Making time to prepare to host the White House Correspondents’ Dinner has not been easy. Presently I’m flying back to New York, where I live, on a red-eye after a show in Las Vegas. My wife and five kids, all under the age of ten, are at home waiting for me. On average, I have one media appearance every day and a half between now and then. I’m not asking you to cry for me. All of this momentum and publicity is terrific. And my preparation for the big night on April 25 is always simmering below the surface. It feels as if reading minds for the last 30 years has been training for this moment.
My goal is to have Donald Trump take part – and to save the best for last. If I could read only one mind in this world, it would be that of the most powerful person in the world. No one has ever really managed to predict what the President will say or do or think next. Maybe I will finally get a chance to unlock that puzzle. Trump is a figure unlike any other, and also in some ways the hardest to read. I think that’s by design. He has such an authenticity. You know that there is no way he would be in on what I’m doing. Everyone knows there is no motivating factor or anything I could do to make him pretend or act or do anything but be who he truly is. When I guessed Joe Rogan’s PIN on his podcast, you could see on his face a little bit of anger and discomfort and that feeling of, “Holy crap, how did he do that?” If I can do the same with Trump, it will be an exponential jump because he would never fake a reaction. And if his reaction is huge, it’s going to be the cherry on the ice cream sundae.
My planning is very psychologically nuanced and layered. I’m trying to prepare for every potential eventuality I can think of, while still getting the same great result. And I have a really clear vision for the stories that will be written the next morning: what happens in that room could go viral. My job is to deliver, very succinctly, the headline and the clip that everyone wants to click on – the news that will get sent around the world. (And will hopefully also be a real inflection point in my career, too.)
I also want to make sure that the 2,600 people in the room – the members of the press, the Cabinet, the President and all the distinguished people attending – have an amazing experience. To me it’s fascinating how the White House correspondents, in essence, influence our minds with the words they write and the interviews they broadcast. It’s near-identical to what I do. I shape narratives in people’s minds when I do my shows and give them the illusion that I’m reading their minds and somehow getting inside their heads. And I’m aware it’s going to be aired live on TV for potentially millions to watch. There’s a tactile feeling to my shows, where anyone in the room feels they might be called up on stage – and when you’re at home, you don’t feel that. There are artful methods to make viewers feel like they’re a part of it as well. That introduces a lot of complexity on my end to make sure the cameras capture it.
I’ll be telling more jokes than I normally do because the dinner is meant to have a comedy element. But I’m not there to roast people. I will poke a little bit of lighthearted fun, like I usually do at my shows, at all sides: the right, the left, the center and everyone in between. I am apolitical. I know why I was hired and it’s not to make people feel uncomfortable. It’s not to separate people or call them out in a certain way. The idea is to unite everybody in a sense of wonder and amazement.
When I found out in January they wanted to book me, my first reaction was, “Is this a mistake?” Maybe an intern is a huge fan and they’re going to phone back and say, “Sorry, we called the wrong person.” I thought they always booked a comedian. Then I heard through the grapevine that they were specifically looking not to have a comedian this year because they want President Trump to show up. With comedians in the past, he’s found it a bit too inflammatory and the roasting is not to his taste. It must have worked because he is attending.
The weekend before the dinner, I will have run the Jersey City Marathon. I expect the whole time – hopefully around two hours and 50 minutes – I will have been thinking about nothing else. I won’t have had my phone, I won’t have had anyone bothering me, so it’s actually the perfect spot to rehearse every part of my act. As crazy as that sounds, I need to run a marathon to prepare properly.
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