career and influence eventually fade. For historians and scholars, he'll remain important. The people who were inspired by him will, in turn, inspire others, and so on for the foreseeable future. Those of us who remember his prime will cherish the memories for as long as we're around, but our children will cherish other memories, and that's OK, too.
1. The Only Safe Target is Yourself
It's been remarked so often that it threatens to become a cliche: comedians should always punch up, never down. Letterman, in his decades-long crusade against hypocrisy, did a good job of observing this rule. Sure, there were jokes at the expense of small-town yokels and clueless tourists, the usual late-night fare. But he always reserved the larger part of his scorn for politicians, corporations, ignorant celebrities, and other men and women of influence. If you were famous, if you took yourself too seriously, you were fair game.
But the biggest target was always himself. His insecurity, his anxiety, his goofy looks, his shortcomings as a comedian and a host, his moral and ethical lapses - the cruelest wounds were self-inflicted. And this is vital, if you appreciate Letterman for no other reason, you must remember that as scathing and cynical as he could be, he was never more critical of anything or anyone than of himself. That imprinted on me at a very young age. You can't be critical of others if you can't be critical of yourself. Honesty in regards to your own faults is disarming. Self-critique can also become a means of protection. If you broadcast your faults with honesty, you're cutting your critics off at the knees.
Making fun of yourself is endearing because so few people do it effectively, and it can also make people uncomfortable when wielded strategically. Maintaining control of a situation while acknowledging the element of unpredictability is one of the most valuable skills a person can have. Loyalty matters. Acknowledge your elders before rejecting them. Make time to thank everyone. Enjoy every sandwich.