Punchlines and Politics: David Litt at Yale

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“I kind of fell ass-backward into speech writing,” David Litt ( BR ’08) told the crowd. 

What a thing for Barack Obama’s former speechwriter to say. In his rumpled, white shirt and with matter-of-factly clasped hands, Litt was exactly what you’d imagine a former White House denizen to be, with a quick sense of humor (he was also Obama’s joke-writer) to boot. Accustomed, maybe, to running on an accelerated national clock, Litt seemed to move in double time: each gesture swift, precise, and contained, as if he sat before us in a sped-up video. He was very much real, though, and LC 317 was packed with people who had come to see him. I was lucky to have nabbed a seat; the audience lined the windowsills, walls, and floor. 

Litt, former editor-in-chief of The Yale Record and former head of campus comedy group The Exit Players, served as a White House speechwriter from 2011 to 2016. His circuitous path to that position included an internship for The Onion and an (unsuccessful) application to the CIA, which seemed to suggest that government work was not in his future. Not so. Litt can pinpoint the day and moment that changed his life: January 3, 2008, mid-flight on an airplane, back in the days when watching TV midair was “a big deal.” Litt was watching CNN, and there was Obama at the podium, looking at America through the camera and telling everyone—telling Litt—how “in the face of impossible odds, people who love this country can change it.” By touchdown, Litt was convinced. He started volunteering on campus, worked as a field organizer for Obama in Ohio, and eventually began writing speeches. He has not looked back since. 

Having spent much of his career in speechwriting, Litt is highly attuned to his audience’s interests. Before we began, he invited us to share any questions or topics we’d like him to address so he could return to them throughout the event. In addition to these suggestions, he responded to pre-submitted questions read by David Acquaah-Mensah (BR ’25) of the Yale College Democrats, followed by more live questions from the crowd. (The event was jointly hosted by the Yale Dems and The Yale Record.) In a lively mix of jokes, anecdotes, and reflections, Litt spoke about his path from Yale to the White House, working with Obama, the art of jokewriting and speechwriting, his current projects, and more.

Some of Litt’s stories could have been lifted straight from the stirring plotlines of The West Wing. Asked to speak about his first formative experiences in politics, Litt described being a first-time field organizer in Ohio—stressed, nauseous, and responsible for overseeing an entire county (you know it wasn’t important because he was in charge of it, he joked). One day, a canvasser was taking calls while pacing around the office, which set him on edge—there were systems in place, protocols to follow, and desks for calls to be taken at—so he asked the caller to stay seated. “I can’t,” she said. She had three herniated discs, which made sitting excruciating. Taken aback by this news, Litt told the caller she could stay home rather than canvas through the pain. “No, I can’t,” she said again, because she was without health insurance to take care of those discs. She was there to get it. 

When asked what he had learned as a White House speechwriter, Litt responded that he doesn’t necessarily believe that he left the job as a better writer. Rather, he said, he became more sensitive to certain aspects of writing, like the many ways that language can be interpreted. Being a speechwriter in politics is especially challenging, Litt explained, because every line has the potential to be taken out of context  weeks or months later. 

Litt first learned this lesson after writing a joke responding to Obama’s birth certificate controversy: “You may think Tim Pawlenty’s all-American, but have you heard his full name? That’s right: Tim ‘bin Laden’ Pawlenty.” When the final speech draft was returned to him, someone had changed the line: “bin Laden” was now “Hosni,” in reference to a former president of Egypt. Litt was livid. The joke was all wrong. No one knew Hosni Mubarak. The hard syllables of “bin Laden,” which had added to its original humor, were no longer. Litt came close to taking a stand—of all the hills to die on, this was almost his—but ultimately refrained. At the White House Correspondents Dinner, the rewritten joke flopped. No one laughed. Litt’s vindication was short-lived, though. The next day, he received an email announcing Osama bin Laden’s death. The incident was his first glimpse into the tricky, delicate dance that political speechwriters must master in unpredictable circumstances. 

Litt was only 24 when he entered the White House. When asked about imposter syndrome, he described how strange it was to be so young in that position, feeling every day that they’d chosen the wrong guy. At that point, he said, it’s just about doing the work as well as you can. Someone once gave him the advice that imposter syndrome happens to everyone; he might as well be the one on the job. 

He was good at it, too. Joke writing, as he explained it, is a technical art: a form that pays attention to syllables and rhythms, timing and nuance, in a way that reminded me of poetry. It’s also a high-stakes game. As Litt pointed out, a failed applause line can go unnoticed (no one would know they were supposed to clap there!), but a poorly-landed joke sticks out like a sore thumb (cue the, as he put it, “sad trombone sound.”). Litt also noted the interesting way in which jokes can tell us about the people behind them.What politicians will joke about tells you what they’re confident in, he said. Take polling numbers. If they’re truly terrible, they’re not joke material. If they’re only somewhat terrible, that’s fair game. 

Not every speech is the place for joking, Litt emphasized, but jokes can be key for opening certain doors. Humor, after all, is human at a level that runs deeper than politics and policies. When writing speeches for new audiences, Obama’s writers turned to humor to establish common ground. Sports are a similar tool. Say Obama was giving a speech in a new city. If the Chicago Bulls had played the local team recently, Obama had his opening: “Too bad about those Bulls…” “Those Bulls, didn’t they play great?” No matter which team the audience had rooted for, Litt explained, they could all say in response, “Ah, those Bulls!”And the door was open.

Riveted as we were by stories of Litt’s career, all Yalies in attendance were especially keen to hear how he was impacted by his experiences on campus. Comedy, a skill Litt honed at Yale with The Record and The Exit Players, was definitely helpful. Of course, joke writing became important to his career. Improv with The Exit Players also helped Litt learn to think on his feet and enter an audience’s point of view, skills that proved useful to him in his early days of campaigning and writing for national and international listeners. Classes he took at Yale—he gave a shout out to Writing About Oneself, taught by Professor Anne Fadiman—also prepared him for the writing he would come to do. Then again, writing for another person’s voice is very different from writing for yourself. For those who are interested in learning speechwriting, Litt recommends West Wing Writers, which he credits with teaching him the craft.Litt has since transitioned from speechwriting to book-writing. In 2017, he published the memoir Thanks, Obama: My Hopey, Changey White House Years, followed by Democracy in One Book Or Less: How It Works, Why It Doesn’t, and Why Fixing It Is Easier Than You Think in 2020. Litt is now working on his third book, a comic memoir, which is set to release in 2025.

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