It's so unfair that Barack Obama, this cool, charming guy, also has good comedic timing.
— Jon Lovett
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.
If there is one way that I would sum up what the 2016 election was on cable news, it was world-class journalists interviewing morons.
Because the speech is an argument, and a great speech makes an argument well, the act of making that argument is a really important part of how the policy process coalesces and solidifies both for the candidate and also the people serving that candidate.
When in doubt, mock the powerful, not the powerless.
Part of my job as a presidential speechwriter (along with great writers like Jon Favreau and David Axelrod) was finding that sliver where 'presidential' and 'actually funny' overlap.
A boring speech can be just a boring speech. But a speech with a joke that falls flat is awful. I hate it. That's why I think it's easier to hate a comedy. If a drama doesn't land, it's boring; if a joke doesn't land - you hate that.
We don't want people to be afraid of saying something interesting on the off chance it's taken the wrong way.
America needs a strong, rational, positive, practical conservative movement. It needs that bulwark against liberal delusion and hubris. It needs a voice that says we are imperfect, that life is complex, that government can create need even as it meets need, that you can't fix everything, and freedom is worth some danger and sorrow.
I worked on one speech about the financial system that caused the Dow to drop, like, 200 points.
Life tests our willingness, in ways large and small, to tell the truth.
I am a deeply awkward person; I am not cool.
The conversation on Twitter and the way people are in the world are very different.
Republicans paint everything that Democrats have been for as socialism, too far to the left, as extreme, and it didn't matter how moderated it was; it didn't matter that Obamacare started out as a compromise. You might as well say what you're actually for and show what you really are.
Regardless of how lyrical or rhetorically gifted they are in conveying big ideas, any candidate can do a good job of giving a speech if the goal of a speech is more than just delivering it well but achieving some end, whether it's convincing people of some issue or persuading them about you as a person.
Humor connects us, especially in politics. It's a way of surprising one another with shared context and experience.
Kellyanne Conway is one of the most dishonest humans ever to grace the office she holds.
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.
We are drowning in information.
One of the hardest lessons of childhood is reckoning with the instability of the world.
I'll always cringe remembering those little embarrassing moments when I said something dumb on a conference call, when my inexperience poked through, when I should have been more solicitous of the judgment of those around me. They're a reminder that it's not mutually exclusive to be confident and humble, to be skeptical and eager to learn.
Washington is filled with people making other people's arguments for money.
Trump is a raptor testing the fences, and he found weaknesses to escape and try things that would work, every single day.
I had a really fun career in TV right after I left politics.
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.
A great speech can make you remember something about what you believe, about who you are, about who you want to be. It's rare when that kind of thing happens. But it is important, and it is real.
Everybody hates Congress; even Congress hates Congress.
When a joke works, it works. It can make a point in a really simple way; it can be a great little sound bite to put on television or share on social media. Humor has this incredible power in how we communicate about politics now, in part because there's something natural in the way it's communicated.
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.
The Internet didn't cause Donald Trump, and it certainly can't solve Donald Trump.
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.
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?
