Conan O’Brien recently spoke with us about his Catholic upbringing, writing for The Simpsons and his 25 years in late night while spreading the word about Conan, the new half-hour version of his TBS talk show. During that conversation, O’Brien also answered a question about Donald Trump, who was a frequent guest on O’Brien’s show beginning in 1997 and through Trump’s years hosting The Apprentice on NBC — which was also O’Brien’s network home. Trump took part in bits like “Secrets” and talked about his dating life over the years. But one moment stood out to O’Brien. Here is his story, in O’Brien’s own words, edited for clarity and brevity.
The first time we had Trump on our show, I asked him a question that I’d always wanted to ask someone who proclaimed to be a billionaire: “How much money do you have on you right now?” He sort of said, “I don’t know, I maybe have some.” I said, “No, no, what do you have?” Then he stuck his hand in his pocket and he clearly found something. I saw his face change, and I could see that he didn’t want me to know what it was. So I reached over and I was like, “Come on, come on.” I made him pull it out — and it was a condom. He said, “Practice safe sex everybody.” He was in-between marriages at the time.
He was pissed. He was really mad. I went to commercial. He stood up. I don’t think he said goodbye to me, and he walked over to my producer and said, “That’s the last time I’m gonna be on this fucking show. He humiliated me in front of everybody.” He stormed out. Cut to me seven more times [over the years]: “Ladies and gentlemen, Donald Trump!” He got over it, clearly.
He would shoot bits for us: “Can we get Nipsey Russell to come shoot something? He’s not available? Well, then try Donald Trump. Donald will do it.” Anyone who would do that, and then is the leader of the free world, is not going to make sense to me.
Growing up, you always put the president up on a pedestal. The minute the president is someone that you know, you think, “That guy can’t be president. I know that guy. I saw that guy steal towels at the gym. He can’t be president.” That’s the feeling I think a lot of us have.
I read a piece recently, maybe in The Onion, about how Trump is allergic to humor. To really have a sense of humor, you have to be able to laugh at yourself. You have to be able to see the human condition as absurd. Our funny presidents have always been able to see the inherent absurdity of it all. John F. Kennedy served in the Navy and saw how fucked up the Navy brass was and how badly things were done. His illnesses as a kid helped educate him that life was a crapshoot and inherently ridiculous. I think that gave him a great, witty sense of irony. Lincoln famously found himself to be hideous and was the first one to make fun of himself, our most self-deprecating president.
I think all of that is anathema to Trump. Trump’s superpower is constantly believing in the infallibility of Trump. Humility is a weakness to him. Having performed two different White House Correspondents’ Dinners and seen Clinton and Obama sit there and laugh at themselves, I don’t think Trump can do that. Look at how Dana Carvey was able to lampoon George H.W. Bush and then George H.W. Bush invited him to the White House and they became friends. That was someone who was comfortable enough in his own skin to be mocked.
It didn’t surprise me when the White House Correspondents’ Dinner went away. I thought, “How can Trump participate in any of this?” It’s really interesting because he did the Al Smith dinner with Hillary Clinton just before the election. I was impressed: There were four minutes up top where he was pretty funny. I think people had written some stuff for him. He was poking a little fun at his marriage. Then, I thought for a second, “Wait a minute, maybe he is able to.” Then he went right into, “But, we gotta remember, Hillary was wrong. Also, this is wrong, and I was right about this.” He couldn’t do it. It’s not in him. Then once he was president, there’s so much insecurity about the size of his inauguration crowd. I think he’s racked with insecurity every day. I think what’s tragic is what he doesn’t understand is that it’s a strength. If he was able to come out and say, “You know what? Yeah, I screwed this up. I’ve made some mistakes,” he would really surprise people. In a way it would confound a lot of people who don’t like him. But he can’t do it.
Here’s another clip of Trump appearing on O’Brien’s show, taping a bit called “Secrets.” Trump tried to improvise by dumping water on his desk, but the joke fell flat. “All of us were stunned,” says O’Brien. “That’s not humor.”