How do you write a joke for the president of the United States? How do you come up with something that will seem perfectly cutting but not too cruel, silly but not stupid? How do you not denigrate the highest office in the land with — sniff — comedy?

Those were all questions David Litt, a speechwriter for President Obama and one of the folks most instrumental to Obama’s comedy monologues at the White House Correspondents Dinner, had to face when he worked in the White House. And after he left, he wrote his memoir Thanks, Obama: My Hopey, Changey White House Years, a whole book about his time working for the president, complete with lots of advice on how to write jokes for the president.

Todd talks with Litt this week about the strengths and limitations of political comedy, the joke he wrote for Obama that he’s most proud of, and the similarities between working at the White House and his new gig at Funny or Die.