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What It Was Like Writing Jokes for President Obama

President Barack Obama Photo-Illustration: Getty Images

This interview originally ran in April 2017. We are rerunning it now that David Litt’s book, Thanks, Obama, is in stores.

When Donald Trump announced that he wasn’t going to attend the White House Correspondents’ Dinner, it wasn’t a surprise, considering his thin skin and the time he bombed at the Al Smith Dinner. But it was a bummer. Not just because it would be good TV to watch Trump get made fun of to his face, but because the White House Correspondents’ Dinner is a strange, unique night of comedy. The president, who has the busiest, most consequential job in the world, and who is (usually) not a trained entertainer, has to do a 20-minute stand-up set. And it has to be good.

Behind the scenes, there is a similar contradiction at work: The speechwriters who spend most of their lives writing about tax plans have to turn into the Daily Show writers room for a month. Knowing that the dinner was coming every year, Obama was always sure to have a joke guy on staff. For much of his administration, David Litt was that guy.

On this week’s episode of Good One, Vulture’s podcast about jokes and the people who write them, Litt talks about the nitty-gritty of writing bits for the most powerful person in the world. Specifically, the interview focuses on the 2015 dinner, in which Keegan-Michael Key came out as his Key & Peele character Luther, Obama’s anger translator. The result is an interesting look at high-pressure comedy writing and what Obama was like as a boss.

Listen to the episode and read a transcript of our discussion below. Season two of Good One is set to return in late October. Subscribe on iTunes, or wherever you get your podcasts.

Jesse David Fox: On a basic, biographical level, but also a metaphysical level, what led you to working as a speechwriter with a focus on jokes for President Obama?
David Litt: I had intermittently been interested or disgusted with politics when I was in high school and college. I’d always been interested in comedy, and I was one of those college students who edited a humor magazine and was in an improv group. After I finished my junior year of college, I was trying to figure out what I wanted to do and I saw Obama speak during the primaries. The moment I saw that speech, I was like, “I want to do whatever he’s doing.” So, I worked in Ohio as a field organizer on the 2008 campaign, moved to D.C. because of “Hope” and “Change,” and ended up getting an internship at a speechwriting firm that turned into a job at a speechwriting firm, where they happened to write jokes for politicians. I pitched a few jokes to the Correspondents’ Dinner in 2009 or 2010 and then, when I got this White House job, I was one of the people who they thought, Okay, he can write jokes.

Does the White House usually have a person so joke-focused, or was that something Obama-specific?
Most White Houses think about the Correspondents’ Dinner, but I was not hired as the joke guy. Eleven months a year, I wrote speeches about housing policy or infrastructure. There was one year where I was working on the Correspondents’ Dinner and simultaneously working on a speech about the Holocaust, so it was a very weird headspace to have to spend the morning on one and the afternoon on the other. Our designated funny person was John Lovett. Then he moved to Hollywood to write a sitcom in 2011 and they were like, “Okay, I guess you’re the new token funny guy.”

You said for 11 months of the year, you’re not working on this at all. Did you have notes in your phone to be remember jokes or topics you want to hit?
For a few years, I would try to keep notes running all year long and then I’d have these weird notes in my phone like, “Paul Ryan. Zombie?” Just really dumb. What I found was anything that seems like it’s really current, three weeks later, it’s not. So we really got going three weeks in advance, maybe three and a half.

How does the planning start?
The Correspondents’ Dinner was like a writers room. We had a couple of people inside the building who would pitch jokes. We had this diaspora of people who used to work in the White House — whether that was Jon Favreau, who used to be the chief speechwriter, Jon Lovett, David Axelrod. And we would work with professional comedy writers, whether that was big names like Judd Apatow, or just like someone I went to school with. Let’s say, three weeks out, I would send a list of topics to everybody and we’d slowly get submissions back. While that’s going on, I would also be writing my own stuff.

Every other speech pretty much had one speechwriter, but it would be very, very hard for one person to write the Correspondents’ Dinner on their own. Jokes are just different than speeches in that way. Every line needs to be the best possible version of that line, and it’s all new, it’s all original.

You mentioned Judd. Do you remember jokes Judd pitched you? There was one from 2013 — Judd and Lovett teamed up to write this — where the president said, “Everyone wants to know why am I not doing more outreach to Congress? Why don’t you get a drink with Mitch McConnell? Why don’t you get a drink with Mitch McConnell?” What I noticed was speechwriters tend to be precise about language, but professional comedy writers tend to bring attitude in a different way. That was helpful because we got to do things that we wouldn’t otherwise do.

Part of what made writing jokes for the president a lot easier than writing jokes for a lot of other politicians is that he has that performer’s sense of self-awareness. He could pull off a joke like that because he knows, Okay, this is how I’m being perceived. That is not a requirement to be a senator or a president, but he happened to possess that.

What is it like to write jokes for the president of the United States? Does it ever feel normal, like you’re just writing jokes for anybody?
It never felt normal to me. Maybe some people were like, “Ah yeah, this is no big deal.” I never crossed that threshold. The thing that is very, very different about writing jokes for a president is that, the next day, that person is still the president. So if you say something that breaks some taboo or offends somebody, you’re still on the hook for that. Generally speaking, joke writers are not the type to self-censor constantly, but you have to be thinking in that way to write jokes for a president. Or at least to write jokes for President Obama, who cared about that sort of stuff.

Obama has an interesting persona in all of them. How would you describe it?
President Obama doing these comedy monologues was not terribly different than him as a candidate. It’s a lot of confidence, a lot of intelligence, and then some sense of audience. Obviously I’m biased, but before I was working on the speechwriting team, I always thought he could give a speech where it wasn’t just that you thought, Oh, Obama’s great, but it made you feel really great. And on top of that he has this sense of, Yeah, I’m pretty good and I know it. It was fun to write for somebody who can do both of those things.

I can’t think of a president that had to deal with as many absurd conspiracy theories, and he played with all of them. How deliberate were you guys, like, “Oh, we gotta hit birther, Muslim, socialist?”
Well, it wasn’t like we had a bingo card, but I do think it was a moment to be like, Really? This is happening? One of Jon Lovett’s jokes in 2012 was, “This job has aged me. I look in the mirror and I think, I’m not the strapping young Muslim socialist I used to be.” Lines like that, where you can joke about it rather than vent about it, was a nice sort of release valve.

I imagine there’s a certain sort of paradox in writing for the president. You want to write something that’s funny because the president of the United States is saying it, but you don’t want to write jokes that are funny only for that reason.
Well, when the president tells joke, half of the joke is that it’s the president telling a joke. He’s not going to tell a joke that would be right for Louis C.K. or Seth Meyers; he’s going to tell jokes that make sense for him. In that sense, it is also a little bit liberating.

We had at least one Oval Office meeting where we were going over jokes, and we had one that went a little bit too far on the performing element where the president wasn’t just playing the president, but we were asking him to kind of play a character. And at the end, he sort of looked at us and said, “That would be funny, if a comedian did it.” And we’re like, okay, message received.

At what point are you involving the president?
Usually we would have these topics, get submissions, and bring everything together. Let’s say, 600 or 700 jokes total come in. We end up with about 40, and those we would bring to the president. Some years, we would bring them as a list. Some years, we would try to do a script. He’d read through them and cut, let’s say, ten that he isn’t liking. There’s usually a few more where he’d say, “This is pretty good, but maybe we could do better on this,” or make a series of frantic notes next to that joke in the script. And then we’d go back and do another, at least two, sometimes three meetings.

At what point was the first meeting?
The dinner’s always on a Saturday, so the first meeting was usually Tuesday or Wednesday.

Did you have certain big swings in there? Was he willing to allow you guys to push the envelope, at least with him?
Oh, for sure. The danger was not disappointing him; it was taking up his time. If he’s wasting five minutes reading jokes he doesn’t like, that’s five minutes that could be spent on, like, Afghanistan. For him, it was never an issue of trying to scale us back; it was usually the opposite. He would read something and say, “This is pretty good, but could we go a little edgier, a little sharper with it?” “Sharper” and “edgier” were his two big notes, so you went back to your office feeling free to take an even bigger swing.

Let’s talk about Luther, Keegan-Michael Key’s anger translator character from Key & Peele. The character had been around for years at this point, and Obama has already said he liked him. What was the germ of the idea to make it happen in 2015?
We wanted to do this every year. The first year I was responsible for the joke writing process was 2012, and even then we said, “Should we get Luther the Anger Translator?” Then we thought about it and said, “This is an election year. Maybe we don’t want to risk it.” In 2013 and 2014, it didn’t really feel right. And then, in 2015, we had this attitude of, All right, we’re just going for it. It’s the fourth quarter of the presidency, we don’t care anymore. That was the big national story: Obama’s liberated, he’s doing whatever he wants. So this seems like the perfect time to do it.

What was the process of writing it once Keegan agreed to do it?
I assumed that Keegan and their team would just be like, “Okay, we’ll handle this from here,” but he was like, “Why don’t you guys do it?” So it’s trying to write for both the president’s voice and this voice of a character you really enjoy, but you’ve never written for. I wrote a draft, and then sent that to some of our sort of most trusted comedy people. We sent it back to Keegan, he made some edits and so on. Three to four days before the speech, the president knew we were going to do it. He was excited, but he hadn’t seen the script, so we brought that in and he took a look at it for the first time.

What’s the rehearsal process like?
Pretty abbreviated for something like this. The president read through the lines with us once or twice before.

You’re playing Luther?
No, he would do both. I think he actually kind of liked the chance to be in the room playing Luther. That was Thursday or Friday. Saturday, the day of the dinner, we only had 20 minutes to get it right. At about 4 o’clock, we smuggled Keegan into the West Wing — making sure that no journalists would see him — and then around 6, we figured, Okay, the journalists are all going to their parties, we can bring him out. We brought him over to the Map Room, which is one of the rooms, which has all these World War II maps and these old, fancy Colonial maps. We had the setup with the podium, and the president came in and we just started. We did it once and then, briefly, they made a couple of notes and then we did it again. And that’s it. You get in a motorcade and you go.

Is it on you to give the president notes if his performance is off? It is, but for the most part, you’re careful with stuff like that because you don’t want to act like he’s an actor. I mean, his job is to be the president and he happens to be there telling jokes. If something had been wildly off, it would have been my job to say, “You know, Mr. President, this is not going to work if we do it this way.” If it’s like, “Oh, this could be slightly funnier if you really hit that last word in a joke rather than the first word …” that’s a point where you keep your mouth shut and say, “He’s got other things to worry about.”

Were there specific beats that you were excited to try when you were scripting it?
I was excited about making sure we could build in a twist at the end where the president gets really angry. That, to me, was fun both because I felt it would be fun for him, but also because there is a moment to talk about something real. In this case, we’re talking about climate-change deniers in Congress to let POTUS get really angry in a way he probably would in private, and then also help answer the question, Why is this different than the same Luther the Anger Translator sketches we see on TV? Doing both of those things seemed important to me.

I don’t think I’ve ever heard Barack Obama talk that way. Because he’s playing a part, they all allowed it, but that might have been the angriest he ever was on TV.
Obviously he’s playing a character, even though that character is himself, but that’s probably the most angry he got in public. I think that is one of the reasons he was excited about doing it. It was a chance to let loose a little bit.

Do you remember the response in the room?
I remember the first moment Luther walked out onstage, and Keegan was really milking every single step. A third of the people in the room were like, Oh my God, I dreamed of this moment. And then a third of the people in the room were like, I’m not sure about this. And a third of the people in the room were like, Who is this guy, and what is going on? Because the Correspondents’ Dinner audience runs the gamut. There was this weird tension and it took a couple of lines for that tension to break. Once people realized what was happening and felt like, Oh, we’re in the middle of something special, then you started to see people get really excited about it. At the very end — when the president got really upset about climate-change deniers and Luther’s trying to calm him down — there was a moment where there were a lot of people on their feet, both because they enjoyed it, but also they felt like it had done this bank shot, where now we’re talking about something real.

Keegan Michael-Key as Luther jokes about it when he says, “Really, what is this dinner?!” The question I want to ask you more than any other is why? What’s the point of this event existing? What’s the point of a president doing this?
It’s important that a president does something like this because there’s this relationship we have between the press and the president and the country. Every president thinks the press is unfair and the press always thinks the president doesn’t give them enough access and is trying to keep them from doing their jobs. That’s just the way it is. But on this one night, everyone sort of says, “In our own way, each of us is important to democracy.” That’s one important element of it.

To me, the other important thing is it’s a chance for the most powerful person on Earth to tell some jokes and, usually, tell some jokes at their own expense. We would have millions of people watch these things on YouTube — not just in the United States, but in countries like China, where the idea that your leader would tell a joke or acknowledge a vulnerability or be anything other than this kind of demigod totally blew people’s minds. Just the fact that he was up there telling jokes. That was something that was really exciting about the Correspondents’ Dinners, writing aside. Just this moment where we got to say, the president of the United States is going to acknowledge, Hey, I’m only human. We’re all here to laugh.

Which brings us to the current president. What was your reaction to President Trump’s decision not to attend the Correspondents’ Dinner?
It’s not so much that it’s a bad decision. Donald Trump is a bad person and that is reflected in his decision-making. I don’t say that lightly. I don’t say that a lot of people are bad people. What I mean by that is, he does not understand the value of a free press. He doesn’t understand the value of being able to joke about yourself or admit that it’s a democracy. “I’m the president, I’m the leader, but I’m also just a citizen and I work for you, not the other way around.” So all of that together makes him say, “Why would I go to an event like this?” not as a joke, but for real. “These people are out to get me. I’m not going to be adored and loved unconditionally. I’m going to have to earn it, so I’m just going to skip it.” That is a real shame and it sends a bad message. It’s not the worst message he’s sent, but I don’t think it’s a good message to other countries. It was a chance for us to show that you can be more powerful than your second-rate dictator and more human. Instead, we’re sort of saying, maybe that’s not a possibility.

Were you surprised that he decided not to do it?
Honestly, I wasn’t totally surprised. He does all sorts of things that don’t really make a lot of sense or that I don’t agree with. Though, it wouldn’t surprise me if we get into a “Is he going to show up at the last minute?” controversy to get a lot of retweets or something like that in the next couple of days. I’m not sure what’s going to happen, but it wouldn’t surprise me to see anything that keeps the attention on him, which you would think you don’t need to do when you’re president.

And yet.
One other thing that I wanted to add. Did you see the Al Smith Dinner?

Yes, right before the election.
Hillary and Trump both told jokes. Maybe that event was the one they should have canceled. He didn’t do very well. He had one good joke that was at his wife’s expense and everything else … he got booed in the room. I wrote jokes for President Obama at the Al Smith Dinner. I don’t think a lot of them necessarily voted for him, but it’s hard to not get some polite applause in that room. I think that experience of the elite of the media world, of the New York world, the finance world all booing him, he got a little skittish about what’s going to happen if I show up at the Correspondents’ Dinner?

Do you remember Obama’s absolute favorite joke you wrote for him?
The joke I wrote that he liked the most was from 2013, when he said, “You know, Republicans all agree they need to do a better job of reaching out to minorities. Call me self-centered, but I can think of one minority they should start with.” And that was fun because he liked that enough that he was like, All right, I might do a little wave in there. And I think he ad-libbed something like, “Think of me as a trial run.” It was fun when he would play off something like that.

Is there a joke that you always thought was funny that everyone else thought was terrible, but you still think that’s a really good joke?
One that I wrote every year to see if people wouldn’t notice that I’d already written it, was something like, “You know, I think no matter what else happens, I’m going to go down in history as America’s first black president.”

That’s a good joke!
Every year I tried, every year no one liked it. There’s a certain point you have to be accepting of the fact that you get to write for the president, but they’re not your words. You may think that’s great, but if the world doesn’t seem to agree, you drop it.

What It Was Like Writing Jokes for President Obama