Whenever you're talking about using humor in politics or in a policy speech or in a serious moment, you're talking about using it as a tool to engage people. That's why putting a joke in a political speech is a luxury, and it is always a risk.
The great thing about writing jokes for President Obama is that he is not afraid to tell jokes that are actually funny - and not just funny for a politician.
There are a lot of heartbroken, anxious people that thought better of their country. We're heartbroken by how far Trump has gotten to the most powerful position in the world.
I'm not insulting Trump supporters; I'm calling the people that CNN puts on television terrible representatives of the views of conservatives.
It's a reasonable thing to tell somebody, 'I've watched 70 hours of 'Game of Thrones.'' That's a totally normal, boring thing to say about yourself. But if you were like, 'I just spent 100 hours playing 'Skyrim,'' people think you're a weirdo.
So often on CNN, there's a world-class journalist interviewing campaign rejects and ideologues and silly, craven people who do not care about informing people, that aren't there to help people understand what's going on in the news.
The First Amendment's protections have always put a great deal of responsibility in our hands: not only to respect the power of our own speech, but also to respect that same power in the hands of people we despise.
Sometimes you're going to be inexperienced, naive, untested, and totally right. And then, in those moments, you have to make a choice: is this a time to speak up, or hang back?
They're the last human beings susceptible to human shame. Politicians are the only people left for whom, occasionally, shame hurts them. Everyone else, we've sort of done away with it as a concept, and we're hurtling through space like animals, basically.
It was awesome how supportive the White House was. It meant a lot to me that when I left, the people that I worked with - Jon Favreau and David Axelrod and others - really understood that this was something that I felt I held had to do.
When I was a kid, all I knew about Michael Jackson was that he was crazy. He had a monkey named Bubbles and some kind of oxygen chamber, and he used to be black, but he made himself white, and he was nuts. That was Michael Jackson in full. Wacko Jacko.
There is that definition of leadership that says, 'Leadership is convincing people to do things that they otherwise wouldn't have done because you've made them believe it's the right thing to do.' And a great speech can do that.
I worked on one speech about the financial system that caused the Dow to drop, like, 200 points.
One of the hardest lessons of childhood is reckoning with the instability of the world.