44 seems to have gotten this one right.

During his five year stint as a speechwriter in Barack Obama’s White House, David Litt wrote his fair share of one-liners for the nation’s most powerful man. But one of his brainstorms never made its way out of the president’s mouth. “It went along the lines of ‘Washington just legalized marijuana and we’re about to see big changes,’” Litt tells Moneyish. “For instance, Sen. Rand Paul just delivered a 13-hour filibuster as to keeping Taco Bell open.”

Us too, Mr. President.

“I’ve always liked that joke, but I’m in the minority there,” says the 31-year-old, who’s now head writer and producer of comedy platform Funny or Die’s D.C. operations. “That’s the thing about being a speechwriter—the boss is always right.”

Educated at Yale, Litt didn’t really get the politics bug until then-candidate Obama upset Hillary Clinton at the Iowa Caucus in early 2008. Inspired, he went on to work as an unpaid volunteer and then paid coordinator in the Illinois Senator’s presidential campaign, before winding up unemployed when Obama won. After several smaller gigs in D.C., Litt ended up as a speechwriter to Obama confidante Valerie Jarrett—partly because he was the only candidate.

“I was really lucky to write for her because she knew the Obamas better than anyone…they were like family for her,” Litt says. “She was often talking about the president’s judgment and why he did what he did, and that gave me a little bit of insight I wouldn’t have gotten otherwise into his character and values.”

Litt’s time at 1600 Pennsylvania Avenue, where he eventually rose to a senior post, is told in “Thanks, Obama,” a memoir of self-deprecatory tales out today. “I don’t see myself as a foremost authority on politics or Obama’s legacy,” he says. “But I am the foremost authority on how it felt being me, a small part of a big movement.”

(HarperCollins)

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If Litt was late-ish to politics, he’s long wanted to be a funny guy. While speechwriters are rarely acknowledged for their work—with George W. Bush aide David Frum’s “Axis of Evil” and Ronald Reagan writer Peggy Noonan’s “slipped the surly bonds of Earth” being exceptions —he was publicly acknowledged as the engineer of Obama’s viral collaboration with Keegan-Michael Key (Luther, POTUS’ Angry Translator) at the 2015 White House Correspondent’s Association dinner. (Noonan is a longtime columnist at the Wall Street Journal, which like Moneyish, is published by Dow Jones.)

“As a freshman in high school, I decided to do standup at a show and it went OK, so I kept doing it,” he says. Being funny in government though is another challenge altogether. “When you write an applause line for a politician, the difference between an A+ or B+ is not that great,” Litt notes. “But for a joke, the difference is everything. People either laugh or they don’t.”

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There are also constraints on what kind of jokes the commander-in-chief can crack. “Obama was funny and always thinking about the best way to reach people, but he never jeopardized any of our goals,” says Litt, adding that the ex-president had two red lines on humor. He always avoided mentioning his two daughters and anything about national security. “You want to be edgy, but edgy for a president,” Litt says.

The scribe doesn’t hide that he’s a fiercely partisan liberal—he muses in his book at how cool it would be to be friends with Obama—though he also professes grudging admiration at Sarah Palin’s oratory, noting how her popularization of the terms “death panels” fueled the anti-Obamacare movement. Furthermore, he acknowledges Donald Trump’s skill at getting the country to focus on whatever he says. That said, he’s not a fan of the former “Apprentice” host.

“He was in an environment against a candidate who self-professed to not being a political performer like Obama,” Litt says. “Yet he lost the popular vote and had a lot of help.” That’s also why he doesn’t think he could ever be like Stephen Miller and crank out lines for the current inhabitant of his former workplace. “If in some freak situation I had that job, I think I would resign,” he says. “Speechwriters don’t have to agree with every single word that comes from a speaker’s mouth, but you have to believe the person ultimately represents values you share.”

Litt left the White House a year before Obama did, though he still works alongside at least one former administration colleague at Funny or Die. “The hardest thing [about working for Obama] was the sheer amount of pressure,” he says. “Even if you’re doing the most low-level job, you feel that the country’s fate is in your hands. You can’t do the job well unless you have that sense of responsibility.”

That said, there’s one major perk of his former job that he misses—riding on Air Force One. “It was always really cool,” he said. “Now I just ride in the middle seat.”