Obama’s Funniest Speechwriter Explains How Trump ‘Gives Wedgies’ Instead of Telling Jokes

The Roastmaster General going for yuks at a MAGA rally.

The Roastmaster General going for yuks at a MAGA rally. Photo by Sean Rayford/Getty Images

When Lesley Stahl confronted President Trump on Sunday about mocking Christine Blasey Ford at a recent campaign rally, the exchange was yet another reminder of what passes for normal in the White House these days, where standard conventions of presidential behavior have been cast aside, even when it comes to humor.

“Why did you have to make fun of her?” asked Stahl. “Thousands of people were laughing at her.”

“You know what? I’m not gonna get into it because we won. It doesn’t matter. We won,” replied Trump. 

Subscribe to Observer’s Politics Newsletter

Throughout his presidency, Trump has displayed a comedic sensibility never before seen in the Oval Office. It’s a style he deploys both privately and publicly, according to Bob Woodward’s book, Fear, in which the president is said to call his own Attorney General a “dumb Southerner” and “mentally retarded” behind closed doors. Funny stuff.

Over the past few weeks, the Insult-Comic-in-Chief has appeared particularly loose, letting fly with his routine, without apology, to rile up the base. Two days after ridiculing Blasey Ford to huge laughs in Mississippi, Trump was at it again in Minnesota, directing zingers at former Senator Al Franken.

“Boy, did he fold up like a wet rag,” quipped Trump to an auditorium full of chuckling MAGAs. “He was gone so fast. It was like, ‘Oh, he did something, Oh, I resign. I quit.’”

The president might elicit easy group-cackles from his base, but from a comedic standpoint, the man can’t read a room. Outside the rally circuit, lines intended to be serious sometimes get the biggest laughs, as they did during his speech at the UN General Assembly, when world leaders erupted after Trump boasted that no “administration in the history of this country has done more in two years.”

“They weren’t laughing at me, they were laughing with me,” insisted Trump, like a delusional open-mic standup.

The stark contrast in comedic styles between Trump and past presidents came into focus last month when an exasperated President Obama took a rare swipe at him during a speech in Illinois. “How hard can that be, saying that Nazis are bad?,” asked Obama. To which a smirking Trump fired back, in a roast-worthy appraisal of Obama’s speech, “I fell asleep. I found he’s very good, very good for sleeping.”   

To former speechwriter David Litt, who was Obama’s lead joke writer on four White House Correspondents’ dinners, the clash was emblematic of the pair’s dramatically different approaches to presidential jest.

“Obama’s line got a laugh, but his point was serious—and not really about Trump,” Litt explained to Observer. “If politicians can’t immediately reject someone who can’t immediately reject Nazis, they shouldn’t hold office. But I’m not surprised President Trump took this personally. He takes everything personally, and his rebuttal—’I was supposed to be leading the country but instead I was watching TV at noon on a Friday’—was kind of a self-own.”  

As the head writer and producer for Funny or Die’s Washington D.C. office and the author of Thanks, Obama: My Hopey, Changey White House Years, Litt knows his way around a presidential joke. We asked him for some inside analysis on the new style of political comedy that’s taken over the White House.

Politics aside, what’s your take on President Trump’s particular brand of humor?
What’s interesting is that President Trump has a sense of humor. I think it’s a very classic bully’s sense of humor, like the kid giving another kid a wedgie on the playground. It might be amusing and entertaining to onlookers, but it’s not necessarily a well-crafted joke. And it’s using humor as a way of asserting status. So humor becomes this tool to remind people that you’re the dominant one in the room.

For example, he retweeted that video someone mashed up of Trump hitting a golf ball, and the golf ball hits Hillary Clinton in the back, and she falls down. That’s reflecting a sense of humor, but it’s a departure from past presidents where the idea of humor was to show how open and warm you are, as opposed to how dominant you are.

Do you think, as others have suggested, that the humor reflects the man in this case?
I wouldn’t overdo it—a person’s sense of humor isn’t entirely a window into their soul—but it does give you a peek. And the flip side is also true. President Obama when he told jokes was very confident, a little cerebral, and sort of self-effacing; but you never got the sense that he forgot who the president was. And I think that also reflected who he was as a person.

I think the fact that Trump doesn’t laugh matters. I think it’s a very strange thing. And I don’t know 100% what it means. Like if you went to a doctor and the doctor never laughed, or really smiled, you would feel uncomfortable around that doctor. The fact that we have a president who doesn’t laugh is not a good thing. I can’t tell you the contours of its badness, but I can promise you that it’s not good. And it’s very notable. I think his sense of humor is very much about “Who can I publicly disrespect and get away with it?” It’s joyful for him in a weird way, and I think that’s what people are responding to with their laughter. I wouldn’t call them jokes, it’s a different type of humor based on the idea that we’re supposed to treat these people with some basic decency—and I’m flaunting the fact that I’m breaking that rule.

The other thing I’d say about Trump as a joke teller is that it’s very notable that he hasn’t gone to the White House Correspondents’ Dinners. Because that audience—D.C. and New York journalists, Washington VIPS, Hollywood celebrities—that’s the group Donald Trump has spent his entire life hoping to impress. And I think there’s a weird irony to the fact that he became president in large part because it might finally make him part of elite society. He seems to have realized since then that he’s just not capable of winning over the people he’s spent his whole life caring about more than anyone else. 

So has Trump ever made you laugh?
Trump’s told plenty of jokes where I thought, Oh, that’s cute. The one that he’s told that I thought was legitimately very funny, although it was at his wife’s expense, was: “You want to know how unfairly I get treated in the media? Michelle Obama goes to the Democratic Convention, she gives this great speech. My wife gives the exact same speech and everyone hates her.” It was almost a self-deprecating joke, but it was actually deprecating his spouse. I don’t know if President Obama would have said it. I have a strong suspicion he wouldn’t have.  But I did think purely from a joke-writing standpoint that it was really funny. It was at the Al Smith Dinner, and within two seconds you had a joke that was like, “Hillary hates Catholics”—and I think that was the punchline of the joke. And he got booed. I think something happened where he kind of thought he was reading the room—and it turned out he wasn’t able to.

Do you think Trump has joke writers, or is he mostly ad-libbing?
Does it look written down to you? I don’t think so!  The Al Smith Dinner was very interesting, because on the first page, there were five or six jokes that clearly someone had written; one or two that were actually quite good—and then it totally went off the rails. And you got the sense that he was kind of ad-libbing or thinking: “I can do the punchline better,” and was wrong.

Look at his rallies, he gets laughs from the audience, I don’t think anyone is writing those jokes. Then again, the laugh tends to be about punishing enemies rather than about making friends, if that makes sense. Some people say, isn’t that insult comedy?  But not really when you’re a politician—it’s just kind of being a dick. You can be funny and still be a dick. The way to think about it is whether it’s bullying or not. With a joke, you’re able to be cruel to someone and get away with it. And I think that’s what makes that kind of joke funny.  

This happens sometimes among liberals now, where you can say “Donald Trump sucks,” and then people will laugh. But they’re not really laughing because of the beautiful construction of the joke; it’s kind of an agreement. A friend of mine who writes for SNL calls it “clapter.” And as a comedy writer she says she’s always trying to avoid that as much as possible; just saying something broadly popular where people aren’t really laughing.

Were there hoops a joke had to jump through with Obama before it got the green light?
I would draw the distinction between comedy events and regular speeches. In a typical speech, the joke would be just part of the speech. The president would read it when he read the rest of the speech. Obviously, if someone thought it was inappropriate they would say so, and we’d talk it out and decide whether to keep it in. And ultimately it would be up to POTUS to make that call.

For joke speeches, the biggest thing was that we would get pitched. When I was running the joke writing process, I would read maybe 600 jokes for every Correspondents’ Dinner monologue. And because I was writing regular speeches most of the time, you have a general sense of “Here’s what’s crossing a line,” in a bad way, and “Here’s what’s pushing the envelope,” in a good way. With some stuff you say, “You know what? This is just not going to happen,” because it doesn’t feel right for the president, in the same way that saying a serious line would not feel right. But I certainly never set any rules saying, “Here are the dos and don’ts for pitching jokes.”

How does Obama’s joke-telling style fundamentally differ from Trump’s?
We would never do a joke where the point was something sensitive about someone’s physical appearance. For example, every year a couple of jokes were pitched where the punchline was “Chris Christie is a large person.”

We might use a joke about Bridgegate—or something that we felt was actually a choice that he had made—but just making a joke where its like, “Hey, he’s overweight” seems disrespectful. And kind of cruel; there’s not really a reason, it’s just mean. And things that are sexist, things that are racist—obviously that’s never going to fly.

And the other thing, joking wise, anything about national security we wouldn’t joke about, even if it seemed okay at the moment. If events could make it look tasteless in retrospect, that was something we’d be careful about. For example, a pretty well-constructed joke Trump told at the Gridiron last year was: “I’m pretty open to talking to Kim Jong Un. For those who question the wisdom of dealing with an unhinged madman, I’d say that’s his problem.”

I didn’t find it funny because I found it a little too true. But that’s a well-constructed joke. We would never have said something like that, because what if you had a nuclear standoff? Suddenly, the fact that the president was joking about that means something very different, as it did on the night of the joke.

Trump’s handlers have often had to clarify to the media that he was joking about something, like when he accused the democrats of treason or encouraged police to act with increased violence. Kellyanne Conway complained that Washington is completely humorless and can’t take a joke. Is that your experience?
There was never a time when Barack Obama said something and we said, “Oh, actually he was joking.”  Do you know Mike Birbiglia, the comedian? In his special, Thank God For Jokes, he talks about how people will say something disgusting and then say “I was just joking,” as if that makes it better. If you have to say “I’m just joking” then it’s not a joke.

I don’t take that sort of defense very seriously. These are moments when it’s not apparent to anybody, including the presidential staff, that this was a joke—before there’s a controversy. What they’re really saying is, “You should be selective in which statements you take from the president seriously. And you should let us make those decisions well after the fact, not like 15 minutes but days after the fact, of what you should take seriously and what you should not.”

Which would be very convenient but that’s not how the world works. Not just politically, but other countries have to make decisions based on what the president says. Businesses make decisions based on what the president says. And citizens base whether their rights are in jeopardy based on what the president says.

It feels like Trump could defuse a lot of situations by being more self-deprecating. But is that even in his arsenal?
I think with Trump, when you peel it all back what you see is a lot of fear. This idea that if I were to say something that diminishes myself, even as a joke, people would realize it’s true. Where a Bill Clinton or an Obama or a Reagan took the opposite view that basically said: “Yeah, of course I can make fun of myself,” because that is a demonstration of strength and confidence.

In a very strange way we’ve never had a president so obsessed with looking tough. And we’ve never had a president so politically and also internally weak. And I think that’s reflected in the jokes. Or lack thereof.

I think what’s interesting is that he has been willing to be self-deprecating on a few things. Oddly his hair was one he has always been willing to talk about—I don’t know why, particularly—but you saw that on Jimmy Fallon too. He was fine about being teased about having not quite human hair. But you get a sense of what’s vulnerable and what’s really not—like you couldn’t joke about his money.

So how important is it for a president to be funny?
I don’t think it’s essential; I just think it’s useful. Being funny is useful in the same way that being charismatic is useful. We’ve had presidents who weren’t good speakers and we have had presidents who weren’t really good at schmoozing, and we’ve had presidents who weren’t that funny, but if you’re good at those things, it’s better than being bad at them.

Obama’s Funniest Speechwriter Explains How Trump ‘Gives Wedgies’ Instead of Telling Jokes