What it's like to write jokes for President Obama

US President Barack Obama delivers the commencement address to the 2016 graduating class of Howard University on May 7, 2016.
US President Barack Obama delivers the commencement address to the 2016 graduating class of Howard University on May 7, 2016. PHOTO: REUTERS

US President Barack Obama and his anger translator were having issues.

The motorcade was scheduled to leave for last year's White House Correspondents' Association dinner in less than 20 minutes. We had one chance to rehearse the President's closing sketch with the translator, "Luther", who was played by the comedian Keegan-Michael Key.

Mr Obama had no problem delivering his lines or pretending to go unhinged when talking about climate change deniers. "I do actually get mad sometimes, you know," he said.

The problem was Luther. Each time Key, as the anger translator, began a new manic tirade, the President burst out laughing. Already dressed in his tuxedo for the evening, he glanced towards us, his staff, huddled in a corner of the room.

"I've got to hold it together," Mr Obama said. He said it again backstage a few hours later, this time using a comedy term for laughing in the middle of a scene. "I have to make sure I don't break."

He pulled it off. Like other leaders before him, Mr Obama has gamely played his part in the annual correspondents' dinner - the last one on April 30, his eighth, featured the comedian Larry Wilmore - and the large number of toasts, monologues and other comedic obligations that come with the world's most powerful gig.

Part of what makes any presidential joke funny is the fact that the President is telling a joke. But this President has a talent for comedy - an impressive sense of timing and audience. His administration combined that talent with an understanding of a changing media landscape and the emergence of viral videos. Jokes became a real tool to move his agenda forward.

When I began working for the White House in 2011, the most effective way to draw attention to even the most obscure policy issue was generally either an interview or a speech. There was no @POTUS Twitter account, no Facebook Live, no Snapchat. There was also no real evidence that, outside of the traditional Washington joke dinners, being funny could help a policy be taken seriously.

A turning point came after the somewhat-rocky autumn of 2013. That was when, as the President later described it in his 2014 correspondents' dinner speech: "We rolled out HealthCare.gov. That could have gone better." By March 2014, the healthcare exchanges were finally working, but most young people didn't seem to know that. Not enough of them were signing up. One solution, at least in part, was for Mr Obama to plug the site on the comedian Zach Galifianakis's online talk show, Between Two Ferns. The Commander-in-Chief sat between two ferns and listened as the comedian asked him, "What's it like to be the last black President?" before they got around to talking healthcare.

The day the "Ferns" video appeared online it was viewed by 11 million people, and traffic to HealthCare.gov spiked 40 per cent. Of course, that video isn't the only reason the administration can now report that 20 million people are enrolled in insurance through the Affordable Care Act. But it certainly helped get the word out.

Since then, the President has appeared on Marc Maron's podcast, guest-hosted a segment on The Colbert Report and driven across the South Lawn of the White House with Jerry Seinfeld in a '63 Corvette.

Of course, his most frequent target has been himself. He's made fun of everything from his hair going grey to his approval ratings going down. (This year they're going up, presenting an added challenge for the writers.) He's told jokes that set the tone for the year ahead. (2015: "My advisers asked me, 'Mr President, do you have a bucket list?' And I said, 'Well, I have something that rhymes with bucket list'.")

On occasions, he's used his comedic sensibility to tell some inconvenient political truths. (2013: Republicans agree that "they need to do a better job reaching out to minorities. And look, call me self-centred, but I can think of one minority they could start with".)

There are some topics no president, even a genuinely funny one, can joke about. National security is off limits. So are all but the gentlest mentions of the first family. Then there was the meeting in 2013 when, sitting on the surprisingly comfortable brown couches in the Oval Office, Mr Obama's speechwriters suggested he talk about Republican senators in the style of Alicia Silverstone's character from Clueless. Something like: "So then Mitch was talking with John who was talking with Lindsey who said that Rand and Ted were, like, talking?"

"This might be funny… if a professional comedian did it," the President said. We moved on.

Another joke he rejected involved the District of Columbia decriminalising marijuana, a Rand Paul filibuster and a congressional debate on "whether or not the Taco Bell is still open". He let us pitch him on it, but in the end it proved too clunky and complicated.

On April 30, the President delivered his final correspondents' dinner monologue. For weeks before that, writers in and outside the White House submitted hundreds of jokes, and only a handful of my former colleagues knew which 35 or 40 would make the final cut. A safe bet was that at least a few of the President's one-liners would look back on the last eight years. There was plenty of material to work with - an economic recovery, Obamacare, rescuing the auto industry. It seemed unlikely that "starring in viral videos" would be high on the legacy list.

But I do think that presidential comedy has played a role in this chapter in American history. The bully pulpit has splintered. It's become harder than ever to get people's attention. And the White House has recognised what class clowns have known all along: Being funny helps.


•The writer, a former White House speechwriter, is the head writer and producer for Funny Or Die DC. He is at work on a book about life as a 20-something in the White House.

A version of this article appeared in the print edition of The Sunday Times on May 08, 2016, with the headline 'What it's like to write jokes for President Obama'. Print Edition | Subscribe