The papers have been signed. When David Letterman tosses his final Top 10 List card into the audience at the Ed Sullivan Theater on May 20, Stephen Colbert will be the one to take over "The Late Show" on CBS. This, of course, is no longer news. Yet only recently have I begun to realize what exactly this turnover might mean. See, I’ve been thinking a lot over the last year or two about what “funny” is. The result of humor—the cherished laugh—is easy enough to identify, but it is far more difficult to put your finger on what actually makes us laugh. So when I recently visited my mother in the home where basic cable never dies, and I reunited with David Letterman for the first time in years, I found it not just enjoyable or surprising but interesting that I still find Letterman funny. Later that night, with my feet hanging off the end of my childhood bed, and my mother’s TV so loud that the small hours infomercials would work their way through the wall and into my dreams, I realized that maybe what makes us laugh is not as much about what a comic says as it is about what his or her audience needs to hear.

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Perhaps the best way to identify what is special about Letterman is to compare him, yet again, to his late night ratings rival from over the decades, Jay Leno. Though Leno retired from late night television early in February of 2014, during his roughly 22 years on the air Leno’s ratings almost always remained higher than Letterman’s. And yet I’d speculate that Letterman fans, though smaller in number, were the more rabid and faithful bunch, the sort that, back in that pre-TiVo era, canceled previously scheduled social engagements in order to gather around the television and check in with Dave. But why, then, were Leno’s ratings better?

I’d posit that Leno and Letterman represent two stark takes on what “funny” is. The difference is far greater than the varying ways in which both comedians (and they did both get their starts in stand-up comedy) are so often rendered cartoonish: a chin like a ski-jump; a smile that, as they used to say of Eleanor Roosevelt, could bite an apple through a picket fence. No, the most important, though perhaps least obvious, difference between Leno and Letterman’s two approaches to the late night television variety show is the way each host appeals to his particular audience in his own way. The significance of this difference is rooted in something we often take for granted: why we watch the shows we watch. Leno and Letterman’s respective audiences tune in not only for the jokes that send them off to sleep but for what they get out of those jokes, something intangible, but something that also might help them sleep more soundly.

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I have to admit that I’m not a Leno guy. I’ve seen his stand-up from early in his career, and he was good. He was what I consider “funny.” In fact, even today his stand-up, which he often performs at the Comedy and Magic Club in Hermosa Beach, California, can be insightful and cutting. But his performances as the "Tonight Show" host always struck me as safe, formulaic and predictable. By the time he had finished setting up his joke, I had already anticipated the punch line.

A recent study done by George Mason University found, in an analysis of Leno’s more than 4,600 shows and 43,892 jokes, that Leno’s most frequent target was Bill Clinton (4,607 jokes). Honorable mentions go to George W. Bush, the runner-up (3,239 jokes), and O.J. Simpson, the highest-ranking celebrity (795 jokes). However, for reasons that will soon become clear, to illustrate Leno’s predictability I’d like to examine a classic example from 1994, the year that granted late night television the gift of Tonya Harding (only 49 jokes). Here is the joke, taken from an opening monologue: “Tonya Harding is going to be naked in Penthouse next month. Well, I guess her agent says she may sue Penthouse for publishing nude photos of her. I guess they’re nude photos of her and [her ex-husband] Jeff Gillooly having sex. Now, Tonya says that sex is a private matter between a woman...and the guys in her trailer park.”

To be fair, few jokes are as funny on paper as they are live. But still. This joke’s humor hinges in the last line’s pause, which marks the turn in the joke. Prior to the turn, the setup prepares us for a familiar phrase: between a woman and a man. Almost every joke’s setup is written to set up the listener’s expectations, then the punch line subverts those expectations. The subversion is where the laugh comes from, that moment of surprising inevitability. However, Leno’s jokes often set up our expectations, then “subvert” them by meeting another, second familiar set of expectations: instead of completing the phrase “woman and man,” he calls Tonya Harding trailer park trash. Tonya Harding was “famous” by now for being “trailer park trash.” A Slate article written in early 2014, after two documentaries were released that explored Harding’s difficult life after the scandal, describes Harding like this: “Harding was the trailer trash, even before the knee-capping: She grew up poor in Oregon in an unstable family (though never, as she tells NBC, in a trailer park).” She had to explicitly state in an interview with NBC that she wasn’t from a trailer park, because her reputation preceded her. Leno may be subverting the expectations of his own joke’s setup, but he rarely subverts the expectations of his viewers.

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E.B. White thought that “Explaining a joke is like dissecting a frog. You understand it better but the frog dies in the process.” My purpose here is neither to needlessly murder jokes nor merely criticize Leno, but to understand the late night legend’s appeal. The first step is to isolate the way his jokes simultaneously subvert one set of expectations while fulfilling another as the defining trait of his humor, the quality, it would seem, that drew so many viewers to "The Tonight Show" for more than two decades. Let us call this trait “predictability.”

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In the end, we turn to all comedy for catharsis. So the question becomes: catharsis for or from what? To answer this, with regard to Leno’s comedy, we have to reconcile the predictability of his jokes with the fact of his high ratings. What do people enjoy about such predictability? What do they get out of it? It strikes me that Leno’s tendency to structure jokes that subvert the expectation of their setup by relying on familiar preconceived notions about a topic for the punch line grants his audience the ability to foresee the other shoe in a joke before it drops; it offers a moment when the voice in your head provides the punch line and you have a private laugh before Leno finishes the joke and everyone gets to share in laughter together. This dynamic gives the viewer catharsis in the most basic form of expectations being met.

As I see things, Leno’s predictable jokes appeal to a wide variety of viewers, which in itself might help explain his popularity. Many of Leno’s viewers—perhaps even the majority— might find enjoyment in his jokes because, being on the periphery of popular culture, the jokes actually do surprise them. Another group might seek from television in general, not just comedy, entertainment that does not challenge them to think, but serves more or less as white noise, a source of mindless relaxation. But there is another group of Leno viewers, and these viewers hold for me a particular interest. This group is composed of those who are familiar with popular culture and who are able to anticipate most every joke’s payoff. My suspicion is that these viewers might enjoy the reinforcement that their pre-knowledge grants to their sense of their own intelligence. In its own way, after all, any joke structured in the classical setup/punch line model can be taken as a pop quiz of sorts. The setup poses a question. A breath later, the punch line provides the answer. The interval is a test of your abilities. Did you predict the punch line? In the case of Leno’s jokes, likely you did. Or at least could have. What strikes me as particularly compelling about such predictability is that the setup’s question is all but simultaneously served with its accompanying answer: It causes us to test our intelligence at the precise moment it also affirms our intelligence for us. In short, the viewer is made to feel clever.

Earlier, I suggested we watch the shows we watch because, whether we know it or not, we get something out of them. While it may be easy to explain away fandom of either Leno or Letterman by saying, "He makes me laugh," that is a copout. I want to ask, "Why does he make me laugh?" Here I’d suggest that part of what drew Leno fans from across decades to their televisions each night at 11:35, when most likely they should have been trying to fall asleep, is this pleasure, however deeply buried in their subconscious, of being made to feel clever. After all, if we flip the coin that is pleasure, we often find an anxiety: pleasure as the catharsis of having your concerns quite literally put to bed. Not all anxieties need be outwardly noticeable, all hand-wringing or sweaty palms. Anxieties need not even be conscious. But having our intellect affirmed by every joke’s punch line is a safe way of getting answers to those embarrassing questions about which so many of us quietly wonder, perhaps especially those who seem so utterly cocksure of themselves, since they have banked their identities on the assumption of their superiority: Am I smart? they might ask themselves, somewhere deep in their minds, because to ask others would be to give a reason for doubt. No, but really? Be honest with me.

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If this sounds like a stretch, I’d ask you to consider what happened when cable news was introduced to television. Network news had always had a broad audience to appeal to—one possessing as many demographics as our nation—so they reported stories fairly objectively and left the viewers to make of the facts what they would. But when Fox News and MSNBC emerged, reporting the conservative news and the liberal news, respectively, viewers abandoned network news shows and flocked to the cable news stations that aligned with their political leanings. Rather than confront news that might challenge their understanding of the world, they choose overwhelmingly to watch reporting that confirms for them what they already believe.

I’d suggest that Leno’s show thrived, in part, for a similar reason. And unlike the news, for which primetime is the six o’clock hour, Leno’s predictable jokes provide their affirmation— the apparent answers to those unvoiced doubts—in the hour before bed, that anxious, lights-out alone time in which such useless, pernicious, nocturnal questions come out to play.

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Part of Letterman’s charm, on the other hand, is that he so often leaves his audience baffled.

Anyone who has tuned in for even an occasional episode over the years can attest to the fact that his jokes are as likely to fall on their non-sequitur faces as they are to make you fall over laughing. He takes risks with his jokes, which makes them anything but predictable.

To illustrate, here is a Top Ten List from an episode dated Feb. 2, 1994, in which Letterman tackles Tonya Harding’s ex-husband’s unusual surname:

Top Ten Ways to Mispronounce Jeff Gillooly

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10. Jeff Giloony

9. Jeff Gluey

8. Jif Gellahee

7. Jeff Goldblum

6. Gilly Ooly Ooly Gilly Goo

5. Prisoner #3275

4. Mr. Magooly

3. Chef Boyardee

2. Boutros Boutros Gillooly

1. Guilty

From the outset, it is clear that Letterman is taking a less obvious angle on his target: shooting for Gillooly rather than Harding. But that is nowhere near the only variance between Letterman’s and Leno’s approaches. Much of the humor in Letterman’s list can be attributed to absurdity. More on that soon. For now, just say the name aloud: Gillooly. There is so much to work with. The silly sound of the name is at least equally important as the buildup to the climax of the joke: “1. Guilty.” The first nine jokes prepare us to expect a ridiculous-sounding name at the climax, one that is likely to riff on the name of another figure from pop culture. But the climactic joke hits us instead with a deadpanned, straightforward, no-nonsense one-word punch line. In other words, while Leno gives the appearance of subverting our expectations, by actually meeting another safe set of expectations, Letterman provides genuine subversion.

Now, back to the absurdity. The above Top 10 List was only the first in a series of Gillooly jokes that would run the full arc of the winter Olympics. Gillooly’s name made an appearance on Top 10 Lists again on Feb. 7, 10, 15, 16, 17 and 21 before Letterman ran with the following Top 10 List entry on Feb. 24: “Top 10 Signs You’re Tired of the Olympics – 1. No longer laugh at the name Gillooly.” Here Letterman demonstrates his self-awareness as well as his ability to make a joke at his own expense, while also winking at those nightly viewers, the Letterman loyals. What makes Letterman particularly unique among his peers, however, is that after he admits in one Top 10 List that “Gillooly” has had the humor wrung out of it, he continues to use the name again in Top 10 Lists on March 2 and 3. Absurdity comes in many forms, and one such form is certainly pushing a joke not only past its apex, but past its nadir as well, to a point so far past funny that its very unfunniness becomes funny once more. Call it the absurd resurrection. Of course, this approach risks alienating viewers, many of whom might not think the joke ever reaches the point of resurrection, in which case they’re watching as the nightly beating of a dead horse is nationally televised. Worse yet, the viewers might not have tuned in with enough regularity to recognize the reduction of this joke to the absurd, and so they see only inexplicable randomness and non sequiturs. But for some viewers, the Letterman loyals, moments like this are why they watch to begin with.

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Why do we watch television at 11:35 at night anyhow? The simplest explanation is that we tune in to wind down. Perhaps the kids have finally been put to sleep, the dinner mess cleaned. Or maybe the last-second assignment your boss told you she needs first thing in the morning has finally been completed. We watch to put the day of work and worries behind us, to be led, one laugh at a time, toward a mind still and content enough to fall asleep. So we’re left asking the same question of Letterman that we did of Leno: What do his tired end-of-a-long-day viewers like about his absurd, sometimes even nonsensical-seeming jokes?

When one of Letterman’s viewers tunes in, he or she has no idea what Letterman might say or do. This quality draws a very different viewer than that of Leno’s predictable jokes. By demanding that his viewers tune in nightly for long swatches of time—the entirety of the 1994 Winter Olympics, for example—in order to fully appreciate his jokes, he has certainly sacrificed ratings, but he has also offered his most loyal viewers something unique in late night television, something vital in that near-midnight hour, something even sweet. He offers these loyal viewers companionship. Unlike Leno, whose jokes grant his viewers insider status only for as long as the pause at the turn, between the setup and the punch line, Letterman has structured both his show and his jokes such that they reward the faithful viewer’s long-term dedication. To the casual, occasional viewer, some of the Gillooly jokes likely made no sense. Letterman knows this, and it is OK with him that these viewers might change the channel, because those same jokes will make his loyal viewers feel like insiders; or, put another way, those same jokes make his loyal viewers feel like a part of something bigger than their own small lives. In bed, with the covers pulled up to their chests, another day of trials awaiting them in the morning, with the remote beside them, perhaps where the person they once loved should be, perhaps in the crease of the blankets between them and the husband or wife who is also too tired and stressed to be good company this late in the day, these people are made to feel less alone. They get it.

Leno’s jokes, like his personality, are not crafted to offer this sort of companionship. The jokes are rapid-fire, a humor of succession rather than recursion. As a result, the brief insider’s status offered at the turn of Leno’s jokes—that moment that provides his viewers affirmation, as opposed to Letterman’s companionship—rewards his viewers in an instant gratification sort of way. Somehow, this commerce-like joke transaction Leno has with his audience does not surprise me. Leno presents himself as Los Angeles through and through. He has a sheen about him, as though he has been unpackaged moments before he is pushed onstage. His hairline gives the impression of immortality, and the most widely known fact about Leno, the man, is that he is an avid car collector. In addition to the lack of long-term repetition of jokes in his show, Leno has never revealed himself as human enough to offer his viewers any real companionship. Leno might offer his viewers the comfort of fulfilling their needs for affirmation by meeting their predictable expectations, but I cannot imagine Leno speaking openly about his health issues on his show, the way Letterman did after heart surgery. Nor can I imagine Leno speaking about the difficulties of becoming a father late in life, or addressing his own ugly sexual scandal, rife as it was with blackmail, infidelity and the abuse of his power with female staffers on the show.

Rather, the closest Jay Leno ever came to opening up in a human way was during the controversy he began by leaving "The Tonight Show" in September 2009 to begin "The Jay Leno Show," which also aired on NBC, though at the prime-time 10 o’clock slot. This move was a failure. Fair or unfair, a media-soaked controversy ensued when the network gave Leno his old show back, and removed Conan O’Brien, who had long dreamed of hosting "The Tonight Show." Leno finally addressed the controversy head-on in his Jan. 18, 2010, episode of "The Jay Leno Show." Certainly, part of the thinking here was damage control for Leno’s public image before he returned to "The Tonight Show," but he took almost four and a half minutes of airtime to explain to his viewers that O’Brien’s agents and the cutthroat nature of show business in general had been the real source of this ugly Hollywood pseudo-scandal. Not him. Leno claimed he held no “animosity” toward O’Brien and urged his viewers, “Don’t blame Conan.” This was a rare character-breaking moment for Leno, who almost never spoke on-air of his life beyond Burbank Studios. Unfortunately for him, the humanity he chose to reveal at this moment was at worst a self-serving, conniving sort, and at best further proof that he was completely out of touch. After all, as Lettermen retorted on his show the following night, “No one is blaming Conan.”

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Leno was on late night TV so long it is hard to imagine him as anything other than the character he portrayed nightly. Onstage, Leno was always confident, the king of potshots, all chuckles and chin-jutting smugness. But offstage Leno is by many reports a terribly anxious person. In a Jan. 6, 2013, interview with Oprah Winfrey, Letterman himself speaks to Leno’s “insecurity.” Letterman says Leno is “The funniest guy I’ve ever known. Just flat out. If you go to see him do his night club act, just the funniest.... Therefore, the fact that he is also maybe the most insecure person I have ever known, I could never reconcile that.” Letterman goes on to say, “This is the guy that is documented as hiding in a closet while they were having a business meeting at NBC to decide who would get the 'Tonight Show' chair.” This depiction of Leno is in stark contrast to his onstage persona, and I’d suggest that some of his viewers might even be a bit like Leno: performers in their own day-to-day lives, people who, when confronted by the quiet, inward-looking nighttime hours, are left exhausted by their day’s worth of acting and remain anxious about the reviews. Furthermore, the fact that Leno’s stand-up performances are much more cutting—much more subversive—than his "Tonight Show" performances suggests that he has cultivated this late night, onstage character with his particular audience in mind.

All of this helps explain Leno’s more superficial relationship with his viewers, and why his viewers might find his instant-gratification form of affirming humor appealing. But we can still learn much by examining Letterman’s audience as an opposite of Leno’s in these regards. For example, while Leno’s fans seem to have gotten pleasure from having their pre-knowledge, and perhaps thus their perceptions of their own intellect, confirmed by Leno’s jokes, if we extend the above logic, Letterman’s viewers get pleasure from jokes that could quite easily cast doubt on their notions of their own intelligence. To enjoy a genuine subversion of your expectations, you cannot go into a joke guarded, needing from it one specific punch line. Letterman’s viewers have to be open to their preconceived notions being upended. They have to present themselves as willing to be wrong; in this way, they must enter their viewing experience with vulnerability.

I’d argue it is no coincidence that to have a real relationship with someone, to have companionship rather than merely one-sided affirmation, both parties must be willing to be vulnerable in front of each other. You both might end up looking a fool now and then, but when you know you’re in it for the long run, those moments can even bring you closer together. Even while they’re happening, you’re thinking of the story you’ll have to tell five, 10 years down the road. Remember that time when Dave ... People say such things about Letterman. I have said such things about Letterman. But why do I feel compelled to say these things?

We live in a world that manages to be both permanently connected and increasingly lonely. Sherry Turkle, the cultural analyst and author of "Alone Together: Why We Expect More From Technology and Less From Each Other," has written about this precise trend of our gathering in groups only to get lost in our own private screen-worlds: smartphones, tablets, laptops, TVs. She is by no means the first or only one to make this observation. At least as far back as 1978, Jerry Mander (yes, that is his real name) criticized television for having this isolating effect in "Four Argument for the Elimination of Television." Now, in an era of increased divorce rates paired with lower rates for marriage and an older average age for marriage, Turkle describes our relationship with our devices as compounding the problem of our loneliness by making us feel alone even when we are with others. Interestingly, in the face of this modern predicament, Letterman’s show offers a remedy to the ailment—Is anyone there?—the very screen on which you watch him might cause you.

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I know, I know: Who cares? It’s a fair question, because soon Leno and Letterman will both be retired. Leno has already turned "The Tonight Show" over to Jimmy Fallon, leaving me to wonder, as I watch Fallon’s unflinching grin and schoolboy antics, if the audience’s concerns with their own intelligence might not have vanished entirely, and not due to any universal surge in undoubting confidence, but indifference. Fallon, to me, suggests a more generalized anxiety— Do people like me?—to which unrelenting affability might be a cathartic, if still hollow, cure. As for Fallon’s ability to offer companionship, his eagerness to please belies a human companionship based in mutual vulnerability; rather, I suspect his version of companionship would be like that of a faithful dog, so desperate to make you happy you occasionally want to put it out of its misery. Certainly, I can’t imagine Jimmy Fallon ever dropping his persona on his show. He would never have Paris Hilton on to promote her new fragrance and proceed to grill her on her arrest for drunken driving and her brief experience in jail in such a way that indicts the oxymoron that is “celebrity justice.” Never would he lecture Lindsay Lohan about her responsibility as a role model and the genuine opportunity that rehab can present to her. Nor would Fallon drop his smile long enough to speak unscripted from his grieved heart for eight minutes straight on the first show back after the Sept. 11 attacks. Letterman can surprise in this way too: by getting refreshingly real, in such a way that connects to the viewer who is critical enough of the world he or she inhabits to want to shake these idiots whom we so often grant the power of celebrity and say, Enough Already, or who may not yet be ready to laugh in the wake of tragedy, to offer a smile whose corners didn’t bend with guilt.

Stephen Colbert is arguably America’s greatest living satirist. Going back at least as far as Voltaire and Swift, satire has skewered institutions and individuals on the toothpick-size spear of absurdity. Colbert’s character on "The Colbert Report" was just that, a character, one made up to mock the very conservative views he espoused on a nightly basis. Colbert embodies the beliefs he means to criticize, and he levels that criticism by reducing those beliefs to the absurd. His audience may be composed mostly of liberals who agree with his criticism of conservative buffoonery, but to narrow Colbert’s satire only to the conservative agenda and pundits is to do him a great disservice. For nine-plus years, Colbert masterfully satirized cable news and the American culture obsessed with it. He made fun of us all. And in order for his viewers to enjoy his show—as his ratings and his commercial influence (“the Colbert bump”) prove they did—they had to approach it with vulnerability, a willingness to laugh at themselves.

So perhaps the networks have, for once, accurately identified the needs and wants of its current viewership, as they transition from Leno to Fallon and Letterman to Colbert. Letterman’s old viewers will find companionship in Colbert’s welcoming them in on the lifelong joke of their own absurdity, and Leno’s old viewers will be made by Jimmy Fallon to feel they are smart—or really to feel anything they choose to project onto his smile. These are stark differences in comedic approaches because they are addressing starkly different needs in their audiences. And maybe we shouldn’t be surprised by this. Because here is another pervasive trend in America: We tend to exist more and more at different poles, flocking to the apparent but oversimplified certainty of extremes, and it would seem the case is no different when it comes to the comedy we seek for catharsis, in whatever form, late at night, after long days of dealing with people who seem to be less and less like us in every way but that they too need to laugh.