Talking Comedy and Politics with Former Obama Speechwriter David Litt

Not many people can claim that they landed their first post-college job as a 24-year-old speechwriter and joke writer for the President of the United States, which is just part of what makes David Litt’s new book Thanks, Obama: My Hopey, Changey White House Yearsout today, so fascinating. Now head writer at Funny or Die’s new DC office, Litt describes his former White House role as “not that important” compared to some of the more well-known staffers and speechwriters, but for any comedy/politics nerd, Litt’s unique job helping craft jokes for Obama’s speeches and annual White House Correspondents’ Dinner performances – not to mention collaborating with the Funny or Die team for Obama’s smash hit Between Two Ferns episode – is nothing short of a dream job. I recently spoke with Litt about why he decided to write a book about his White House years, what it’s like to get joke edits from President Obama, and how, when it comes to our current president giving big speeches or unscripted tirades, “the truth tends to find a way out.”

Congrats on the book, I really enjoyed it. It was weird – it’s like taking a break from all the news, but at the same time, it’s still very connected to the news too.

Well thanks! I really appreciate that. And it’s funny – I started writing the book when I was sure, like everyone, that Hillary was going to be president, and so that was not originally how I thought about it. But then after Trump won, I realized there’s this other element to a book like this, where it’s sort of like time travel a little bit.

I know you mention in the book that you were writing parts of it right around Trump’s inauguration, but when did the whole thing get started?

It sort of started with the fact that I had these funny embarrassing stories I would tell to friends when they wanted to know about my job, and then gradually realizing that I wanted to share them. Originally I was going to do a one-man show, and I talked to someone who was like, “You’re a writer – you should write a book!” And I was like “Well, that makes sense.” So that’s where the idea came from, and I actually started writing the book around Valentine’s Day of 2016.

And that was right after you left the White House, right?

Yeah. I left knowing that I wanted to try to write a book about what it was like to be not that important at the White House, because there’s lots of really good White House books, but most of them are by people who were in the real inner circle, and I was definitely not. I thought there was something kind of fun and different about that experience, and because I had a writing background, I could write about what it’s like to have a White House job be your first serious job out of college.

What was the hardest part of putting the book together and figuring out how to tell your story?

The hardest part was I had experience writing in two different ways: I’d written speeches and I’d written jokes. At first I was like “Oh, how hard can this be? Just take 20 speeches, string them together, and you have a book.” And then I discovered that is totally not how that works. It was also really tricky, because you get so used to writing in someone else’s voice and you stop asking yourself “What do I sound like?” That was part of the exciting thing about the book – I wanted to know what I sounded like as a writer. But then you realize that nobody’s there to tell you you can’t do something, which is great, but also, there’s no one there to tell you what to do, and that turned out to be way scarier than I realized. The book started with a lot of setup-punchline jokes because that’s a kind of writing I had done a lot of in the White House. It took me a while. I sent it to comedy writer friends, and very politely they were like “This is good, but maybe you don’t need to be so jokey” and to just let the stories speak for themselves, and I think having that kind of confidence – it took a while to get there.

What got you interested in politics before working in the White House when you had campaign jobs?

Let me put it this way: If you had the kind of skills I had as a history major coming out of college – which is to say, not a ton of them – you end up working in field, usually, as your first campaign job, because it doesn’t require any specialized expert knowledge. So that’s kind of the rite of passage for a lot of political people, because that’s where you go when you don’t have something you’re really good at. I ended up discovering that I liked it, which was sort of really lucky. In some ways it was great training for writing speeches – even for writing jokes, because when you’re asking someone for their time, if you don’t have a sense of audience and a sense of what they’re going to respond to and what they’re not, you’re totally hopeless. So that sense of being able to listen to people but also ask them for stuff or have a reaction you want to get out of them turned out to be really good training for my next job working for President Obama, but I didn’t know that at the time.

Slightly off topic, but I have to ask: Have you heard about that AI that can create videos of Obama giving fake speeches? I’d love to hear a presidential speechwriter’s thoughts on that.

It’s totally scary. I think all of us just need to become not cynics but skeptics about all of these things we used to take for granted, because the old days when you had a lot of top-down arbiters of what’s important and not – it’s harder than ever now to figure that stuff out. So a lot of it depends on the fact that you have to make a decision, as a consumer of news, who to trust. And you can’t just trust people because you agree with them – you have to trust them because they have some commitment to the truth. But this is the other thing: I feel like most young people see a random video on Facebook, and their first assumption is that it isn’t true and they look into it. The scary thing is things change so fast that it’s like, yeah, everyone’s got that uncle who’s like “Well, it’s on Facebook, so it’s gotta be real.” So I’m not worried about the next generation. I’m a little worried about the generation that just assumes that because it’s on the internet it must be true.

The Daily Show did a segment on Trump’s Afghanistan speech where they showed how several parts of it were almost directly lifted from Obama speeches. Is that a trend you see sometimes in Trump? I remember reading Stephen Miller is one of his speechwriters – I’m not sure who else is.

I’m not sure. I know they downsized the speechwriters considerably, which will probably come as no surprise. It’s not like, looking through speeches, there’s all these moments where you’re like “Oh that’s outright plagiarism,” but I do think, in this weird kind of flattery that I don’t think any of us would really like, you get the sense that somebody is at least googling and reading up on what Obama had to say about it to find out what a real adult sounded like.

[laughs] That’s a good way to put it.

They would never admit it, but clearly someone’s sitting there being like “Uhh, what does an actual president sound like?”

You say speechwriters are like “personal trainers” in the book and that they can “help you present the most attractive version of yourself to the public” but “they can’t turn you into someone you’re not.” In that way, it seems like an extinct, or at least hopeless job in the Trump administration. 

First of all, I don’t think it’s a hopeless job, because you can always quit. I don’t feel sorry for anybody toiling in the Trump administration. No one’s forcing you to do it, you can resign – and should, at this point. When I started as a speechwriter, people would ask, “Can you put words in someone’s mouth?” And one of the things that was comforting to learn about speechwriting was that that’s not possible. And you can see this with Trump, right? They can write some stuff on a prompter, and sometimes he’s able to read words in the order they’re written without doing anything insane, but invariably, the next night, he just totally goes and loses it and almost punishes everyone around him for trying to control him by being even more outrageous and awful than he would have been if they hadn’t made him stick to the script the day before. With rare exceptions, the truth tends to find a way out.

As someone who knows how things work behind the scenes at the White House, what advice do you have for those of us on the outside in terms of resisting Trump?

The advice I would have is we have to be able to totally reject this president without rejecting the democratic institutions that brought us here. We can fix those things, and I think for now we have the tools to, as long as we don’t walk away from the whole thing entirely. So to me, practically speaking, what that means is yes, think about the crazy thing that Trump said and make fun of him because he deserves it, but also go volunteer on a campaign in 2018, donate to a candidate you believe in even if it’s just a couple of bucks, do the things that represent politics at their best. I think that we’re in real trouble as a country right now, but it’s not a hole that’s so deep that we can’t get out of it if we all work together.

You talk about some of the uncredited joke writers who helped out like Katie Rich, Andrew Law, Judd Apatow. How do you get that gig? Do you just gotta know someone who knows someone?

[laughs] One of the nice things about working in the White House was I could email or call any number of my comedy heroes and they were usually really eager to return a phone call, and that was really nice, just as somebody who grew up a total comedy nerd. I mean, I read Splitsider. Let me put it this way: I was probably the only person on the White House staff for most of those years who was reading Splitsider in addition to all the political news. So it was just fun to be able to talk to people like that. Sometimes they pitched jokes for us, and sometimes they just told us how they thought about telling stories. Tig Notaro was in town for a show once, and she was gracious enough to stop by the White House and talk about storytelling with the White House speechwriters, and that was an amazing experience. And to answer your question a little more directly, it’s the same way I think anybody gets into politics or even a comedy writing gig. It wasn’t like we had a writing packet, but it was some combination of you reaching out to the people you know and trust, the people whose work you admire, and people who have perspectives that aren’t identical to yours. The nice thing about having people who wrote comedy full-time was that their style of writing jokes was different depending on the writer and also totally different than people who write speeches.

How is writing a Correspondents’ Dinner joke different than writing any other kind of joke?

So the way that we did the Correspondents’ Dinner, the majority of those jokes tended to be written by Obama speechwriters, but we’d also work with outside writers for jokes as well. That’s partly because writing a joke for a president is so different than writing a joke for anybody else. When you’re writing a joke for the president, most of the joke or a lot of the joke is it’s the president telling a joke, so it’s just a very specific style, and you also have to know where the lines are so that you’re walking right up to them and not crossing them. Most joke writers don’t have to wonder, like, “Will this joke get covered by Fox News?” That was something that we did have to think about. And you have to think about what happens if there’s a national tragedy the day after the Correspondents’ Dinner – is this joke going to look insensitive in retrospect? Comedy is all about not censoring yourself, but politics is all about censoring yourself, so it’s all about trying to balance those two things.

There’s a point in the book where you mention Obama gave you a note about a Dick Cheney joke and he wanted it to be edgier. That was a nice insight.

I will say, I had the luckiest presidential joke writing gig that has ever existed, because President Obama is A, really funny and has good timing, and also B, just has a good sense of humor. So he was always the one pushing us: “Can you make this sharper? Can you make this edgier?” And he had just a really good sense for exactly how far he could go, where it was going a little farther than we did the year before but never crossing that line into something that would be truly inappropriate. I also think that he liked to make fun of himself, but he also, I think, enjoyed the way that you can use comedy to make a point that you don’t always get to make when you’re the president, because it gets bogged down in politics. So when he was joking about Mitch McConnell or the Koch brothers, you can do that in a way where if he’d just said that in his speech it would’ve seemed out of place, but in the middle of a run of jokes, it works.

My mom always quotes the part of Obama’s Between Two Ferns episode where he says to Zach Galifianakis, about Michelle, “I’m not gonna let her near you.”

I was like the boring policy person on Between Two Ferns. That was all Scott and Zach and B.J. Porter and the whole Funny or Die team. Obviously I work for Funny or Die now, but then I was on the other side. So I can’t take any credit for that, but one of the things about the president was he’s just good at banter, and that came across in a lot of Dinners. I didn’t write about this in the book, but there was a joke about Cliven Bundy, the Nevada rancher who had this whole standoff with the federal government, then it turned out he said some racist stuff. President Obama improvised a whole riff on that, and that’s not something a whole lot of people can do, let alone presidents. And it was really good! So every year we would talk to the comedians and their team who were doing the hosting, and they were basically like “If he ever wanted to go into comedy, he has a real future here.” [laughs]

It seems like speechwriting is great preparation for a comedy writing career, since it gets you so used to writing for different people’s voices the way you would for a late night host or characters on a show.

The interesting thing is, to some extent, speechwriting is a little bit like parody writing. Like, if you wrote a parody of a speech for a politician, and then you dialed back the exaggeration by 20%, you have a speech for a politician. It’s not like I would sit in my office doing an “Obama voice” or something like that, but you do have to recognize patterns, and you have to think about what is identifiable and unique about this person and their persona in the same way you would if you were either parodying them or if you were writing for them on a show.

Given that, is there anyone who you haven’t worked with that you’d love to write a speech for?

I mean, the answer is clearly yes, but I can’t think of any examples at the moment. I will say this: One of the reasons I don’t write a lot of speeches these days is that I feel like, all due respect to all other people in the world, but I am just not going to get a speechwriting job that’s as good as the one that I had. It’s never gonna happen. It was one of those things where I was, in a variety of ways, so incredibly lucky. And when it comes to outside writers and stuff like that, I ran the process for a couple of years, but the difference is that compared to writing speeches, joke writing is really a team effort. So you don’t have a writers’ room for a eulogy, but you do have a writers’ room, or a virtual equivalent to one, for a Correspondents’ Dinner, where different people are pitching ideas and you might take a joke and beat it and make it better.

The other difference about writing jokes is that it’s so binary. If you write an applause line for a president and it gets a B+ instead of an A+, then it’s fine – it’s not ideal, but it’s fine. If you write a joke and it’s a B+ rather than an A+, then that joke totally bombed. It either works or it doesn’t. So because of that, on a typical messaging speech, President Obama wouldn’t need to meet with us and go over it, but with the Correspondents’ Dinner we always went over it a couple of times because he understood that the timing has to be really good. Every night during the Dinner during the years that I was kind of taking the lead on it, I would get his handwritten edits from that day, and I was always impressed. Like, he’d move a comma from point A to point B, or change the word “actually” to the word “really” – these little, small tweaks that really did make stuff funnier. It’s one of those things where, just as a writer, you’re like “Not only is this guy the president, but also, he’s a better writer than his joke writers.” So that was a pretty humbling experience.

How’s the DC branch of Funny or Die going?

It’s great. The political comedy market is kind of countercyclical. When things are going great for America, political comedy is probably harder, so I guess it says something about where we are as a country that political comedy is doing great. But I also think we’re trying something that is a little unique, which is figuring out how to use comedy and work with some of the best in the industry to have a real measurable impact. There’s lots of ways that comedy can be a force for good, but we’re more direct about exactly the kind of change we hope to make. And so far it’s been great.

Is the focus purely politics? How does the DC office fit in with Funny or Die as a whole?

Well, we don’t do everything that involves politics, but everything we do involves politics, if that makes sense. I think it’s part of a broader sense in Funny or Die – I think our CEO Mike Farah was pretty early to this – realizing that the barrier between comedy and political advocacy is falling just like it did with Between Two Ferns, and it makes sense if you’re a comedy company to have a presence in DC, whereas ten years ago that wouldn’t have made a lot of sense.

Maybe you can get Obama to do a Funny or Die web series…when he gets some free time.

[laughs] My guess is he has a lot of offers right now. But I think it’s fair to say that doing Between Two Ferns with him was certainly a highlight for everyone at Funny or Die. It was pretty fun to get to be a very very small part of stuff like that.

You referred to yourself as “not that important at the White House” earlier, but as an outsider, I don’t know. Seems pretty important that you got to be part of the president’s voice. 

I think that’s right. And that’s part of what I wanted to do with the book too – write about how the White House is a special place, but it’s also an office building, and there are thousands of people who are each doing their little part to make the thing work the way it’s supposed to. That’s something that maybe we took for granted ten months ago, but I don’t think we take that for granted anymore.

Is Sarah Palin still in your head?

Uh, every so often, but I think she’s been replaced with the much louder, even less pleasant voice of Donald Trump.

You’re not alone.

I know. It’s a sad day when you’re wishing that all we had do deal with was Sarah Palin. Back in the good old days.

Litt’s book Thanks, Obama: My Hopey, Changey White House Years is out today.

Talking Comedy and Politics with Former Obama […]