Magician, comedian, and libertarian
Magic, Omarosa, and a single painted nail
Penn Jillette is an American magician, comedian, and author. And he’s also half of “Penn and Teller” – the duo have performed together for more than 40 years, with a 15-year run at the Rio Hotel & Casino… making them the longest-running and most beloved headline act in Las Vegas history.
Jillette is a libertarian and has stated that he may consider himself to be an anarcho-capitalist as well as an adherent to Ayn Rand’s Objectivist philosophy. He’s a fellow at the libertarian think tank, the Cato Institute, and has stated that he “always” votes Libertarian.
Here, Penn talks with Investor Hour hosts Buck Sexton and Porter Stansberry about magic, his time on Celebrity Apprentice, and how he came to be a libertarian…
PORTER STANSBERRY: I am one of your biggest fans. I am in awe of your ability to build a career in the entertainment business the way you have. I love the books that you’ve written. But the question I have for you to start with is all about your political philosophy…
How in the world did you stumble on to libertarian thinking and thought? What put you on that path? Because it’s such an unusual philosophy for most Americans, and a lot of people have never even heard of it. So how did you come to those ideas?
Penn Jillette: I didn’t come to them. They were brought to me. I was your standard kind of Hollywood liberal around the late ‘80s, early ‘90s, and I met a guy named Tim Jenison who I ended up making a movie about called Tim’s Vermeer.
He painted a Vermeer in a warehouse in Texas with technology that he rediscovered, that he – you could say invented except it’s pretty clear that that’s what Vermeer used to do his painting. And found out kind of, in at least one sense, what Vermeer was doing was not paintings but rather photographs.
So this very thing that makes me think that war is so rarely the answer is the same thing that makes me think that so rarely government control is the answer.
Way back when we first met, we were talking one night and he started talking politically…
And he argued with me for about two hours about what freedom really means. I think, strangely, or at least strangely to people who don’t understand libertarianism, as my peace with nature. What bothers me the most I think in general is the use of force and coercion. So this very thing that makes me think that war is so rarely the answer is the same thing that makes me think that so rarely government control is the answer. So I kind of came around to it with a friend yelling at me. And my peacenik leanings.
PORTER STANSBERRY: I’ve seen many libertarians yelling about the initiation of force before. That’s a common theme among us.
Penn Jillette: Yes. I really think, for me, it’s because I’m a coward. I’ve never hit anybody in my life in anger. It’s hard to believe I would even fight to defend myself. And I’m really against that. So I have to ask myself: What would I be willing to use force to stop?
And although I might not have the strength or the bravery, I would use force to stop a murder. I would use force to stop rape. I would not use force to build a library. And that, I think, in a nutshell is my libertarian philosophy.
BUCK SEXTON: Penn, what do you think about this anonymous op-ed in the New York Times? This is what everybody in D.C. is talking about. Have you read the op-ed?
Penn Jillette: Of course I’ve read the op-ed. And the smart money says Dan Coats, right?
BUCK SEXTON: Really? Because I was going to say: one, who do you think is responsible? And, two, what do you think of the message? It’s basically saying in summary that there is a group – he calls it a “steady state,” not a “deep state” – of senior administration officials that are trying to stop the president from messing things up because he’s so crazy.
PORTER STANSBERRY: Is that really that unusual? Because I have maybe 500 employees. And the same exact thing goes on right here. People always think the boss is crazy. And they think that for the good of the institution, they’re going to not do what they’re told to do. At our company we call it “stonewalling”… When I have a big radical idea that people think are risky, they just won’t do it. And they just stonewall me and hope that I forget about the idea that I had. And usually I do. That’s just how organizations work. It’s not a conspiracy.
Penn Jillette: It’s not a conspiracy and it is the way organizations work. I think, having spent a lot of time with Trump – and the editorial, in your summation, that seems right – when you read the actual details, where they disagree with their boss is more profound than you see in business. And their use of the word “crazy” when they’re talking about you is probably accompanied by an eye roll. When they’re talking about Trump, it may be accompanied by cold sweat.
And I think that is a profound difference. The people around Trump really worry that they have a mentally ill child who is the most powerful man in the world. And that is very different.
Having spent a lot of time around Trump, it is remarkable – I’ve never been around somebody who had no filter, no thinking, and no kind of sense of other people.
I think if you talked about a president who, whether we agree or disagree, was smart and sane like Bush or Obama – pick either one of them – even presidents we disagree with profoundly and think didn’t do anything like Carter were sane and smart. I’m sure the people around them did a lot of jiggling and nudging and manipulating to have them do what the employee thought was a better job. Having spent a lot of time around Trump, it is remarkable – I’ve never been around somebody who had no filter, no thinking, and no kind of sense of other people. It is really remarkable.
Now, in a reality show and show-business environment, that’s completely acceptable. We have found a use in entertainment for mentally ill people. Not only do we have people who have serious psychological problems, but also we cultivate those. There’s no doubt that we as a culture drove Elvis and Frank Sinatra insane. And we were OK with that. What we got out of that was someone very entertaining who spoke to our hearts. And we’ve certainly seen that – I mean, you certainly saw that with Richard Pryor. Many, many of our geniuses – Lenny Bruce – were put in a role that drove them crazy.
BUCK SEXTON: Is it fair to ask, Penn, if creativity has a bit too close a relationship with crazy?
Penn Jillette: I don’t know about that. I’m always a little bit skeptical when somebody – and many people do – try to consider their lack of prudence and their capriciousness and self-centered qualities to be part of their genius. Because you do have people who are phenomenally talented and at the same time incredibly sane.
I mean, Steve Martin comes to mind as somebody who is as sane as anybody you’re going to find and yet has a body of work as good as anybody you’re going to find. And you even saw that when Lou Reed got off drugs: very sane, hardworking. I’m trying to go for the people that you would think would be crazy. Debbie Harry of Blondie.
BUCK SEXTON: Can I focus you in on Trump if I could, Penn? I’m sitting down with your former contestant and colleague, Omarosa Manigault, tomorrow for an at-length discussion. What can you tell me about Omarosa?
Penn Jillette: Well, she texts with my wife fairly often. She has a wonderful relationship with my wife. My contact with her was as somebody who was playing a role, you know?
In wrestling it’s called the “heel.” You have the face and you have the heel in professional wrestling. And the face is the good guy and the heel is the bad guy. And Omarosa played a character with her own name that she considered to be a character that was a bad guy on reality shows.
‘We’re going to go in a room for three hours and I’m not going to be myself,’ at the end of that three hours, what do you think about who you’ve met? It’s difficult.
I have enough trouble just trying to present myself as honestly as I can that I’ve never been much of an actor. I’m not good at playing a role. So since she would say to me that who she was when I was around her was not who she really was, it was very difficult to get a picture of her. If someone says to you, “We’re going to go in a room for three hours and I’m not going to be myself,” at the end of that three hours, what do you think about who you’ve met? It’s difficult.
The question everybody wanted me to answer – especially Stephen Colbert, aggressively on TV – wanted to know if I heard Trump say the N-word. I never did. I don’t know if he ever did. It doesn’t seem like part of his culture.
And I don’t know what more evidence you need of Trump’s racism, unkindness, incompetence, and capriciousness than what we have without any inside sources, without anything anonymous, without anything underhanded. It seems like his incompetence is broadcast.
PORTER STANSBERRY: Before we go, one last thing. I heard that you leave one of your fingernails painted in honor of your mother. Is that true?
Penn Jillette: Yes. When I first started doing magic and juggling, my mom told me that I should keep my fingernails really clean and nice because people were looking at my hands.
So I grabbed her fingernail polish and I put it on my nail and said, “Do you mean like this?” in order to mock her. And I wore the nail polish in order to mock and horrify my mother through high school. And then as I got older and more successful, I would run my thumb over my finger with the nail polish when I was on Letterman or the Tonight Show or any of those shows just to let my mom know I was thinking of her at that second. And then my mom died in 2000. And now it’s I can’t say to remember her because I never forget her, but to honor her. I should say I’m quite a mama’s boy. I was very close to my mom.
And my daughter, who’s 13 years old, I heard her say recently to her friends that I do the nail polish because of her. And I believe my mother would approve.
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