How to make a funny president

Sam Stein: Okay, let’s establish your credentials. What did you do in the White House?

David Lit: I was Obama’s speechwriter. It started in the White House in 2011, lasted until 2016. I cracked jokes, actually, during the Obama years, but for four of those years — from 2012 to 2015 — I was sort of the person running the Correspondents’ Dinner from inside the building. I’d probably been more stressed by it than most people. Not everyone, but most people in politics. I’m pretty sure I’m the only person who’s ever had to buy one of these anti-grinding mouthguards.

Stein: You didn’t buy one of these! You did?

A little: I absolutely did. It’s an intense speech to get right, and it’s hard to prepare. Also, you know, I was in my 20s.

Stein: A young guy when you were writing this?

A little: Yeah, so I had no business doing what I was doing. And I think my teeth knew it, even if my brain didn’t.

Stein: What is the key to writing a good funny speech for a politician?

A little: Well, I think the key, first of all, to writing anything that’s funny is writing tons of non-funny stuff, and then choosing the good stuff. There is no shortcut. The most important thing about writing funny things for politicians is that the joke fundamentally is that the president is telling jokes, right? That’s the joke of every joke.

Stein: So it’s about self-awareness, essentially?

A little: Self-awareness is something that throws away all the things we already know about that person. A comedian’s personality is that he is funny; the personality of a president is that they are serious. And so you’re throwing it away all the time. So that means that some things that would work very well for a president would work terribly for an evening presenter, and some things that would work perfectly for a night presenter would actually be a total failure if a president said that.

Stein: You wrote to Obama, which I felt was naturally comical. But this is not the case for all politicians. Is it possible to make a dull politician funny?

A little: Well, you know, with President Obama, he’s such a good, natural artist. His timing was so good that you could give him things that really depended on timing. I didn’t write that joke, but there was a great joke in it – I don’t even remember the words, but the joke was just a big wink. That’s not something you could give all politicians.

I think you can make almost any politician the funniest version of themselves, but that means a lot of different things depending on who you’re talking to. I think – particularly for things like Gridiron, or for some of the many, many weird comedy events scattered around DC for some reason – people get a huge amount of credit for showing up. And they deserve it. This is not something that most people, most political figures, do on a regular basis. And so, everyone knows that there are people stepping out of their comfort zone, avoiding reputation risk, right?

Stein: What is an example of a joke you pulled?

A little: The ones I think of are not actually jokes about national security things, because I think people knew better. Every year we got some jokes about [former New Jersey Gov.] Chris Christie being a bigger guy, and that was the joke. And we thought, “We’re not going to take this to the president. He won’t say that.” I’m sure there was something specific, you know – like jokes about foreign leaders that we just wouldn’t do.

You know the president is mostly the president – ​​and then, you know, an occasional comedian. And that actually goes back to your first question about writing speeches for politicians: Fundamentally, like any speech, a comedy speech should help them even more, whatever their goals.

Stein: What is the purpose of a White House correspondent’s speech?

A little: I think there are a couple of different things.

Stein: Is a goal just to have fun?

A little: I think the biggest thing is that there’s a sense of authority that comes from being able to make a room full of people laugh. That’s not how I would describe it in a meeting at the time, but we tend to like our political figures to be a little cold. And so, if you can demonstrate that you can laugh at things, that’s usually very helpful.

And sometimes we would address specific political points, as we did with Luther, the translator of anger. Keegan-Michael Key, who was brilliant, came in and played Luther, his character, with President Obama. But the end of that was a little bit about the climate deniers and how upset President Obama was at the climate deniers. So there’s a chance to say something real that we probably couldn’t have said. He couldn’t have been as angry as he actually was in a speech, but he could have done it as a joke.

Stein: What’s the best joke you’ve ever written for a politician?

A little: I get this question and I give this answer and nobody laughs. But I keep that joke. In 2013, it was shortly after [Republican presidential candidate Mitt] Romney had lost and Republicans released his autopsy saying they had to do better with minority voters, especially Hispanic and Latino voters. And then Obama said, “One thing all Republicans seem to agree on is that they need to do a better job of reaching minorities. Call me self-centered, but I could think of a minority they could start with.”

And I loved that joke. And I also loved it because I think it was the first or only time – maybe I’m wrong about that – but it was certainly one of the only times the president referred to himself as a minority. It was not transgressive to a large extent. But I was pushing the envelope a little rhetorically at him. So it was surprising. He liked that joke a lot too. If he really liked a joke, he added stuff. So he liked a little wave, you know? That was an improv, which is how you know he really liked something.

Stein: Who do you think is the worst political joke-teller in history?

A little: That’s a great question. I bet on Herbert Hoover. I read some of your Correspondents Dinner stuff. I’m sure it was him. And to be fair, the Correspondents’ Dinner used to be so into baseball. So he would crack jokes that were like, you know, “I know Aldo Beckman brought his swizzle stick” or something. I don’t know if it made the room laugh.

Calvin Coolidge was very funny or there were many very funny stories about him.

Stein: Yes, “Silent Lime”. He wasn’t a big projector.

A little: There’s a whole genre of Coolidge jokes at the time.

Stein: I honestly can’t tell if you’re serious.

A little: Oh no, that was true. It’s like a famous story where someone – I think it was at a White House dinner – said to President Coolidge, “I made a bet with my friend that I could make you say three words at this dinner.” And he turned to her and said, “You lost.”

Stein: What do you think Trump would have been like if he had actually spoken at one of those dinners? I mean, we know he made Al Smith’s dinner, and I thought he was funny at times and deeply disturbing at other times, like a little cruel. But that’s kind of Trump, right?

A little: Yes, I’d say the ratio of deeply disturbing to funny was 90 to 10. The Al Smith dinner…again, people get credit for showing up. And he was booed a lot at Al Smith’s dinner. This is the first time, and this is really hard to do.

Stein: Well, he took some real partisan blows, if I remember correctly.

A little: One of his quote-unquote jokes was, “Hillary hates Catholics,” right? And people would say, “This is totally disgusting, it’s inappropriate.”

Stein: It’s not very funny either. It’s not just a joke.

A little: It’s not funny, it’s just weird. This is the coolest thing I’ll say about Donald Trump: he had a good joke, and it was at his wife’s expense. Remember, why did Melania Trump plagiarize Michelle Obama’s speech? And he said, “You know, Michelle Obama gives this great speech, everybody loves it. My wife makes the exact same speech and you all complain!” Which I thought was a good joke.

And I think that’s the reason he didn’t go, because if you look at 99% of Trump’s speeches, they went to friendly crowds as president.

Stein: I disagree. I don’t think he wanted to be roasted.

A little: Well, I think that’s true, too. I don’t think he wanted to be exposed to whoever the comedian was.

I don’t think presidents necessarily crave the Correspondents’ Dinner, but they feel it has some value in a democracy, because A, it’s important that the leader of the free world can make fun of himself, and B, it’s important to recognize that a free press is important for democracy. And I don’t think Trump felt that way about any of those things.

Stein: Can you recommend a favorite example of political comedy for our readers?

A little: First, obviously, the book would be Thank you Obama. You know, “I’ve heard nothing but good things,” a lot of people are saying. [Laughs.] But the clip I would recommend – I haven’t seen it in a while, and some of your younger readers may not have – is to go back and watch Stephen Colbert at the 2006 Correspondents’ Dinner. Now every comedian wishes they could be [Ukrainian President Volodymyr] Zelenskyy, but before that, I think it was – I’m going to misuse that word, I’ll bet – the apotheosis of a comedian using his platform to say something really funny. And also speaking truth to power.

Stein: This was a deeply controversial speech at the time.

A little: In the room was very controversial.

Stein: For the reader, we must establish what he did: he essentially destroyed the administration and its handling of a whole series of things, most notably war.

A little: Yes. But you know, I think the important thing is that he was wild, but those were good jokes. They landed because there was a kernel of truth – often a spike full of truth – in just about everything there. And they were very, legitimately funny, right? It wasn’t just bittersweet or like, “You’ll only get the joke if you agree with me.” You might think, “Well, I hate that prospect. But okay, it’s kind of funny.”

I also think Michelle Wolf at the 2018 dinner was very interesting. I think she said some very interesting things. And important things. And it was completely closed.

Stein: For the comments about Sarah Huckabee Sanders?

A little: What she said was really important to look at the reporters – and also, by the way, the people who wrote books about these things, right? I wasn’t immune to it. And she was kind of saying, like, you all pretend to hate Trump, but you love Trump because he helps you sell your books and get on TV and all that stuff. And I think she was saying something important about media and the way media works. And then immediately people focused on other things. I wouldn’t have written every joke she told exactly the way she told it, but I think this was also one of the most important speeches of the Trump era, even if I don’t think the history books will remember it.

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