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What it’s like to write jokes for President Obama

Cody Keenan (then a White House speechwriter, now director of speechwriting) dresses up as a pirate for a 2009 White House Correspondents' Dinner gag.
Cody Keenan (then a White House speechwriter, now director of speechwriting) dresses up as a pirate for a 2009 White House Correspondents' Dinner gag.
Pete Souza/The White House

For President Obama's speechwriters, senior advisors, and other people who work in the West Wing, the White House Correspondents' Dinner is one of the toughest work weekends of the year. Writing for the WHCD means prepping the leader of the free world for the country's biggest stand-up act.

It’s not as if the president is only allowed to be funny once a year, of course. President Obama has slow jammed the news with Jimmy Fallon, practiced his cringe humor with Zach Galifianakis, and joked about his greying hair more times since taking office than all other presidents before him. (We’re still verifying that last number.) But the WHCD is different than Obama's other humorous public appearances.

Jeff Nussbaum, partner at the speechwriting firm West Wing Writers and a founder of The Humor Cabinet, says the secret to the WHCD’s popularity is that it’s the closest most of us will ever get to having a drink with the president. While appearances on late-night shows are staged policy pitches, and only the most elite Washingtonians will ever see invitations to the Gridiron Club or the Alfalfa Club, any American can watch the president bust some chops at the WHCD.

"Traditionally in Washington, the rooms in which Presidents told jokes were very exclusive and very private," Nussbaum said. "With the Correspondents' Dinner, you feel like when you’re in the room or, when you’re watching on TV, that you’re being let into what it feels like when people are breaking tension in the Oval Office or the Situation Room or the Roosevelt Room."

Why tell jokes?

Nussbaum, who has written for Al Gore, former Senate Majority Leader Tom Daschle, and Vice President Biden, explained that humor allows the president — or any political leader — to shed the weight of formality that comes with the office: "My unfunny philosophy on humor as a general matter is that it’s a means of characterizing yourself. A politician who is willing to tell a joke is someone people are willing to spend time with. Someone willing to tell a self-deprecating joke is someone who isn’t as pompous."

Jon Lovett, a former Obama speechwriter, shared the sentiment. "When there’s a great joke in a speech it can travel further, help more, than any litany of policies or great defense or argument. It cuts through that. It says, 'Look, we’re on the same page, we think this is crazy.' It says, 'Look, we understand this in the same way' — to the point we can laugh at it."

Lovett recalled that while writing the 2011 State of the Union, he had to fight to keep a decidedly tame joke about government bureaucracy in the speech. "It wasn’t the best joke in the world, but it wasn’t the worst either. When we were editing the speech, I remember one department thought we were mocking the other. It was that kind of fight, but we decided it was worth the risk. We said, ‘No, we’re just poking fun at government bureaucracy, and that’s the point of the section and the point of the whole speech.’ We fought to keep it in and the president delivered the line:"

Then there’s my favorite example. The Interior Department is in charge of salmon while they’re in freshwater, but the Commerce Department handles them when they’re in saltwater. I hear it gets even more complicated once they’re smoked.

The next day, NPR asked listeners to describe the speech in three words, then created a word cloud of their responses. "Salmon" dominated that graphic. Lovett is still pleased. "To those listeners, the State of the Union ended up being a speech about salmon with a few asides about jobs and the economy," he said. "It just demonstrates how much a joke can stick."

Presidents have been making jokes to that end for decades. Nussbaum pointed out that in President Kennedy’s 1962 "moonshot" speech at Rice University, one of the most famous lines is punctuated with a joke mocking the university’s football team:

But why, some say, the moon? Why choose this as our goal? And they may well ask why climb the highest mountain? Why, 35 years ago, fly the Atlantic? Why does Rice play Texas?

We choose to go to the moon. We choose to go to the moon. We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard…"

(The University of Texas was undefeated and Rice was winless at that point in the year. The two teams went on to tie a month later.)

Humor also allows a politician to stick a dagger in opponents in a way that would be considered mean-spirited if not done with a smile, but there are limits. When humor is wielded as a weapon, especially by someone with as much clout as the president, it can be easy for a joke to go too far. Masking a jab with laughter is a delicate art — one that President Obama has had to learn the hard way.

During a 2008 primary debate, then-Sen. Hillary Clinton was asked if she was personable enough to beat then-Sen. Obama. Obama interjected, saying: "You’re likeable enough, Hillary." That one comment, presumably intended as a joke, earned the him more than a little blowback. More recently, at the 2013 Correspondents' Dinner, Obama said basically the same thing about Senate Minority Leader Mitch McConnell, but to much more amicable effect:

Of course, even after I've done all this, some folks still don’t think I spend enough time with Congress. "Why don’t you get a drink with Mitch McConnell?" they ask. Really? Why don’t you get a drink with Mitch McConnell?

There was certainly more context to why the jab at Clinton earned backlash and the joke at McConnell’s expense was effective. The Clinton comment came after Obama’s stunning victory in Iowa, and at a time when gender was a growing issue on the campaign trail. The comment was widely perceived as condescending and dismissive, and Clinton would go on to win the New Hampshire primary (and 12 percent more votes from women in that contest). But the fact that the McConnell remark was made at the WHCD, where people are more willing to roll with jokes, was no small factor.

A well-executed joke is also an effective way to sweep away ongoing controversy. Early in Obama’s presidency, the backup plane to Air Force One flew low over Manhattan one morning without any warning, so photographers could snap it flying by the Statue of Liberty. The flight terrified people throughout the city — which was all the more infuriating since the purpose was so seemingly trivial. But at the Correspondents' Dinner shortly thereafter, Obama addressed the incident head on. "Sasha and Malia aren't here tonight because they're grounded. You can't just take Air Force One on a joyride to Manhattan. I don’t care whose kids you are." With one joke, the issue was settled:

Who writes the jokes?

The president employs a staff of speechwriters and communications specialists year-round to help shape the comments he makes during nearly every public appearance. In a few high-stakes instances — namely the State of the Union and Inaugural addresses — outside writers will be consulted. The WHCD has risen to that level of importance.

In recent years the president’s team has started to look beyond their inner circle for good jokes, receiving input from comedians, friends, advisors, TV writers, and various media personalities. Increasingly, submissions are coming in unsolicited. Lovett, on the Obama team for three years, said: "It’s not so much about balancing inside the White House with outside voices as much as it is drawing on as many talented people as you can. Some administrations have handled it in different ways. Some relied entirely on outside help. We [the Obama White House] had a good mix of jokes coming from outside and in."

The crack team of humorists that come on board to write jokes are less often Bruno Gianelli-esque hired muscle and more frequently old friends of the in-house talent. Regardless of their origins, the job of the outsiders, as Nussbaum explains it, is to set the mood and put everything on the table in the name of laughs.

"When you come in, you’re explicitly asking for the dispensation to be the one who won’t get yelled at for crossing the line. Sometimes the only way to know where the line is of what a president will or won’t say is by seeing it in the rearview mirror. You want to be open to everything in the brainstorm: every topic, proper or improper."

But according to Lovett, Obama himself is often the one looking to get closer to the line. "It’s one of the reasons he succeeds at these dinners. He’s not afraid to push. But he knows there’s also another side. If you tell a clunker, there’s a way a bad joke is especially jarring. It says, 'I thought you’d find this funny, but you didn’t because I didn’t understand you in this moment.'"

And there’s the rub. The dinner may be the closest you get to having a drink out with the president. The tricky part for him and his writers is making the hang-out fun.

Mike Case is the product chief of staff for Vox Media. He knows a thing or two about White House wordsmithing from his two years as director of presidential writers for President Obama.