What it’s like to write jokes for President Obama

David Litt's new memoir reflects on what he learned from *just* outside the president's inner circle.

Keegan-Michael Key, David Litt, and President Barack Obama before the 2015 White House Correspondents Dinner. CREDIT: Courtesy of David Litt.
Keegan-Michael Key, David Litt, and President Barack Obama before the 2015 White House Correspondents Dinner. CREDIT: Courtesy of David Litt.

David Litt wants you to know he wasn’t that important.

Yes, he was a speechwriter for President Obama. But “speechwriter” encompasses a whole range of formats beyond the iconic, rhetoric-to-the-rafters stuff that POTUS famously delivered. Though Litt lent his efforts to more traditional presidential addresses, working his way up to Special Assistant to the President and Senior Presidential Speechwriter status, he spent much of his time crafting missives like debate zingers (one of Litt’s favorites: “Why is Governor Romney keeping all his plans secret? Is it because they’re just too good?”); jokes for the White House Correspondents Dinner (this used to matter because the president traditionally attended and performed there, though who knows if that will ever happen again); and well wishes for birthdays and holidays (it turns out even Obama struggles to get out that “ch” sound in chag sameach).

Litt’s memoir, Thanks, Obama: My Hopey, Changey White House Years, reads like tales from the not-quite-inner-circle: Someone who found himself in the Oval Office more than once, but was feel-like-an-idiot nervous almost every single time he spoke with President Obama. But Litt’s book does capture the fact that much of government work is about as glamorous as the average episode of Parks and Recreation (at least, aside from a few glimpses at the parts of White House life that are, in fact, as cool as one would imagine — Air Force One, he promises, lives up to the hype) .

Almost two years have passed since David Litt worked in the White House. He’s still adjusting to the slower pace, to not thinking that “the moment someone emails you, email them back immediately because the world might be on fire,” he said by phone. Litt, who’s now the head writer and producer for Funny Or Die in D.C., reflected on life in and after the White House and just how hopey changey he’s been feeling since his boss’ successor took office.


My understanding is that most people writing memoirs about politics generally try to make themselves sound as important as possible, like they were always in the center of the action (even if that wasn’t the case). But this is a very self-effacing book. How did you decide to write it?

The way I thought about it wasn’t like, how much gossip do I have? Because I don’t have very much and wouldn’t be interested in writing that kind of book anyway. I thought, I have all these fun stories about times I embarrassed myself in front of the president. I’ve enjoyed telling them to friends. So I thought, what’s the right way to share them with everyone?

I did standup in college and improv comedy, so my original thought was, I should do a one man show… And after Trump was elected, writing a book took on a new urgency. [I wanted] to remember what it was like when the White House was run by people who actually cared about making America better.

Is it especially cringe-worthy for you, as a speechwriter, to watch Trump’s public addresses? He does not appear to be all that beholden to the teleprompter.

I wish that the cringiest thing was the rhetoric that he chooses, rather than what he thinks. The thing I learned writing speeches is, especially for presidents, ultimately what you say is going to reflect who you are. That was true of President Obama and it’s also true of Donald Trump. So I do think it’s one reason why speechwriters watch Trump read successfully off a teleprompter one time and none of us say, “Oh, now he’s presidential.” We know better. It’s not just what you do that one time, but the entire body of work that reflects what you’re thinking. It’s not the fact that his speechwriters do or don’t do a good job. It’s that his personality and way of viewing the world comes through, and that’s terrifying whether you’re a speechwriter or not.

You do a lot of demystifying in here about what it’s like to work at the White House: What speechwriters really do, how unglamorous the offices are, and so on. What do you think is the biggest misconception the average person has about your job? 


I think the biggest misconception was that I was Rob Lowe in The West Wing. Before I started working in the White House, I didn’t realize just how much people did, and I didn’t realize the White House is, in many ways, a giant office building. [Really], I was the guy who handed the piece of paper to Rob Lowe and scurried out of the frame.

I wanted to write about what the experience of public service is like for people who aren’t in the inner circle of the president… I’m really proud of my work, but it’s not the same work as someone in the Situation Room the night of the Bin Laden raid. Sometimes, more mundane type of day-to-day work, but it’s also essential if government is going to work.

You describe being panicked and/or terrified just about every time you were in the Oval or spoke with the president. At what point were you not nervous to be speaking to President Obama?

I think by the very end. I don’t know what it says about me, but right around the time I wasn’t nervous speaking to the president was around the time I was like, “well, I think I’m ready to leave.” I don’t write a lot about that in the book, because I thought it was much more fun to write about the times I was terrified to speak to the president. But it was a remarkable moment — I do write about this — a kind of crazy moment when you realize the president knows who you are, and they probably weren’t told by someone right beforehand. It’s nice to at least think that.

“I think the biggest misconception was that I was Rob Lowe in ‘The West Wing’… [Really], I was the guy who handed the piece of paper to Rob Lowe and scurried out of the frame.”

That nervousness that you experienced, how much of that is the office of the presidency and how much of that is who Obama is as an individual?


Let me put it this way: If i was going to meet President Trump tomorrow, I wouldn’t feel nervous. But I’d feel disgusted. A lot of it has to do with the combination [of factors]. I was one of those college kids that fell in love with Barack Obama in 2008, and I was going to go into comedy after I graduated, and then I saw then Senator Obama speak and it completely changed my life. So to meet that person was a sort of overwhelming moment, and to meet that person when that person is also the president and you’re in the White House, there’s a reason I blacked out.

Your book traces the arc from being really all in on the hope of 2008 to seeing the cracks in that vision. 

I wanted to write about the journey from being infatuated to really being in love. And it’s a weird thing to say, but I do feel like I still love Barack Obama. The idea, not the person. I don’t know the person well enough. But when I think about how I felt when I was 21, it was almost this kind of huge crush, but there wasn’t a lot of depth to it. And now when I think about what it means to love a president, another person, or a country, it’s more complicated than that. You love somebody or something even though you know they have flaws, and you believe even though you’re disillusioned. Love is that ability to do both of those things at the same time, in my opinion. To be clear-eyed about someone, and to believe in the best possible version of them, and the best possible version of yourself with them.

You had all these weird niche jobs as a speechwriter, like coming up with snappy comebacks for Obama to have during debates, or writing random birthday and holiday addresses. I think most people forget about that stuff but of course someone has to draft it and Obama is busy doing more important things. What are some of the other non-speech type things you worked on?

There’s a lot of things — especially now in a digital age — that are not speechwriting, but they’re speechwriting-adjacent. Everything from a witty retort in a debate to helping out with a tweet, to trying to negotiate exactly which scenes will end up staying in the Buzzfeed video and which ones get cut. The line between speechwriting and other types of communication is beginning to blur a little bit. It used to be that there was speechwriting and interviews, and that was it. And now with the way politicians communicate, there’s so many different opportunities.

So what percentage of a president’s public comments — in tweets, in speeches, on Facebook — are actually written by the president?

Well, it depends on the president, obviously. A huge amount of President Obama’s rhetoric had its roots in something he originally wrote, whether that’s Dreams from my Father, his convention speech, or edits that would become standard language we would use. So he was reflected in every speech, not just as a president but as a writer, because he’s an excellent writer. I don’t know what it’s exactly like for other presidents. But I will say, we were in the very lucky position where, if President Obama had a lot of edits in your speech, you felt bad — you could’ve done better — but you felt good, because those were the best parts of the speeches.

In the book you talk about the making of that Buzzfeed video. The director, who you affectionately nickname “Man bun,” does… not come out looking great! He gives Obama his business card in case he ever needs a videographer even though the official White House videographer is standing right there. And Obama makes fun of him for that, which as a reader I enjoyed very much. Have you heard anything from Man bun?

I haven’t! To me, that was a story about the way the president noticed people being taken advantage of, and stuck up for people and defended the dignity, not just of his staff, but people who are vulnerable.

You don’t name him, but it seems like it would be fairly easy for anyone to put together who he is, just based on the details you provide.

That is totally possible! I can’t imagine he’s thrilled.

You talk about the White House’s magical way of making people age in hyper-speed, even people who are lower-level staffers. But the White House does not have a monopoly on stress-induction. Why do you think it seems to have that effect on everyone who works there? Is it the public nature of the work, the insane hours, the unpredictability? 

I really got to understand why they used the adjective “crushing” to describe the responsibility. When you feel responsible for even a little piece of something big like that, it weighs on you. And what is nice about my job now is, if I screw up, I’m the only one who is worse off because of it. And when I was in the White House, just like the rest of my colleagues, I knew that if I screwed up, somehow it affected the president and the country, even just in a small way. And having that knowledge all the time and trying to ignore it so you can do your job is exhausting.

“I don’t have any respect for Donald Trump, but I do have a lot of respect for the office of the president. That’s something I try to think about as I try to find my own place in a post-2016 election world.”

What did it feel like to like to leave the White House? 

I left the White House exactly one year before Trump took office. I could still feel all the feelings and it didn’t feel tragic. I wanted to leave the White House before I convinced myself that the country would fall apart without me, because it would have been just fine. The biggest thing was the gradual release of pressure you didn’t even know existed… And the day after i stopped working at the White House, I missed the people I worked with. One of the things I wanted to capture in the book, particularly because it’s so lacking in the current administration, is that in the Obama White House, 95 percent of people are incredible at their jobs.

When I left the White House, someone on senior staff said, “You’ve been working for so long and started when you’re so young, you don’t realize, not everyone out there is good at what they do!” And it’s true. I think working in the Obama White House really spoiled those of us for whom that was our first real job out of college.

Seeing as you’re working now at Funny or Die, can you talk about the role of comedy at this political moment? Because it seems like a lot of people are wrestling with feeling like the stakes are high, and things are so dire, and they feel guilty about not actively contributing every second. Why do jokes matter now?

I certainly feel guilty about not actively contributing every second. It’s good to know I’m not alone. In this particular moment, two different types of comedy are really important. One is the type of comedy that just keeps us sane, and there’s a place for that. If you just really focus intensely on everything that happens the minute it happens these days, you won’t have the energy to keep going. Comedy is a reminder that there’s still good in the world, and there are still things to laugh about.

And the importance of satire has increased because, fundamentally, satire is about truth. The Trump White House does’t just spin the facts; it acts as if the facts don’t exist. And satirists are pushing back on that idea and are asserting facts are still a thing. Reality exists. The truth matters. That shouldn’t be an urgent priority in the United States of America, but here we are.

“The idea that there’s some reshaping of the American character so it reflects Donald Trump instead of Barack Obama, that’s not happening.”

President Obama called you “absentminded” in front of your parents. How often do they bring that up with you? 

It hovers in the background when I do something dumb. People act really weird around President Obama. When I left the White House, you take a departure photo, and President Obama met my parents. He asked, “Who does David get his sense of humor from?” And the accurate answer is, neither of them. And both of them said, “It was me!” So, people get weird when they step into the Oval Office.

It’s good for the Oval Office to be intimidating though, right? Isn’t that part of its function? 

We’re at this moment when it is more important for powerful people to be accessible, because that’s the only way they can get the attention and trust of the people they serve. But there is real value in those symbols. One of the biggest things I think is important right now is, I don’t have any respect for Donald Trump, but I do have a lot of respect for the office of the president. That’s something I try to think about as I try to find my own place in a post-2016 election world.

And one other thing I’d add to that is, for progressives, we’re going to need to figure out a way to get Donald Trump and everything he stands for out of office but still maintain the dignity of the presidency, of Air Force One, of America, so that we have not just our military power but also the symbolic power that America has traditionally had. And I’m worried about what’s happening to the power of America as a symbol, not just practically.

Maybe people in other countries see this as a hostage situation.

To some extent, that’s what protesting and resistance is about. It’s this proof of life. And it’s a reminder that Donald Trump is who he is, but America has nothing to do with that.

So on a scale from “it’s 2008, hope is alive anything is possible!” to “the best we can hope for is climate change will kill us all before we live through the consequences of this administration’s actions,” where are you right now?

The way I always think about it is, I’m a long-term optimist and a short-term realist. So I absolutely think that things are going to get better, and in fact I think that the same movement that’s resisting Trump is going to make America better than it has ever been before. But in the short term, some bad stuff is going to happen, because you have a bunch of white nationalists running the country. And we’re going to have to stay strong even when those bad things do occur.

The thing I keep looking at is, President Trump is doing a lot of awful stuff but it makes me hopeful that Americans recognize that, and a clear majority of Americans — not just Democrats — don’t like it. It’s true he has a lot of power; he’s the president. But the idea that there’s some reshaping of the American character so it reflects Donald Trump instead of Barack Obama, that’s not happening. And that’s why I’m optimistic in the long run.