As a freshman at Yale, David Litt ’08 bought a pair of Hulk-patterned pajamas. A few years later, he found himself wearing those same pajamas on an Air Force One flight to Germany.

On Thursday, Litt, who has written a New York Times best-selling memoir and four White House Correspondents’ Association dinner speeches for former President Barack Obama, returned to campus to speak about his experiences.

Just three years out of college, Litt became a speechwriter for senior White House staff and then served as a senior presidential speechwriter to Obama from 2014 to 2016. But Litt said he got his start in creative writing in a class he took at Yale, professor Anne Fadiman’s writing seminar “Writing about Oneself.” On Thursday, Fadiman introduced her former student, pulling out a decade-old copy of his application to her class and reading out a humorous poem from it. Several members of Fadiman’s class were also present at the event, during which Litt read portions of his 2017 memoir and shared his experiences as “token funny person” at the White House.

“When you start a job like the one that I had, you imagine two things — first, being able to make history and … [second,] being the person who can tell the president a hard truth,” Litt said.

But Litt joked that he missed his chance to tell Obama that “hard truth” when the former president mispronounced his last name as “Lips.” Instead of correcting Obama, Litt said to himself, “Okay, I guess I’m ‘Lips’ now.”

Throughout his speech, Litt described how he vacillated between “overthinking,” feeling nervous and listening to “Lips,” his bolder alter-ego who “didn’t give a f—,” while on the job.

Eventually, though, Obama got his last name right and Litt became more sure-footed and confident of his abilities. It was around that time that Litt, in an effort to quickly change into business attire, was caught by White House staff with his Hulk-patterned pajamas around his ankles mid-flight on Air Force One. Now, Litt says, some who travel on the plane occasionally attempt to recreate the infamous moment.

After his talk, Litt took several questions from the audience, often peppering his responses with passages from his memoir.

“The first time I became determined to work for Obama in any capacity whatsoever was the first time I heard him speak, when he said, ‘You represent the most American of ideals: Faced with impossible odds, those who love this country can change it,’” Litt reminisced. “I still think that’s true. Changing the country — if you love it — doesn’t have to be a full-time job, but I think it does have to be everyone’s part-time job.”

Since 2016, Litt has been the head writer and producer for the Washington, D.C. office of the video comedy website, Funny or Die. In that capacity, Litt was involved in Funny or Die’s recent campaign to spur interest in the upcoming midterm elections.

In an interview with the News, Litt said he has returned to campus every few years since graduation and that it is “always fun” to be back. He added that coming back and reading as a guest in his favorite class is like accomplishing a bucket list item that he did not even know he had.

Litt also offered some advice to student writers at Yale.

“Read everything you can,” he said. “The best writers are always people who are just curious about everything. And treat writing like a job … not like you’re just hoping that lightning will strike.”

Litt added that the biggest lesson he learned from his time at the White House is that everyone is human, including those who become society’s heroes, and that everyone has an obligation to do their part.

Head of Branford College Enrique De La Cruz said he thought the talk was “absolutely fabulous,” “funny” and “insightful” and offered “wonderful” advice for young adults. He added that he was indebted to Litt for having come and particularly grateful to Fadiman, who he said was instrumental in making the event a reality.

Audience members interviewed by the News said they enjoyed the talk.

“I loved it; he’s really funny,” said Berenice Valencia Fernandez ’18, a visiting international student and a staff reporter for the News. “Everyone is really moved by Obama’s speeches, and getting an insight into how they are produced was really interesting.”

Fernandez added that she appreciated Litt’s ability to joke about himself.

The event was co-sponsored by the Poynter Fellowship in Journalism and the Traphagen Alumni Speaker Series of the Yale College Office of Student Affairs. The Poynter Fellowship in Journalism was established by Nelson Poynter GRD ’27 to honor and bring to campus those who have made important contributions to the media.

Saumya Malhotra |