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Obama speechwriter David Litt on the jokes the president can and can’t tell

“The most important thing about the president telling any joke is it’s the president telling a joke. That’s where the comedy comes from.”

Barack Obama Addresses White House Correspondents Dinner
President Barack Obama appears at the 2015 White House Correspondents’ Dinner with Keegan-Michael Key in character as Obama’s anger translator “Luther,” a bit David Litt helped facilitate.
Olivier Douliery-Pool/Getty Images
Emily St. James was a senior correspondent for Vox, covering American identities. Before she joined Vox in 2014, she was the first TV editor of the A.V. Club.

How do you write a joke for the president of the United States? How do you come up with something that will seem perfectly cutting but not too cruel, silly but not stupid? How do you not denigrate the highest office in the land with — sniff — comedy?

Those were all questions David Litt, a speechwriter for President Obama and one of the folks most instrumental to Obama’s comedy monologues at the White House Correspondents’ Dinner, had to face when he worked in the White House.

And after he left, he wrote his memoir Thanks, Obama: My Hopey, Changey White House Years, a whole book about his time working for the president, complete with lots of advice on how to write jokes for the commander in chief.

Litt joined me for the most recent episode of my podcast, I Think You’re Interesting, and I wanted to ask him not just about his book but about the process of writing comedy for the most powerful person on earth. Is it possible to tell jokes that punch up — the comedy term for jokes that make fun of those more powerful than the comedian — when the person delivering the joke is the president? And what sorts of jokes can’t the president tell?

Litt’s responses to those questions, lightly edited for length and clarity, follow.

Todd VanDerWerff

The bulk of your book is about your time working in the Obama White House, but a lot of it is about writing comedy for the president, which seems like a really tricky needle to thread. Not even just Obama, but with any president, what’s a joke you can or can’t tell with someone that powerful?

David Litt

There’s two different questions there. One is, what can you not do because it’s inappropriate? The other is, what can you not do because it’s just not funny if a president does it? The most important thing about the president telling any joke is that it’s the president telling a joke. That’s where most of the comedy comes from. That means that the bar of what’s edgy, what’s out there, is a lot lower than it would be if I was writing jokes for a comedian.

2017 Moth Ball: A Moth Summer Night's Dream
David Litt.
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Different presidents have been approaching this in different ways. Ronald Reagan was very funny, but in the much more classic, like, “Let me tell you a story about a cow, a farmer, and a sheepdog,” kind of thing. And he told good jokes like that. With President Obama, it was definitely not those kind of story, setup, punchline jokes, but more like observation and then a punchline to it.

To try to answer your question a little more succinctly, I think that the No. 1 topic that we would not joke about was national security. That was important to us, because one of the things about writing jokes for a president is if you have the joke and it’s totally in good taste, but then a week later, something happens — there’s a tragedy, there’s a shooting, there’s a terrorist attack — the joke can become retroactively in bad taste. That was an important thing for us. We didn’t want anything to end up in a campaign ad, and we also didn’t want to do anything that was insensitive and diminished the office.

The other thing was it was important that the jokes were an extension of who President Obama was the rest of the time. An example is every year, I would get pitched jokes — and this was totally fine, because our goal was to get pitched everything — about Chris Christie where the butt of the joke was that he was a big guy. We just didn’t want to make jokes about someone’s physical appearance. We made fun of him for Bridgegate, for shutting down traffic and all of that, the scandal and the arrogance and all of those things. That was fair game.

But when President Obama made fun of Trump, which he did frequently, he didn’t make jokes about his hands or he didn’t say, like, “Oh, he’s orange.” This was stuff that was focused on who this person is politically and the choices they’ve made, rather than their physical appearance. That’s a reflection of who President Obama is.

Todd VanDerWerff

There’s this theory in comedy of punching up versus punching down — trying to make jokes about people who either are on sort of the same level as you or have more power than you. But the president, theoretically, has the most power of anyone in the world, unless you’re joking about God; that’s the only way to punch up. So how do you find ways to tell those jokes without coming off as mean?

David Litt

There were two approaches. One is, yes, the president is, by definition, rarely punching up, in terms of just who has more power. Who can order a drone strike on who? The president’s going to come out on top of that conversation most of the time.

I do think self-deprecating humor is a way to even out that a little bit. For example, usually in one of the president’s White House Correspondents’ Dinner monologues, the first couple of jokes and then throughout, we would sprinkle some jokes where he’s making fun of himself. We tried to make those as real as possible. They were legitimate jokes where he was taking himself down a peg, in part I think because he enjoyed that and saw the value of it, but more than that, or in addition to that, there was a sense that that gives you the license to then talk about people who really bug you a little bit.

I think what we would have said was we weren’t punching so much as truth-telling. That was the euphemism that we used, but there was some truth to it.

In politics, you so rarely get outside the back-and-forth, where you say something and then someone else says the opposite, and regardless of who’s right, it gets covered as a controversy or a debate rather than a statement. Jokes were a way around that.

For example, when President Obama was making fun of something Mitch McConnell did, or making fun of Ted Cruz for having a big ego, I don’t think that those were moments where he’s punching down. I wouldn’t say he’s punching up, exactly, but he’s kind of lifting the lid on something that everyone in Washington knows and thinks about, but we’re not allowed to say because of the conventions of DC — or at least pre-Trump conventions of DC.

For much more with David Litt, on the strengths and limitations of political comedy, the joke he wrote for Obama that he’s most proud of, and the similarities between working at the White House and his new gig at Funny or Die, listen to the full episode.

To hear more interviews with fascinating people from the world of arts and culture — from powerful showrunners to web series creators to documentary filmmakers — check out the I Think You’re Interesting archives.