David Litt, the author of the New York Times best-seller Thanks, Obama, a comedic White House memoir, was a speechwriter for the former president from 2011 to 2016. For several of those years, he ran point on the White House Correspondents’ Dinner, fielding jokes from speechwriters and developing material for the president. Ahead of this year’s dinner, we had Sam Stein catch up with Litt about how to make a president funny, what made Barack Obama a “natural performer” and Donald Trump’s one good joke.
This transcript has been edited for length and clarity.
Sam Stein: Alright, let’s establish your credentials. What did you do in the White House?
David Litt: I was a speechwriter for Obama. Started in the White House in 2011, lasted until 2016. I pitched jokes, really, throughout the Obama years, but during four of those years — 2012 through 2015 — I was kind of the person running point on the Correspondents’ Dinner from inside the building. I had probably stressed out more about this than most people. Not everybody, but most people in politics. I’m almost sure I’m the only person who’s ever had to buy one of those anti-teeth-grinding mouth guards.
Stein: You did not buy one of those! Did you?
Litt: I absolutely did. It’s an intense speech to get right, and it’s hard to prepare for. And also, you know, I was 20-something.
Stein: A young lad when you were writing these?
Litt: Yeah, so I had no business doing what I was doing. And I think my teeth knew that even if my brain did not.
Stein: What’s the key to writing a good funny speech for a politician?
Litt: Well, I think the key, first of all, to writing anything that’s funny is to write tons of not funny stuff, and then pick out the good stuff. There’s no shortcut. The most important thing about writing funny things for politicians is that the joke fundamentally is that it’s the president telling jokes, right? That’s the punchline of every joke.
Stein: So it’s about self-awareness, essentially?
Litt: Self-awareness and something that plays off all the things that we already know about this person. A comedian’s persona is that they’re funny; a president’s persona is that they’re serious. And so you’re playing off that the whole time. So that means that some stuff that would work really well for a president would work terribly for a late-night host, and some stuff that would work perfectly for a late-night host would be really just a total failure if a president said it.
Stein: You wrote for Obama, who I felt was sort of naturally comedic. But that’s not the case with every politician. Is it possible to make a non-funny politician funny?
Litt: Well, you know, with President Obama, he’s such a good, natural performer. His timing was so good that you could give him things that really depended on timing. I didn’t write this joke, but there was a great joke where — I don’t even remember the words, but the punchline was just a big wink. That’s not something you could give every politician.
I think you can make almost any politician the funniest version of themselves, but that means a lot of different stuff depending on who you’re talking to. I think that — particularly for stuff like the Gridiron, or for some of the many, many weird comedy events sprinkled throughout D.C. 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 regularly. And so, everybody knows that there are people stepping outside their comfort zone, shirking reputational risk, right?
Stein: What’s an example of a joke you pulled back?
Litt: The ones that I think about actually are not jokes about, like, national security stuff, because I think people knew better. Every year we would get some jokes about [former New Jersey Gov.] Chris Christie being a bigger guy, and that was the punchline. And we’re like, “We’re not going to bring that to the president. He’s not going to say that.” I’m sure there were specific, you know — like jokes about foreign leaders that we just wouldn’t do.
You know that the president is mostly the president — and then, you know, an occasional comedian. And this actually goes back to your first question about writing speeches for politicians: Fundamentally, like any speech, a comedy speech should help them further whatever their goals are.
Stein: What is the goal of a White House Correspondents’ speech?
Litt: I think there’s a couple of different things.
Stein: One goal is just to have a good time?
Litt: 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. This is not how I would have described it in a meeting at the time, but we tend to like our political figures to be kind of chill. And so, if you can demonstrate that you can laugh about stuff, that’s often really helpful.
And sometimes we would bring up specific political points, like we did with Luther, the anger translator. Keegan-Michael Key, who was brilliant, came in and did Luther, his character, with President Obama. But the end of that was a bit about climate deniers and how pissed off President Obama was at climate deniers. So, there’s a chance to say something real that we probably couldn’t have said. He couldn’t have gotten as angry as he got for real in a speech, but he could do it as a joke.
Stein: What’s the best joke you’ve ever written for a politician?
Litt: I get that question and give this answer and no one laughs. But I stand by this joke. In 2013, this was right after [Republican presidential candidate Mitt] Romney had lost and Republicans had released their autopsy saying that they had to do better with minority voters, especially Hispanic and Latino voters. And so Obama said, “One thing Republicans all seem to agree on is that they need to do a better job reaching out to minorities. Call me self-centered, but I could think of one 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 this — but it was certainly one of the only times that the president referred to himself as a minority. It wasn’t transgressive in a big way. But it was pushing the envelope rhetorically a little bit for him. So it was surprising. He liked that joke a lot too. If he liked a joke a lot, he would add stuff. So he did like a little wave, you know? That was an ad lib, which is how you know he really liked something.
Stein: Who do you think is the worst political joke teller in history?
Litt: That’s a great question. I bet Herbert Hoover. I’ve read some of his Correspondents’ Dinner stuff. I’m pretty sure it was him. And in fairness, the Correspondents’ Dinner used to be so inside baseball. So he would tell jokes that were like, you know, “I know Aldo Beckman’s brought his swizzle stick,” or whatever. I don’t know if it got a laugh in the room.
Calvin Coolidge was either really funny or there were just lots of really funny stories about him.
Stein: Yeah, “Silent Cal.” He was not a big projector.
Litt: There’s like a whole genre of Coolidge jokes at the time.
Stein: I honestly can’t tell if you’re serious.
Litt: Oh, no, this was true. There’s like a famous story where somebody — I think it was at a White House dinner — said to President Coolidge, “I made my friend a bet that I could get you to 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 had he actually spoken at one of these dinners? I mean, we know he did the Al Smith dinner, and I thought he was both funny at times and deeply unsettling at other times, like a little vicious. But that’s sort of Trump, right?
Litt: Yeah, I would say the ratio of deeply unsettling to funny was like 90 to 10. The Al Smith dinner … again, people get credit for showing up. And he got badly booed at the Al Smith dinner. That’s a first, and that is really hard to do.
Stein: Well, he took some real partisan whacks if I’m remembering well.
Litt: One of his quote-unquote jokes was, “Hillary hates Catholics,” right? And people were like, “This is totally gross, it’s inappropriate.”
Stein: Also just not really funny. It’s just not a joke.
Litt: It’s not funny, it’s just strange. This is the nicest thing I will ever say about Donald Trump: He had one good joke, and it was at his wife’s expense. Remember, because Melania Trump had plagiarized Michelle Obama’s speech? And he said, “You know, Michelle Obama gives this great speech, everyone loves it. My wife gives the exact same speech and all of you 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 percent of Trump’s speeches, they were to friendly crowds as president.
Stein: I disagree. I think he didn’t want to get roasted.
Litt: Well, I think that’s true, too. I think he didn’t want to be sort of exposed to whoever the comedian was going to be.
I don’t think presidents necessarily look forward to the Correspondents’ Dinner, but they feel that it has some value in a democracy, because A, it’s important that the leader of the free world can make fun of himself or herself, and B, it’s important to recognize that a free press is important to democracy. And I think Trump didn’t feel that way about either of those things.
Stein: Can you recommend a favorite example of political comedy for our readers?
Litt: First of all, obviously, the book would be Thanks, Obama. You know, “I’ve heard nothing but good things,” many people are saying. [Laughs.] But the clip I would recommend — I hadn’t seen it in a while, and some of your younger readers may not have seen it at all — is to go back and rewatch Stephen Colbert at the 2006 Correspondents’ Dinner. Now every comedian wishes they could be [Ukrainian President Volodymyr] Zelenskyy, but before that, that I think was — I’m gonna misuse this word, I bet — the apotheosis of a comedian using their platform to say something that was really funny. And also speaking truth to power.
Stein: That was a deeply controversial speech at the time.
Litt: In the room it was really controversial.
Stein: For the reader, we should establish what he did: He essentially tore apart the administration and its handling of a whole host of things, primarily the war.
Litt: Yeah. But you know, I think what’s important is, he was savage, but those were good jokes. They landed because there was a kernel of truth — often a full cob of truth — to just about everything in there. And they were really, legitimately funny, right? It was not just sort of bitter or like, “You’ll only get the joke if you agree with me.” You may be like, “Well, I hate that perspective. But OK, it’s kind of funny.”
I think also, Michelle Wolf at the 2018 dinner was really interesting. I think she said some really interesting stuff. And important stuff. And it got completely sort of shut down.
Stein: By the comments about Sarah Huckabee Sanders?
Litt: What she said that was really important was looking at the reporters — and also, by the way, people who have written books about this stuff, right? I was not immune to this. 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 of this stuff. And I think she was saying something important about the media and the way the media functions. And then immediately people focused on other stuff. I would not have written every joke she told exactly the way she told it, but I think that was also one of the more important speeches of the Trump era, even though I don’t think the history books will remember it.