A Former Speechwriter Looks Back On His 'Hopey, Changey' Years With Obama

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. My guest, David Litt, wrote jokes for President Obama, like this one.

(SOUNDBITE OF ARCHIVED RECORDING)

44TH US PRES BARACK OBAMA: A few weeks ago, Dick Cheney says he thinks I'm the worst president of his lifetime, which is interesting because I think Dick Cheney is the worst president of my lifetime.

GROSS: That was President Obama doing stand-up at the 2015 White House Correspondents' dinner, one of the four White House Correspondents' dinners for which David Litt served as Obama's lead writer. After he started out in 2011 as the guy on the speechwriting team who was assigned the speeches no one else wanted to write, Litt became a special assistant to the president and senior presidential speechwriter. He's written a new memoir called "Thanks, Obama: My Hopey, Changey White House Years."

Before writing speeches, Litt wrote for the satirical newspaper The Onion. While he was still in college, he worked as a volunteer on Obama's first presidential campaign. Litt is now the head writer-producer at Funny Or Die's Washington, D.C., office.

David Litt, welcome to FRESH AIR. Since you worked on several of the White House Correspondents' dinners and since Obama was always so funny at those dinners, let's start there. First of all, tell us a couple of your best jokes that you wrote for Obama at the White House Correspondents' dinner.

DAVID LITT: Well, for me, my favorite jokes were always not just the ones that were funny but also the ones that he personally enjoyed. So one I write about is the 2013 dinner. He - this was an earlier time when Republicans felt that they needed to do a better job of reaching beyond their base. And President Obama said, one thing all Republicans can agree on is they need to do a better job reaching out to minorities. Call me self-centered, but I can think of one minority they could start with.

And I love that joke because it is - it was the first time, to my knowledge, President Obama ever referred to himself as a minority in public. So it was an example of where we got to go a little farther with the jokes or a little further with the jokes than you could otherwise go. And it was also just one that he enjoyed a lot.

I mean, it - I could always tell, if he really liked a joke, he'd add his own spin on it. He'd sort of tag it. And with that joke, he said, you know, that's pretty good. I might add a little wave in there, like a hello. And the - in the actual performance, he also added the line, think of me as a trial run, which I thought was pretty funny. So ones that - ones where he personally got invested in it, those were always my favorites.

GROSS: Why wouldn't he have referred to himself as a minority before agreeing to do that joke?

LITT: Well, this was the beginning of the second term, and in the first term, I think there was still concern about exactly how far we wanted to go. I mean, everybody knew that President Obama was the first African-American president. He had already spoken many, many times very eloquently about race, but him publicly identifying himself in that way was still something that prior to the 2012 election we would've been skittish about, I think, in a joke.

As an example, in the 2012 election, we had thought about asking Keegan-Michael Key to come on as Luther the anger translator because President Obama was a big fan of "Key And Peele." I think the show had just started then and I remember there was sort of a general sense of that would be really funny, but do we really want to suggest that President Obama is secretly an angry black man - probably not.

GROSS: So let me ask you to explain for people who never saw this "Key And Peele" sketch and never saw Obama's White House Correspondents' Dinner take-off on it, who is Luther, Obama's anger translator?

LITT: So Luther the anger translator was a character that Keegan-Michael Key and Jordan Peele, from their Comedy Central show, came up with their writers. And the idea was that Jordan Peele would play the president, and he would be very composed and calm, and - both about race but also about all of the other elements, all this other craziness that people put Obama through. And Keegan-Michael Key would be his translator because President Obama couldn't show anger in his actual life so he would be there to rant and rave about whatever Obama was really thinking.

And, perhaps unsurprisingly, President Obama liked this character a lot. And that year we had thought about it. And we thought about it every year until 2015, when we could finally do it. It was one of those things where we always imagined, wouldn't it be fun to have President Obama as the President Obama character and have Luther the anger translator there with him to translate? But it never felt quite right for a variety of reasons. And then in 2015, to me, it was the thing that was indicative of this shift in tone that we had after the midterms. We all said, oh, yeah, this makes total sense.

GROSS: Why don't we hear an excerpt of how that sounded? So this is the "Luther, Obama's Anger Translator" sketch at the White House Correspondents' dinner.

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OBAMA: You know, I often joke about tensions between me and the press, but honestly, what they say doesn't bother me. I understand we've got an adversarial system. I'm a mellow sort of guy. And that's why I invited Luther, my anger translator, to join me here tonight.

(APPLAUSE)

KEEGAN-MICHAEL KEY: (As Luther) Hold on to your lily-white butts.

(LAUGHTER)

OBAMA: In our fast-changing world, traditions like the White House Correspondents' dinner are important.

KEY: (As Luther) I mean, really, what is this dinner?

(LAUGHTER)

KEY: (As Luther) And why am I required to come to it? Jeb Bush, did you really want to do this?

(LAUGHTER)

OBAMA: Because despite our differences, we count on the press to shed light on the most important issues of the day.

KEY: (As Luther, yelling) And we can count on Fox News to terrify old white people with some nonsense.

(LAUGHTER)

KEY: (As Luther, yelling) Sharia law is coming to Cleveland. Run for the damn hills.

(LAUGHTER)

GROSS: So that was President Obama at the White House Correspondents' dinner with Luther, his anger translator, played by Keegan-Michael Key. And my guest is David Litt, who wrote jokes for President Obama and was one of his speech writers, and now has a memoir called "Thanks, Obama."

And one more joke I want you to tell before we move on...

LITT: Sure.

GROSS: And this is the Sarah Palin pit bull joke.

LITT: Yes, and I should say, one of the things that I learned about writing jokes for a president is that some of the joke is always that it's the president telling a joke. And so as I retell them, I am - I often am reminded of this because people kind of give me a look like, really? That was funny? And I'm like, well, you have to hear the president tell it. But I will tell the - this pit bull joke.

So this is hard to believe now, but in 2012 in the spring, there were two very big dog-related stories in the political news that were actually being taken seriously. The first was that Mitt Romney had gone on vacation with his family, and instead of putting the dog in the car, he had put it in a crate strapped to the roof. And the second story - because the Romney people realized this was a liability, they pulled up an excerpt from President Obama's autobiography where he said, when he was 6 years old growing up in Indonesia, he had eaten dog meat. And so there was this question - is it worse to have put a dog on your car as an adult, or is it worse to have eaten a dog as a child? And this was actually something being taken seriously by the political press.

And so the joke that I wrote was about - Sarah Palin had just been on the "Today" show. She was guest hosting. And President Obama said, Sarah Palin's back in the news. That reminds me of the old line she used. What's the difference between a hockey mom and a pit bull? A pit bull is delicious. And I remember we had some conversation about whether we should even show the president that joke and whether we should use a joke that - where eating dogs was part of the punchline. But he loved it. He thought that one was really funny. And that was another one where he added his own sort of spin on it. And he said, well, you know, that's - I like that. Maybe I'll add - you know, put a little soy sauce on that. And he did kind of a sprinkling motion in the actual room - adding some seasoning. And so it was always fun when you got the sense that he didn't just feel like the joke was going to be good, but he actually, really - he really laughed at it himself and really enjoyed it.

GROSS: And that was also a kind of self-deprecating joke in some ways.

LITT: Exactly. It was a way to both make fun of himself and also make fun of the idea that all of this was a serious question in a presidential election. I mean, honestly, would it really have made a difference for either candidate? Mitt Romney - the kind of president he would've been would not have been informed by the vacation he took with Seamus the dog. And it also wouldn't have been informed by the, you know, snack that 6-year-old Barack Obama had when he was a kid in Indonesia. But that was how the political press was viewing it at the time. So it was a chance to comment on just how silly some of that was.

GROSS: You know, the White House Correspondents Dinners basically have become roasts, and the jokes are pretty cutting. So was there, like, a ground rule for how cutting a joke could be and when did it cross the line to actually be - to go too far, to be to offensive to the person who was being satirized?

LITT: I think the jokes that President Obama told - and it's not like there was a memo written. But there was just a sense of who the president is and what he would feel comfortable with. The jokes were always trying to make sure that we were getting at some truth that was important - and also, if we were kind of targeting someone with a joke, that it was someone who deserved it and in a way that they deserved it. I mean, every year we would get pitched jokes, and this was totally fine. It's everyone's job to pitch everything that they think of.

But you'd get jokes making fun of, let's say, you know, Chris Christie's size. And we never would use that in a speech because that's not the thing about Governor Chris Christie that is worthy of mockery. And that sort of thing where we would make sure that it was about the political, not about the personal, I think was important. I will say that President Obama was often the one pushing us to - his words were, you know, can we make the sharper? Can we make this edgier?

GROSS: So what was the process of running jokes past him once you had written them or gathered them from the other writers who were writing comedy for him?

LITT: Usually, about a week before the dinner, we would bring in a list of about 40 jokes. And this would be called from, usually, about 600 submissions. I mean, we'd get tons of jokes. We'd only bring the ones that we thought were absolutely the best to the president. And we'd sit on the couches in the Oval Office. And he would read through the jokes, and he'd read them out loud because with jokes, as opposed to other speeches, you kind of - you can't skim them. You have to hear them.

So he would read them out loud. And I would always be sitting there kind of with my heart in my throat hoping that he liked everything, knowing that he wasn't going to like all of it. But there's always a few jokes that you really are excited about in that list. And I would be listening to him and hoping that those would be the ones he'd really respond to.

And then often, he would make small suggestions to a joke. He didn't usually rewrite something from scratch. But he would say, oh, this is good, but, you know, maybe we sharpen it up. Maybe we figure out a way to go at this a little bit differently. So he might say, I like that topic. But that joke isn't doing it for me.

GROSS: Well, I'll tell you what, let's take a short break here and then we'll come right back and talk some more. If you're just joining us my guest is David Litt. His new memoir "Thanks Obama" is a memoir about his years writing speeches for President Obama and writing comedy for him for the White House Correspondents Dinner. We'll be back after a break. This is FRESH AIR.

(SOUNDBITE OF NAOMI MOON SIEGEL SONG, "IT'S NOT SAFE")

GROSS: This is FRESH AIR. And if you're just joining us, my guest is David Litt. From 2011 to 2016, he wrote speeches for President Obama. He came to specialize in writing jokes for Obama and became his senior presidential speechwriter. He's written a new memoir called "Thanks Obama." And he's also now the head writer and producer for Funny or Die in Washington D.C., so in the Washington D.C. branch. So what was your reaction when President Trump declined to attend the White House Correspondents Dinner this year.

LITT: I was not surprised that he didn't go because I had watched him at the Al Smith Dinner, which is kind of the correspondents dinner of the presidential campaign. And he got booed during that dinner. And it is more or less impossible to get booed during a dinner like that. I mean, politeness is kind of the core virtue of a society like the Al Smith dinner. And he still managed to do it.

So I think he understood that it wasn't going to go well if he came. He just - he does not have the ability to deliver the kind of jokes that presidents are supposed to and that people appreciate from their presidents. I was still disappointed that he didn't give it a shot and that he didn't try to sort of meet the standard that has been set, not in terms of comedy but just in terms of self-deprecation, in terms of acknowledging that you're only human.

You may be the president of the United States, but you're also just a person. And you have flaws, and you make mistakes. And there's a way of using those jokes to acknowledge them through comedy. And I think that is an important democratic tradition in its own way. And I wish that President Trump realized that, and he was willing to participate in it. I'm sadly not surprised he was not.

GROSS: So when you started writing for President Obama, you were basically just out of college - I mean, a year or two out of college maybe?

LITT: Yeah. I was about two years out of college, maybe three. I graduated in 2008, and I started writing at the White House in 2011.

GROSS: What did it feel like to be that young and inexperienced and putting - trying to put words in the mouth of the president of the United States?

LITT: It felt totally surreal and completely terrifying. And that's one of the things that I wanted to let people know. Because when I imagined a White House job, I figured you'd walk through the gates and suddenly you're a White House staffer. You must be completely perfect and flawless at what you're doing. And then I walked through the gates for the first time and realized I was not any better than I was 15 seconds ago when they let me in. And I wanted to be honest about that. I wanted to be honest about how scary it can be. And it's wonderful and amazing but also totally terrifying.

I remember the first time I met the president. He asked me a question, and I literally blacked out. I don't know what I said to him because I was so afraid to meet this person who had had such an impact on my life already and also, by the way, was the president of the United States.

GROSS: The question was, how's it going? I mean, it wasn't...

(LAUGHTER)

GROSS: It wasn't a hard question (laughter).

LITT: It was a hard question at the time.

GROSS: It's the kind of question where you're supposed to say, fine. Thank you.

LITT: And it's totally possible I did. I couldn't tell you. I don't remember. And that's - I actually think that, in a nutshell, is so much of the White House, that - I would agree with you. Most of the time, I am very capable of answering the question, how's it going? If that's your next question for me, I will do a great job.

GROSS: (Laughter).

LITT: But at the White House, there's a level of pressure, and you know that the stakes are high in every little thing. And that knowledge, even if it's not in the front of your mind - it infects everything that you do. And so suddenly, it's the president of the United States, and he's looking at me. And he says, how's it going, David? And I remember I had exactly one thought in that moment, which was, I did not realize we were going to have to answer questions. And I have no idea what I said.

And I think that ability to function normally under intense pressure, that's actually the hardest part of a White House job. It's not being brilliant all the time. It's being competent even though there's all these incredibly difficult, high-stakes things happening around you.

GROSS: So when you're writing speeches for President Obama or writing jokes for him, it's not just a question of how the president is going to react, it's also a question of how the world is going to react and how the press is going to react. So I'd like to ask you to give an example of something pretty minor, really, but that ended up getting criticized. And this was - I think it was your, like, your very first speech that you wrote for the president. It was a Thanksgiving Day speech. So tell us the story of that. And by the way, did you have to pardon a turkey in this speech? Is it one of those?

LITT: No. I, somewhat shockingly, managed to never do the turkey pardon. And I don't know how I managed to avoid that one. No, the turkey-pardon speech was always - that was sort of the most pun-laden speech of the year because there's all these Thanksgiving puns. So in some ways, it was fun. And in some ways - every way - it was sort of, by definition, it was sort of the - a festival of dad jokes.

But this was 2011. I was writing the Thanksgiving video address, which is not the most important presidential speech, not by a long shot. But it was my first video that I'd ever written for President Obama. And I treated this thing tremendously seriously. And I thought I had done it. I thought I had done the perfect job of capturing the spirit of Thanksgiving for America. And the problem was that I left out the word God or the Almighty.

And I will say, in my defense, at one point during the video, President Obama talked about giving thanks for blessings. So it's not like he was - you know, these blessings were coming from somewhere. It's not like we hadn't mentioned the idea of the Almighty at all. But this was enough for Fox News to jump on it and start a controversy. And by the time dessert was served, I was with my family, and I remember, you know, everyone was excited for me when we started the meal. And then by the end, it was clear this was going to be a story because Fox ran a Obama-leaves-God-out-of-Thanksgiving-address story.

The conservative media began to pick it up. And then the mainstream press - I use ABC News as an example - they didn't cover the omission of the Almighty in the speech because I think they would've agreed that was not a big deal, but they did cover the controversy. So they ran a separate story about the fact that Fox News had run a story and that conservatives were riled up about this issue. And so you watched as this thing, which wasn't really a story at all, but it was a very small omission - it gradually seeped into the news cycle. And I say that not because I am avoiding responsibility for it.

One of the things I learned as a White House speechwriter is that your job as a speechwriter is not to just write good speeches. Your job is to keep in the back of your mind the fact that there's a whole industry of people trying to take your words out of context. And that's politics. And so you need to write something that - where you read through it and you say, A, are we saying what we want to say? And B, can this, under no circumstances, be misconstrued to say something different? And those kind of dual responsibilities are one of the reasons writing for a president is so difficult.

GROSS: Isn't Thanksgiving a secular holiday?

LITT: (Laughter) Not according to Fox News, it's not. It is true that George W. Bush left God and the Almighty out of, I think, five of his eight Thanksgiving Day addresses. "The Daily Show" did a whole piece on this. But it was one of those ways that I think the rules were different for President Obama than they were for his predecessor or than they are for Donald Trump when it came to the right-wing press and the way it - to some extent, the mainstream press, too. He was held to a different standard. And you can complain about that. We certainly did. I certainly did. But you also recognize that's reality, and you have to meet that standard even though it's not fair.

GROSS: My guest is David Litt. His memoir is called "Thanks, Obama." We'll talk more about writing speeches and jokes for President Obama after we take a short break. And Ken Tucker will review two new albums by the band Deer Tick. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF SEAN JONES QUARTET'S "I DON'T GIVE A DAMN BLUES")

GROSS: This is FRESH AIR. I'm Terry Gross back with David Litt. He's written a new memoir about writing speeches for President Obama. It's called "Thanks, Obama." He was only 24 when he started writing for Obama. He became a special assistant to the president and senior presidential speechwriter. He's now the head of - he's now the head writer for Funny Or Die's Washington, D.C., office.

I always thought that there was a kind of code of silence that speechwriters for the president were supposed to have to make it seem as if, nope, the president writes all the speeches by himself. We're there to edit it, but it's his words. But now speechwriters write memoirs, so that code of silence has been broken. I mean, am I right in assuming that the code has changed over time?

LITT: Yes. It's definitely changed. I - there's an anecdote that's very popular in the speechwriter world. I think it was Ed Muskie, the senator from Maine in the '60s or '70s. He used to go up, take out remarks on paper and say, here's the draft my speechwriters have written. And then he would tear it in half and say, but I'm not going to use that. And then he would deliver the exact same speech...

GROSS: (Laughter).

LITT: ...From memory that he just tore in half. And there used to be a very sort of, almost a macho sense of, well, I don't need speechwriters. I'm going to do it all myself. I think that that has clearly changed, in part because nobody questions whether President Obama is a talented writer. He wrote a fantastic book well before he ran for office. And I think one of the things that I and other former White House speechwriters for President Obama have talked about is the way that he would be very personally involved in big speeches.

But also the president speaks so much more than presidents used to. I forget the exact number, but I believe it came out to more than once a day. So the idea that a president could possibly be writing not just the State of the Union but every policy address, every weekly address summary, every little video that is going to be played at a conference somewhere - they would never have time to do anything else. So I think we've just gradually realized that we don't want presidents who couldn't write speeches if they had the time. But presidents don't have the time, and that's OK.

GROSS: So say you've written a speech on overtime or infrastructure that the president has to deliver. How soon - how far in advance does he actually see the speech?

LITT: We would usually give a speech like that to the president just the night before because those would be issues he's already addressed. And there's language we would already have. With a big speech...

GROSS: Language you had because he told you, here's what I want to say, here's my talking points, write a speech?

LITT: Well, one of the interesting things about writing for a president is everything the president has ever said is transcribed. So when we're doing a speech about infrastructure, for example, I could look back at the last five speeches about infrastructure and say, OK. This is the thing - this is the paragraph that has been the same in all five speeches. Probably, it should be in the sixth one as well. And then I would be trying to figure out what is different and special about this one. How can I add something about the location or the new policy we're announcing or tell a story of a person in the audience that hasn't been told before?

But those were add-ons. They were sort of decoration rather than architecture of the speech. And President Obama would make edits to that. But generally speaking, he understood that these speeches are not ending up in the history books. He's got other things to do that were well more important. And so he would make small changes, but often, especially in the second term, he would just adlib something if he thought he had a better way of putting it.

In the first term, because there's the danger of people taking your words out of context and putting them in a campaign ad, we were even more careful about making sure that what was written on the page was exactly precisely right. In the second term, he was a little more willing to edit on the fly.

GROSS: One of the things that you did was write zingers for debates. So how is that worked in? Like, you just right out-of-context zingers to be used as needed (laughter) during the debate, yeah?

LITT: Pretty much. It's - there's not a science to it. But the best you can do is say, well, probably, our opponent's going to say this. And if they say this, we can say that. Or this is a way of encapsulating a political argument in one line. And so we're going to make sure that we figure out a way for our candidate to drop that in there somehow.

So the zinger that I wrote in 2012 that I was very proud of was about Governor Romney's plans. And President Obama was going to say, Governor Romney refuses to release any details about any of what his plans would actually do. Do we think that's because the details are just too good? And that was the kind of little sarcastic line that, again, for a president is pretty edgy. It would ideally make the news the next day.

And those kind of zingers you'd think about how you sprinkle through a debate. I will say in the end, debates, like many things in politics, are harder to control than we would like to think. And so a lot of what political operatives do is do lots of work to create the illusion of control. And then as we discovered in that 2012 debate, sometimes you just can't make things go the way you want them to.

GROSS: So did the president use that zinger in the debate?

LITT: He did. But that was the debate with Mitt Romney that really did not go well. I mean, from the very first moment, it was clear that we were not going to win this debate, not on policy grounds but just on who was better television. Mitt Romney was charming and warm. And President Obama looked like he didn't really want to be there. And he used my zinger about 70 minutes in, and it did not zing. It completely did not zing.

I remember watching it and just thinking, oh, dear. Like this is - not just that line, but that was the one thing I had been looking forward to at that point in a debate I knew was not going well. And after that, I think that's the point when I just turned off the live stream in my office and said, OK. I can't watch the rest of this.

GROSS: You thought the president just wasn't on his game that night.

LITT: Right. The thing about Barack Obama is, this is the best political performer of his generation. There's no question about it. And I had benefited from that many, many times. I would write something that was just OK, and he would make it sound terrific. But I also think what's interesting about President Obama is despite being very, very good at political theater when he wanted to, he didn't enjoy political theater. And this was a moment when - because debates are not really about who has the better vision for the country, they're about who looks better on TV - you could see that disdain for the ritual of the debate, for the theater of the debate come through.

But voters watched that, and it looked detached. It looked like he didn't really care about what was going on, and he didn't have the passion that they associated with President Obama from the 2008 campaign and from so many other moments in his presidency. And so this was just one of those moments when, despite his gifts as a political performer, none of them were evident on that particular night.

GROSS: Did you write any of the tragedy speeches - for example, the kind of speech the president would give after a mass shooting?

LITT: I'm trying to think, actually. No, the closest I came - so on the sort of White House - the tiers of White House speeches I think, a speech like the State of the Union was probably the most significant. Big national tragedies really are the second most significant speech. And those were the two that I never really did because by the time I left, I was sort of the third speechwriter on the totem pole. The closest I did - I did one speech on a anniversary of 9/11. And I believe it was the 11th anniversary of 9/11 or something like that. So every so often, you did write eulogies or pieces along those lines. But I didn't do any of the big mass-shooting speeches.

GROSS: What do you think so far of President Trump's speeches? And I'll include in this his inaugural address, with the most famous line from the address being, this American carnage.

LITT: OK (laughter). Man, sorry, there's just so much to unpack with President Trump speaking. When I think about President Trump's speeches, I honestly wish that my biggest concern was the rhetoric or the words that he's using. And it's impossible to get past the thoughts that he's conveying and the argument that he's making. And the line that you just used about American carnage is a perfect example. It seems to me that that's a departure from all previous presidents who have tried to be optimistic, who have tried to say, this is the best of what America can be.

And Donald Trump, because of his style as a candidate, he needs you to believe that America is falling apart because his argument is, I alone can fix it. And so at every moment, he is saying these things that are not at all in keeping of what we would think of as presidential. They're trying to make America seem worse than it actually is, rather than make us realize that America could be better than it's ever been before. And so it's not a speechwriting concern. It's not a matter of rhetoric. It's a matter of what this person is trying to express. And I find it, I mean, disturbing as a speechwriter but even more disturbing just as an American.

GROSS: Let me reintroduce you here. If you're just joining us, my guest is David Litt. And he wrote speeches for President Obama from 2011 to 2016. He was a senior presidential speechwriter by the time he left. He's written a new memoir called "Thanks, Obama." And he is now the head writer and producer for Funny Or Die in Washington, D.C. So we'll be back after we take a short break. This is FRESH AIR.

(SOUNDBITE OF FLORATONE'S "FRONTIERS")

GROSS: This is FRESH AIR. And if you're just joining us, my guest is David Litt. He wrote speeches for President Obama from 2011 to 2016. He's written a memoir about that called "Thanks, Obama." And he's now the head writer and producer in Washington, D.C., for Funny Or Die.

So let's talk about getting vetted for this job.

(LAUGHTER)

GROSS: What kinds of questions were you...

LITT: Let's talk about it.

GROSS: Yeah, what kind of questions were you asked that you weren't sure how to answer, such as (laughter) when was the last time you smoked marijuana? Or how much have you smoked? I forget which it was.

LITT: Yeah, it was how much you've smoked. So you fill out this form. I filled out this form called the SF-86. And the SF-86 is this giant pile of papers. It's more than 100 pages long. And you fill out everything you've ever done in your life - so every address you've ever lived at. I filled out every job I had ever held for - no matter for how long.

And the part of the questionnaire that really scared young people, especially young Democrats in Washington when I got my White House job, was the part about drugs because they say, list every instance of illegal substances you have ever used.

GROSS: (Laughter).

LITT: And there was this question of, OK, well, I'm going to do what the form says. But I also want to make sure that I still get this job. What are the rules? What are the unwritten rules about this? Because it used to be that if you had ever smoked marijuana, you were automatically disqualified from a job like the one that I held. And over time, that clearly was no longer going to work, and the government relaxed its rules a little bit. But they didn't exactly explain how they were relaxing these rules. So the rumor mill kind of churned about what would get you disqualified from a job and what you could comfortably say.

So I was a little bit lucky. I - my pot-smoking career had ended in college because I briefly thought I might want to join the CIA. And I never got back into smoking marijuana. But it was still a question of, do you want to list everything? And what I remember was - so I went through, and I did some math. And I listed 30 instances of marijuana use. I did it sort of as a - let's assume I inhaled this many times a week for this many years. We end up at 30.

And then I also did add one experience I had with hallucinogenic mushrooms. But I also - I felt like it was important to make clear kind of in parentheses, but I didn't enjoy it. I wanted to make sure that nobody in - nobody reading the form would wonder, am I, you know, going on some sort of trip while I'm at the White House.

But it is funny that the vetting process takes me back to this time when that was the sort of thing that could get you disqualified from a White House job. I talk about the more subjective side of vetting. And in the first draft of the book, which I wrote before President Trump won, I remember writing, if you tweeted about female anatomy or spun records under the stage name DJ White Power...

GROSS: (Laughter).

LITT: ...You probably wouldn't get a White House job. And then as I revised and the Trump administration was beginning, I realized I had to change all the tenses on that sentence because probably, DJ White Power does get a White House job today. It was a very strange thing to figure out.

GROSS: You've kidded that one of the reasons why you wanted to become a speechwriter for President Obama is because you wanted to be his best friend, which, of course, was not going to happen. But you decided to leave about a year before Obama's presidency ended because of burnout, which is a real common problem I think for anybody who's worked in the White House.

So I guess I have a double question here as, like, when did the burnout outweigh the privilege and the specialness of working in the White House? Like, what was the tipping point for you? And was it hard to leave knowing that, like, not only weren't you going to be the president's best friend, but you'd probably, like, never see him again? Or maybe you'd never see him again.

LITT: The moment I knew it was time to leave the White House was the day that the marriage equality decision came down from the Supreme Court. So gay marriage was suddenly legal in all 50 states. And our intern was celebrating, and I remember looking at her and saying, just so you know, it's not always like this. And I had that voice in my head say, uh-oh, it's time to get out of here. I realized I was in danger of losing some of that idealism and that drive that brought me to D.C. in the first place. And I didn't want to become the kind of person who assumed that I was indispensable to the president or that the country was going to fall apart without me. So it was sad.

It was bittersweet knowing I somehow was in a position where I got to regularly interact with the president of the United States, and that wasn't going to happen again. But it also seemed so surreal and so much luckier than I ever could've imagined that I got to do that at all that I didn't find myself saying, oh, I have to do this another two or three times. It was more - it was kind of - it was like winning the lottery. It was this moment of saying, I got unbelievably lucky, and I'm just going to enjoy that.

GROSS: Did you miss it when you left? And have you seen the president since? Have you seen Obama since?

LITT: So I missed - I do miss parts of working in the White House. There's things I don't miss - the feeling that if I don't do a good job on a given day, the only person I'm really letting down is myself. I'm not letting down America or the president - in even a small way, is liberating. And it feels much more relaxing in that way. I miss being part of something that's so big. And I miss helping people - not the president, but Americans. I miss helping highlight their stories and bring them to national attention. That was a special thing.

I did meet the president one time since I'd left. White House staffers got to take departure photos. So you bring your family into the Oval Office. I brought my parents. I brought Jacqui. The first thing President Obama did was he looked at my parents, and he said, all right, who does he get a sense of humor from? And the answer is neither of them. But both of my parents immediately were like, oh, yep, that was me. It was all me. And I have never seen them act like that around anybody. It was amazing to watch this.

And then he turned to me, and he said, so what are you working on now? And I said, well, I'm trying to write the first-ever self-deprecating White House memoir. And I remember he looked at me, and he did not miss a beat. He just said, hmm, that seems like a contradiction. And then that was our last interaction. So it was this special moment where you realize that the president of the United States knows who you are and even the littlest thing about you. And I don't really feel like I miss that as much as I just feel incredibly lucky that that got to be my life for a little while.

GROSS: Well, David Litt, thanks so much for talking with us.

LITT: Thank you. This was great.

GROSS: David Litt's new memoir about writing speeches for President Obama is called "Thanks, Obama." After we take a short break, Ken Tucker will review two new albums by the band Deer Tick. This is FRESH AIR.

(SOUNDBITE OF THE WESTERLIES' "HOME")

TERRY GROSS, HOST:

This is FRESH AIR. It's been three years since the last release from the Rhode Island band Deer Tick. The quartet is back with two new albums titled "Deer Tick, Vol. 1" and "Deer Tick, Vol. 2." The first is mostly quiet, the second, mostly loud. And rock critic Ken Tucker says both have songs well worth paying attention to.

(SOUNDBITE OF SONG, "JUMPSTARTING")

JOHN MCCAULEY: (Singing) Afraid to say that you need a jumpstarting - anything to get you off of that cross. If you feel like your friends are parting, I can be your rock.

KEN TUCKER, BYLINE: I care is the key phrase in the refrain John McCauley sings on that Deer Trick take song called "Jumpstarting." For a guy who spent a good part of his band's career doing his best to act like a party animal who doesn't care, we must take this as a step forward in emotional maturity. These two new Deer Tick albums may separate in terms of volume. The electric guitar from the song I just played is from "Vol. 2," the loud one. But they're united in certain themes. Take, for example, the more quiet "Vol. 1," where the song "Cocktail" elaborates on the caring side of McCauley.

(SOUNDBITE OF SONG, "COCKTAIL")

MCCAULEY: (Singing) I started missing the days where as soon as I'd wake, I'd make a cocktail. I'd spend the time that you took giving me dirty looks with my cocktail. And just like every love affair on the fogged tin my armor shows, on the bullet shot full of hope. And I get a little green. I could be dancing on one leg and enjoying the masquerade. Well, I'm not making any lemonade, but I got lemons if you need.

TUCKER: "Cocktail" is an engagingly ambivalent song about emotional sobriety, as John McCauley wonders whether being alert and present for his friends in trouble or in despair is worth experiencing their pain. It's a notion he picks up again in "Don't Hurt" as he hazards a guess as to who's going to help him when he's hurting.

(SOUNDBITE OF SONG, "DON'T HURT")

MCCAULEY: (Singing) I'm not sure if I'm entitled to anything I feel. The only friends that I can trust are my Ford's spinning wheels. One more curve, maybe it won't to find you in my way. Forget my face. I'm just a name, a smile by mistake. So I hurt in your long and quiet hours. If I bite, all my wounds are tasting sour.

TUCKER: With two albums of ten songs each, there's room for band members other than McCauley to offer some welcomed new ideas. Deer Tick began as a solo project from McCauley. But over the years, the three other members have demonstrated how essential they are. In 2011, drummer Dennis Ryan wrote and sang the prettiest song on the album "Divine Providence." Now on "Vol. 1," he's given us another high point, "Me And My Man" about the romance of male friendship and more.

(SOUNDBITE OF SONG, "ME AND MY MAN")

DENNIS RYAN: (Singing) Me and my man goes walking around the block. Me and my man ain't got time to stop and talk, got too many games to play. Oh, boy, my man looks after me. Me and my man, me and my main man, me and my man, me and my main man running fast - catch us if you can.

TUCKER: The largely acoustic "Vol. 1" has a number of lovely melodies. But overall, I'd have to give the edge to "Vol. 2" where Ryan's pounding drums and the band's thundering guitars and electric piano send the music hurdling along with an urgent intensity. On "It's A Whale," McCauley's echo-off-the-wall squawk reminds me of early-period Alice Cooper, as does the song's satiric lyric about rock star proclamations of martyrdom and living on borrowed time.

(SOUNDBITE OF SONG, "IT'S A WHALE")

MCCAULEY: (Singing) Heading nowhere with the last of my kind. I'm a martyr, and I live on borrowed time. And I'm fine. Hey.

TUCKER: Frontman John McCauley is no longer content to merely bellow and shred his vocal chords. He's hitting the notes. More significantly, Deer Tick has become a more cohesive band. If the motive behind putting out two albums with contrasting volumes was intended as a demonstration of ambition and range, well, mission accomplished.

GROSS: Ken Tucker is critic-at-large for Yahoo TV. He reviewed the new album "Deer Tick, Vol. 1" and "Deer, Tick Vol. 2." Tomorrow on FRESH AIR, Candice Millard will talk about her new book about the young Winston Churchill. I hope you'll join us.

(SOUNDBITE OF DEER TICK SONG, "TINY FORTUNES")

GROSS: Fresh Air's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our associate producer of digital media is Molly Seavy-Nesper. Therese Madden directed today's show. I'm Terry Gross.

(SOUNDBITE OF SONG, "TINY FORTUNES")

MCCAULEY: (Singing) Can you believe what he did to himself - spent tiny fortunes on powder and pills. And I know you wanted to have it some other way. Cut it out. Get the keys. Let me stay. Way up under this mountain of scum, we look up at the strangers above. And I know you wanted to have it some other way. Cut it out. Get the car. Let me stay. Well, I've been looking at the black top waiting for you. Well, you can't understand it. You can't handle that I was having a good time while you were having a hard time. But you were having a good time, too.

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