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The Schmooze

Inside The White House Correspondents’ Dinner With Obama’s Former Joke Writer

Barack Obama’s former speechwriter is opening up about what it was like writing jokes for the president — and his thoughts on Donald Trump skipping The White House Correspondents’ Dinner.

David Litt, who currently heads the comedy series “Funny or Die” told Vulture that he balanced his formal speechwriting duties with writing quips for the former president.

“There was one year where I was working on the Correspondents’ Dinner and simultaneously working on a speech about the Holocaust, so it was a very weird headspace to have to spend the morning on one and the afternoon on the other,” he said.

Preparation for the Correspondents’ Dinner was the equivalent of sitting in a television writers’ room, with speechwriters coming together with high-profile comedians, including Judd Apatow, to pitch jokes. Unlike writing individual speeches, this was not a one-person job.

“It would be very, very hard for one person to write the Correspondents’ Dinner on their own,” he said. “Jokes are just different than speeches in that way. Every line needs to be the best possible version of that line, and it’s all new, it’s all original.”

Litt added that Obama’s own personal gravitas helped lighten the writers’ loads.

“Part of what made writing jokes for the president a lot easier than writing jokes for a lot of other politicians is that he has that performer’s sense of self-awareness,” he said. “He could pull off a joke…because he knows, Okay, this is how I’m being perceived. That is not a requirement to be a senator or a president, but he happened to possess that.”

Once jokes has been narrowed down to a select few, they were brought to the president, who would then cut the ones he didn’t like, or try to shape the ones he thought needed work. Notes were never about making the quips tamer — if anything, it was the exact opposite.

“He would read something and say, ‘This is pretty good, but could we go a little edgier, a little sharper with it?’ ‘Sharper’ and ‘edgier’ were his two big notes, so you went back to your office feeling free to take an even bigger swing.”

And Obama’s favorite joke?

“The joke I wrote that he liked the most was from 2013, when he said, “You know, Republicans all agree they need to do a better job of reaching out to minorities. Call me self-centered, but I can think of one minority they should start with,” Litt recalled. “And I think he ad-libbed something like, “Think of me as a trial run.” It was fun when he would play off something like that.”

Litt went onto emphasize the importance of the Correspondents’ Dinner, and criticized Trump’s decision to skip out this year.

“Donald Trump is a bad person and that is reflected in his decision-making,” he said. “I don’t say that lightly. I don’t say that a lot of people are bad people. What I mean by that is, he does not understand the value of a free press. He doesn’t understand the value of being able to joke about yourself or admit that it’s a democracy.”

Thea Glassman is an Associate Editor at the Forward. Reach her at [email protected] or on Twitter at @theakglassman.

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