How David Letterman Changed Late Night

He made Jimmy Kimmel’s political monologue possible. But did he also play a role in normalizing Donald Trump?

Jimmy Kimmel
Jimmy Kimmel

Randy Holmes/NBC

Jimmy Kimmel’s passionate and surprisingly political account of his newborn son’s emergency heart surgery has gone viral this week. It’s hard to imagine a similar monologue from Johnny Carson, but the current crop of late-night hosts have adapted to their times, and their politics and personal lives have become a larger and larger part of their public personas. The man who is as responsible for this change as any other was David Letterman, the subject of Jason Zinoman’s new book, Letterman: The Last Giant of Late Night, which examines the comic’s long career and impact on television.

I spoke by phone with Zinoman, who writes the New York Times’ “On Comedy”’ column, recently. During the course of our conversation, which has been edited and condensed for clarity, we discussed how Kimmel found mainstream success, Jimmy Fallon’s controversial approach to comedy, and how Letterman would have dealt with a President Trump.

Isaac Chotiner: How much do you think Letterman is responsible for the fact that late-night hosts give monologues like the one Kimmel gave this week?

Jason Zinoman: I think Kimmel’s performance, which was stunning, owes a huge amount to David Letterman, and owes a slightly smaller amount to Jon Stewart. Jimmy Kimmel once said that Letterman was more important than sleep to him. He called him “my Jesus.” He reveres David Letterman and surrounds himself with people who like Letterman and in some cases are former employees of David Letterman. He started his show only a few years after Letterman gave his own speech about heart surgery, and it’s hard to watch Kimmel’s wonderful performance and not see echoes. The way that Kimmel listed all the doctors: Letterman did that about his heart surgery. And I think more broadly, Letterman in the late 1980s started to turn the talk show into a reality show of sorts, where the host is the star. His relationship with his mother becomes a big subplot. He had regular flirtatious conversations with Meg Parsont, who worked in a building across the street, a stand-in for a romantic interest.

Or even Julia Roberts.

Yeah Julia Roberts. He has these feuds with Oprah or whoever. This is before The Real World premiered. Part of the reason people love reality shows is the same reason they got interested in Late Night. And what you see with Kimmel, who apes a lot of Letterman’s style, is that he is using his life, or this traumatic event, or the birth of his kid—which Letterman also talked about on-air—for a long story that works in the context of a talk show. Letterman would generally use it for comedy, even a woman stalking him or breaking into his house. And this is where Jon Stewart comes in. Kimmel pivots to weaponize this story, pretty stunningly, to inject himself into a political discussion about health care that is relevant right this second, and that’s something Letterman didn’t do.

So Letterman never did that, as far as you can remember?

In the 1980s it was hard to know what Letterman’s politics were. You could have watched his show and thought he was a conservative. And in the 1990s it was also hard to tell. And starting with the Iraq war, his politics became more clear and more overtly liberal. I think the influence of Stewart changed the calculus for a lot of people. And Letterman paid the price for that, to some extent. I did a lot of reporting in Indiana, and a lot of people in his fan base were alienated by this. His fan base included liberals and conservatives. Rush Limbaugh was influenced by him and was a guest. So if you look at his whole career, he didn’t foreground politics, and nor does Kimmel in the way of Colbert or Stewart. So it was out of character for Kimmel to do this.

When you say that Letterman’s politics became more clear, do you mean that they changed or that he became more clear in expressing them?

I think it was that he was willing to talk more about it on-air. From my reporting, I don’t think Letterman was ever a conservative, but he would make fun of self-righteous lefty liberals, and he positioned himself early on as a heartland and Middle America kind of guy. His writing staff had some Republicans and conservatives. But I don’t think his politics radically changed, and they were never far left or far right. To the extent he was politicized, it was the Iraq war and then Sarah Palin.

Was Stewart’s tearful post–9/11 monologue the beginning of that sort of emotional monologue on late night, or were there earlier examples?

There is a kind of pre-history of hosts getting emotional. The real godfather of this was Jack Parr, who told Letterman that it’s OK to show anger on air. He famously quit The Tonight Show on air because he was banned from making a joke about a water closet, which now seems silly. Carson would occasionally talk about his marriages, but he was pretty much the opposite of emotional. I think the heart surgery for Letterman in 2000, and then 9/11, that performance, really was a turning point. You started to see that as part of the repertoire. Part of the reason Letterman had such an impact when he did these things was that he was known for being such a guarded performer. So when you saw him get emotional, you believed it, and it had an impact. Now it has become more common, and I wonder whether it will have less of an impact.

How do you think Kimmel has changed as a performer? This is a guy who was co-hosting The Man Show.

It’s actually a remarkable transformation, considering the current climate. To go from The Man Show to hosting the Oscars is not easy.

Adam Carolla will not be hosting the Oscars anytime soon.

Exactly. Someone like Howard Stern has made a similar transition and gone more mainstream, and there is some controversy among his fan base about this. But he has never gotten to the point where people are asking him to host the Oscars or giving these kinds of political speeches. If you look at interviews from when he left The Man Show, clearly Kimmel did not want to be known as the host of a loutish variety show. So he made these moves to change his persona, and to a large degree he has succeeded. He is not beating Fallon or Colbert in the ratings, but I do think he has inherited a lot of the Letterman role in the cultural marketplace. He does perfectly respectably. Just see how he has changed his looks. He has become a very slick, handsome-looking guy. And now he is sticking his neck out on this political issue, where only a dozen years ago that would have seemed highly unlikely. I do wonder if there will be a backlash to this.

Do you see any similarities between his transformation and Letterman’s? Letterman wasn’t ever loutish maybe, but he became more mainstream, and his rough edges were sanded in some ways.

I …

Or maybe that’s wrong.

I think that’s wrong. I think it has things backwards. The truth is that Letterman in the 1980s was the coolest performer on television. He had all the hipster credibility you could want and was in opposition to Carson, whereas Kimmel, because of The Man Show, had an audience but had no cool cred, and he certainly had none of the politically cool cred that Stewart had. You are right that they both went through a transformation, and Letterman moved from a more artistically adventurous and experimental show to becoming one more about himself and in a way more human, with his personality more center-stage. Kimmel has in some ways a tougher task, because he had to win over people—which I don’t think he has completely done—who don’t think he is as cool as Colbert. And I think for some people he is not even as cool as Fallon.

Those Fallon people should be stripped of their citizenship, and their opinion doesn’t matter.

In today’s landscape, the coolest thing in the world is to shit on Fallon.

Well he is terrible. That’s why it’s cool.

What’s the argument for why he’s terrible? That he rubs Donald Trump’s hair?

Yeah, that’s a good place to start.

I think Fallon—the games, the turning late night into a kid’s birthday party is what bugs me. It was remarkable to watch his monologue on Saturday Night Live last week. There were no jokes or perspective. It’s just singing a song. He has drained comedy out of late-night comedy. It’s kind of a remarkable moment where a late-night host did a monologue without a single attempt at being funny. The attempt is to be fun, not funny.

The usual analysis is that, ratings-wise, that was smart before Trump came along, and now people want something spikier, and Colbert is beating him in the ratings. Do you agree with that argument?

Yeah, I think we have gotten into this much more fragmented era where you have very political humor, from Samantha Bee and John Oliver, with a left-wing slant, and then you have Corden and Fallon going for these viral-fun effects. To the extent that Colbert is on the rise, it has been his ability to straddle these worlds. Colbert has the potential, unlike Fallon, to be both politically righteous and sharp and to be silly and fun. Which makes him a man for his time. Whether Kimmel can also do that—I think perhaps he could. The real question is whether, if Fallon starts losing more, how does he adjust? Can he do anything but fun? Can he get more political on the show? I don’t know if I want to see that version of Fallon. But if you are playing the long game, at some point Trump will be out of office.

You are so optimistic, Jason.

Good point. There might come a point where people at late night are going to want to watch more escapism, and if that’s the case, Fallon is well-positioned in that audience.

That’s quite a moral dilemma: have Trump remain president forever, or see Fallon succeed. How do you think Letterman would be handling Trump if he were on air?

That’s a good question, and I actually think that while a lot of Letterman fans like to think that he would have the most trenchant stuff on Trump and go after Trump the way others wouldn’t, I am actually skeptical of that. I don’t think it’s in his comedic DNA to do exactly what Bee and Oliver do so well. I think he was a different kind of performer. Letterman has a long, long history with Donald Trump, which spans from 1985 until the end. In some ways Donald Trump was introduced to the mainstream on television through appearances on Letterman’s show. I am inching towards doing the most Slate thing possible, which is to defend Jimmy Fallon, but you could make an argument that Letterman’s shows normalized Trump as much if not more than Fallon.

But Trump wasn’t a racist lunatic in the 1980s, or people didn’t know he was, right?

Well, I don’t know. The Central Park Five happened a long time ago.

That’s a good point.

Letterman called Trump a racist on-air and then had him back on the show, several times.

When was this?

When the birther thing happened.

Let’s put it this way: I think Letterman would have definitely had some wonderful, hard-hitting comedy about Trump, and that would have been great. And no one on television now is better than Letterman at long-form conversation. He would skewer Bill O’Reilly better than anybody. But I think people who think that Letterman would stand apart from the other politically minded comics—I don’t think there is evidence to support it.