Where They Are Now

He tried for the CIA. Comedy was more fun.

David Litt ’08 was the “token funny person” on Barack Obama’s speechwriting team.

Courtesy David Litt

Courtesy David Litt

Former Obama speech-writer David Litt ’08—shown here between Keegan-Michael Key and President Obama—became “the token funny person” on the White House speechwriting staff. View full image

David Litt ’08 is author of the New York Times bestselling memoir Thanks, Obama: My Hopey, Changey White House Years. A former editor-in-chief of the Yale Record, Litt wrote speeches for President Obama from 2011 to 2016; he was the lead writer for four White House Correspondents’ Dinner monologues. He is currently the head writer/producer at the DC office of the humor website Funny or Die.

Yale Alumni Magazine: Did you start out in comedy or politics?

David Litt: My junior year I interned at the Onion. My two jobs there were to catch typos and write jokes about the weather. By the end I was thinking maybe comedy is not something I want to go into.

Y: So instead . . . ?

L: I applied to join the CIA.

Y: Clearly the only other option.

L: Some recruiter came, and I sort of figured, “I directed my improv comedy group. I did a Light Fellowship to learn Chinese. I would probably not have been good at catching Bin Laden . . .”  But my interview was cut short when I admitted that I had smoked weed two months prior. That was the end of my CIA career.

Y: And yet you still ended up doing government work.

L: It was January 3, 2008. I was on a plane, watching TV, and I saw [candidate] Barack Obama speaking. It’s very rare that you can look back on a moment that changed your life—and most of those moments aren’t good ones. But by the time that plane landed, whatever Barack Obama was doing, I wanted to be a small part of it. I did a lot of volunteering on campus. I spoke about Obama incessantly. As you can tell, I haven’t stopped.

Y: A believer.

L: Two weeks after I graduated, I got in the car and drove to Ohio, where I worked as a field organizer. My job was to talk to Obama supporters and convince them to talk to their neighbors to convince them to volunteer. It was good training for speechwriting.

Y: Which you got into how?

L: I moved to DC and found an internship at West Wing Writers, which is run by former speechwriters for Bill Clinton [’73JD], and I ended up learning, without meaning to, an actual skill.

Y: And that skill got you hired by the White House.

L: I sort of carved out a niche of writing speeches that nobody wanted to write. But then our in-house funny person left, so kind of by default I became the token funny person.

Y: What was the funniest moment in the Oval Office?

L: We had a set of slides of the president with the first lady and her new hairstyle, and we were going to use them at the Correspondents’ Dinner. But then the day before the dinner I got a call from someone on the foreign policy side of our team who said, “Is the joke here that the president looks like Hitler?” And I don’t know exactly why this was, but for whatever reason, in that light, at that angle, even without the mustache, the resemblance was uncanny.

Y: To Hitler???

L: The next day, in our final meeting, the president said, “What happened to that third slide? I kind of liked that one.” And someone said, “We had to cut it.” And the president said, “Why?” And there was a very long silence, and then I heard myself say, “Um, Mr. President . . . I’m sorry but you looked like Hitler in it.” I had no idea how he was going to react.

Y: And that’s when you lost your job?

L: To his credit, he laughed harder than at anything else I ever saw him laugh at. He clutched his knees to his chest—he was knocking back into the couch.

Y: What happened to the photo?

L: It’s in the archives somewhere.

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