Penn Jillette Wants to Talk It All Out

The outspoken magician/comedian/writer talks to Cracked about leaving behind Libertarianism, why he’s worried about the future and how Trump is even worse than you think

Penn Jillette has a large, framed French-language poster of Renaldo and Clara behind him. Most people wouldn’t know what that is, but as a Bob Dylan fan, I do — it’s his largely forgotten, widely panned 1978 film that he wrote, directed and starred in. Only real Dylan obsessives talk about it, and Jillette is one of them. I’m speaking to him over Zoom — I’m in Los Angeles, he’s in Las Vegas — and when I mention the poster, it makes him smile. 

“It’s funny: I was at the Dylan Center in Tulsa and they asked to interview me about Dylan, and they got the cameras all set up and stuff,” he recalls. “And I said, ‘I’m a little taken aback because I’ve never done an interview that didn’t mention Dylan — but this is the first time I’ve been asked to talk about Dylan.’” The singer-songwriter is one of his heroes, and Jillette is tickled that I’ve brought Dylan up rather than him having to for once. “I bring in Dylan to explain everything,” he says.

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Turning 69 in March, Jillette not only worships Dylan but in some ways has tried to emulate his career. Both of them grew up in middle-class families, both of them became showmen, both of them have done a little bit of everything. The world knows Jillette best from his long-running magic/comedy duo Penn & Teller, but he’s also written books, acted and spoken out about political issues. He’s been on Broadway, and his latest television program, Penn & Teller: Fool Us, is now in its 10th season. 

Teller famously never talks during their routines, leaving Jillette to be their spokesperson, and in real life, Jillette talks a lot, too. I knew going in that he has opinions on everything from Taylor Swift to religion, but during our hour-long interview he never came across as a know-it-all. Rather, his views were often offered modestly, complete with disclaimers or self-deprecating jokes. He thinks a lot about a lot of things, but he’s not sure he’s right about any of them. That’s where talking comes in for Jillette — it allows him to try a rough draft of a stance that maybe he’ll later refine. In other words, he’s someone who can change his mind — like when he recently renounced Libertarianism after long being one of its most public champions. 

As we head into this election year, I was curious how he was feeling about the country, Joe Biden, his former Celebrity Apprentice sparring partner Donald Trump and the general direction of things. But we also discussed magic and comedy — which, he argues, can help explain politics. Penn Jillette knows he doesn’t have all the answers, but that won’t stop him from asking the questions.

This interview has been edited for length and clarity.

You’ve said that, as a boy, you weren’t into magic — you were into music. But what comedy albums were you listening to?

The first record I remember buying with my own money was the Smothers Brothers. They were everything to me — everything. And from the Smothers Brothers, we’d go to the Monkees — from the Monkees, we’d go instantly to Zappa, Velvet Underground. It was only a lack of talent that stopped me from being a musician — the passion was certainly there. 

I had an odd relationship with comedy — I was too pretentious and highfalutin for comedy. My family was very funny. I always made people laugh — it was always very easy for me, but they were always laughing at me and not with me. When I was in high school, I wanted to be the great existential writer — and I’d write stuff and it would constantly have funny stuff in it. I was drawn to Lenny Bruce and National Lampoon. I was obsessed with the fact that comedy could have a deep, deep meaning.

Obviously, if you’re starting out listening to the Smothers Brothers, that interest in a deeper meaning in humor must have been there from the jump.

That was really important to me. It was actually a difficult learning thing for me to realize that being funny was okay. Even the Stooges, I think that’s essentially about friendship among outsiders — it’s about love and the different manifestations of love. But I was going to move to France with my girlfriend and be a beatnik existential writer —  she broke up with me, I was very upset, I said, “Fuck you,” and went to Clown College. (Laughs) And that’s all you need to know.

There’s so much talk about A.I. replacing artists. Are you worried? 

Every single time something comes along, people (trash) it. When writing first came along, people said it would ruin our memories — and, of course, it did, but we got other stuff out of it. Recording, they said the same thing — John Philip Sousa was against recording because it would stop live music. Then he went on to make a lot of money doing it. Movies were going to ruin live performance — television was going to ruin the movies. And all of those things are true — every single one of (those fears) was completely true. But so what? 

I hope that A.I. isn’t a different thing. It may be — friends of mine who are very smart scientists have some trepidation about it. 

What are their concerns?

Not worried about artistic stuff at all, but worried that if you have A.I. doing all of air traffic control, one mistake…

My buddy Piff the Magic Dragon, he (uses A.I.) for magic tricks — “What would Piff the Magic Dragon say if he were performing this trick?” — and gets himself a first rough draft. If you have incredible fear of the blank page, and if you’re the kind of person that likes to fix things rather than generate from zero, you can have that. “First draft” is perhaps too strong — pre-pre-first draft. (Teller and I) have tried it for a couple of things — we needed to generate some full Biblical stuff, and we tried it, and it turned out we were better than it was. But that’s just one data point — that doesn’t mean anything. But it is plagiarism — it just simply is.

So, if it’s not A.I., what do you worry about?

Without being overly dramatic — but, I think, being accurate — there’s a small chance, but still real non-zero chance, that we’ve destroyed our country with monetizing hate and monetizing aggression and monetizing outrage. What makes you the most money is outrage and hate. 

I’m beginning to think that the whole MAGA movement, it’s possible we can blame that on fiction — it’s so exciting to have that turnabout in a movie where you find out that there’s a deep state. I certainly feel the pull for that — so much of trying to live our lives to do it right is tedious. And truth is very tedious. Trying to figure out how a certain insect interacts with an environment in the tundra is a lifetime of work — whereas saying that Hillary Clinton has a pizza place where she’s blowing young boys in the basement is no work at all. 

Einstein comes up with this idea E = mc² — a profound, powerful, mind-blowing idea — and he has to work forever to make people understand that and to share that reality. Woodward and Bernstein are pretty sure the president of the United States committed crimes, and they work their asses off to try to prove that. But if you’re deep in the MAGA movement, you can just type that Biden went to China and set up a secret nuclear arsenal, and you get this incredible amount of praise with seven-minutes work. Trying to get the news cycle to look as much like 24 seems to be the goal. 

Part of your public life involves debunking and demystifying — you’re interested in presenting the truth. Do you get depressed about living in a world where there are so many charlatans? So many people who just lie and lie? 

We can argue forever about gun control — whether that’s a good idea or a bad idea, including what the framers thought — but if we can’t agree that the shootings happened, then we can’t talk. I don’t think we’ve ever experienced a time in human history where there wasn’t a shared reality, even if that reality was false. I’d rather everyone believed in Christianity than what it’s turned into.

We should always be striving to agree on what reality is. A bunch of people have decided that it’s easier and more fun to not worry about that part of it. Einstein didn’t just want to run around saying, “E = mc²” — he wanted as many people as possible to share that reality. Woodward and Bernstein wanted people to share that reality. 

What we do in live magic, it’s constantly dealing with that subject. Recreational epistemology is what stage magic is — we play around with that. And if you want to get heavy about it, you can say that every magic show is an exploration of how we determine what’s true. 

Is that how you feel about the magic you do? Is that its purpose?

I do, but only a little. It’s not one of the Top Five things people are experiencing. When you want to talk pretentiously and be self-important, you’re always going to throw that in — I’m not sure it’s true, it’s certainly there. There’s a wonderful argument (that) you can’t really make a moral point in art because you’re working on a different level from that, it’s a different idea. Does 1984 really make a point? 

And yet, with all of this doom and gloom, everything is getting better by every metric we have. Things are getting better if we don’t destroy the planet with global warming and if Donald Trump doesn’t blow things up or Putin blows things up — those are the biggest “ifs” anyone’s ever said. But fewer people are starving. More girls are educated. Fewer people die at the hands of other people than ever in history. Those are big milestones. And some people argue — and they might be right — that art was part of that because the idea of reading a novel and putting yourself in someone else’s position, that (was) a huge deal. 

When you do a live magic show, (lying) does not enter into it. A live magic show in Vegas cannot include deepfakes. It cannot include false news. Everybody in our theater must agree on the reality — it’s the reality they’ve been agreeing on since they were in the crib. Gravity, time, objects, persistence — it’s all we deal with. You cannot do a magic trick of making another 10,000 people appear on the Mall during the inauguration if we don’t agree how you count people during an inauguration. There’s no trick.

Back in 2020, you offered newly-elected president Joe Biden advice on how to unite the country after that contentious election. How do you think he’s done as POTUS?

Biden’s done an incredible job. Accomplished almost the impossible. His stuff on Israel and Ukraine is four-dimensional chess. And what he’s done with the small amount that he has anything to do with the economy — the small amount he has to do with jobs — that’s all going well. I don’t think how well a president speaks off-the-cuff matters at all — I mean, it matters in terms of showbiz and it matters in terms of getting elected, which you could argue is all that matters. But it’s got nothing to do with the job.

Many have criticized his handling of Israel, arguing he has not done enough to protect Palestinians. 

He’s certainly not doing enough to help Palestinians. He's certainly not doing enough to help people over there suffering — which is also true for you, also true for me, true for everybody. I think he is in an actual impossible situation — I think that any action or a lack of action is wrong. It’s so far beyond what’s possible. 

Maybe the word that upsets me most is the word “we” — if you use the word “we,” and you’re not talking about eight billion people, fuck you. I have relatives who identify as Jewish, whatever the fuck that means, who say, “We were attacked first.” You live in Pittsburgh…

Every time violence is used, I think about Gandhi and Martin Luther King — we know that major revolutions are more successful if they’re nonviolent, which no one believes. Obama’s Nobel acceptance speech — and Obama is a zillion times smarter than me and more educated, so just assume he’s right and I’m wrong — but what troubled me was that he seemed to think that what Gandhi and Martin Luther King did was an anomaly, something that doesn't work. I don’t know how pacifism can work in Ukraine — I don’t know how it can work in Israel — but I sure wish there was someone thinking about it.

You mentioned you had a relative who identifies as Jewish “whatever the fuck that means” — what do you mean by that?

Because I’m in show business, many of my friends grew up Jewish — none of them believe in Judaism. Some of them think that there’s something cultural about being Jewish. And I tell them, “I know more about Lenny Bruce than you do. I went to Carnegie Deli more than you did. I have read as many people who identify as Jewish and are authors as you have. Am I culturally Jewish? I memorized the Carnegie Hall concert by Lenny Bruce that had a lot of cultural Jewish things in it.” 

Many, many years ago, a scientist at the media lab at MIT, we were working on something, and I asked him — and I don’t know why, this is not a question I’ve asked since — “Are you Jewish?” And he said, “No, no, I’m atheist.” And then he explained that his father had escaped from Auschwitz when he was eight years old. And he said, “My father has always stated he was atheist.” 

An argument that I hear once in a while from people who call themselves culturally Jewish is that their people have been persecuted and, therefore, they have to identify as Jewish to fight that — I go, “Don’t you want me on your side, too? Don’t you want everybody to be against anti-Semitism? Can’t everybody in Africa and Japan also be against it? Isn’t that okay?” I struggle with this tremendously, because I have such close friends and people who are relatives who don’t budge on that — if your mother was Jewish, you were Jewish, and there’s no way around that. 

I don't think I’ve seriously entertained (the idea of) there being a God. Yeah, I think that there’s a lot of wisdom in the Torah and use that — and also use Kurt Vonnegut and Joni Mitchell. A lot of wisdom everywhere taken in. Scholars of Judaism, I don’t give a fuck who their mother was.

Because of the Israel-Hamas war, even talking about this can bring up accusations that, by being critical of Judaism or Israel, it’s almost automatically anti-Semitism. Are you nervous talking about this?

Yes, I’m very nervous. But I want to be a little more high-minded. I’m not as nervous about being attacked for it as I am nervous about being wrong. As a good friend of mine said, “I don’t mind being called an asshole — I don’t want to be an asshole.” (Laughs)

I've promised myself over and over again that I won’t say, publicly, even to friends, anything about what’s happening in Israel because it is far beyond me. I have no understanding of what it feels like for an organized group to come into where I’m living and kill people that I know — I’ve never experienced that, so, “Shut up.” And, yet, to live in the world, we have to contemplate that a little bit.

What I’m getting from this conversation is that you think, yeah, maybe you should shut up, but you’re a curious, thoughtful person and you want to talk things out loud to test things — to test your own thought process.

It’s that same thing with magic — there’s that shared reality. I want to talk to people about what anti-Semitism is — and, obviously, anti-Semitism in Israel is very different than anti-Semitism in the U.S., and they're also related. This is damning myself beyond belief, but I have to constantly be reminded that anti-Semitism exists because it’s such ancient history to me — and I know it’s happening right now. 

I don’t know why, but I’m just going to tell you how stupid I am. I’m good friends with Karen Russell, Bill Russell’s daughter, who’s a Harvard lawyer. Her father was a superstar in basketball, and she is my age-ish, she’s in her 60s. She talks about touring with her father as a basketball star and not being able to eat in restaurants and not being able to stay in hotels. She’s telling me this — she’s saying this to a man who’s 68 years old and has lived in the United States and supposedly knows how to read — and my jaw drops. It’s so easy to say that we’re all one world and that there shouldn’t be anti-Semitism, there shouldn’t be racism — it’s so easy to be lovey-dovey and peacenik. But I say this without any qualifications: I’ve never experienced any of that (hatred). Never. So every time I’m making an argument that has anything to do with race or misogyny or anti-Semitism, I want to say back to me, “Wait a minute, Penn, you grew up cis male white in Massachusetts — I think you need to shut up.” 

That is the argument you could always do to me and will always work because it’s always correct. How can I relate to someone who, as an eight-year-old, is told they couldn’t eat in a certain restaurant because of their complexion? There’s no way to understand that intellectually. 

For so long, you identified as Libertarian. What changed?

I completely have not used the word Libertarian in describing myself since I got an email during lockdown where a person from a Libertarian organization wrote to me and said, “We’re doing an anti-mask demonstration in Vegas, and obviously we’d like you to head it.” I looked at that email and I went, “The fact they sent me this email is something I need to be very ashamed of, and I need to change.” Now, you can make the argument that maybe you don’t need to mandate masks — you can make the argument that maybe that shouldn’t be the government's job — but you cannot make the argument that you shouldn’t wear masks. It is the exact reciprocal of seatbelts because if I don’t wear a seatbelt, my chances of fucking myself up increase — if I don’t wear a mask, the chance of fucking someone else up increase. 

Many times when I identified as Libertarian, people said to me, “It’s just rich white guys that don’t want to be told what to do,” and I had a zillion answers to that — and now that seems 100 percent accurate.

So how do you identify politically? 

Well, let’s go to empirical evidence: I’m going to vote Democrat, maybe that’s all you need to know. I will not vote for a third-party candidate. I believe all the clichés, I believe they’re true — I believe that Trump and MAGA might make the United States unrecognizable enough that it’s not a beautiful place to be. 

I said to anybody who asked me, “No matter how bad you think Trump is, he’s worse.” I was living on the streets for a couple of years, and I stayed in biker clubhouses and I was in jail — I was sleeping rough, as they say, and hopping trains. In all that time with people who are on the fringes of society, I never met anybody that I noticed with two qualities that Trump has — someone that never made a joke and never appreciated music. I’m defining “joke” perhaps a little narrowly — I don’t mean, “You’re fat,” I don’t consider that a joke, even if Trump laughs at it. He never made a joke — never appreciated a joke that I ever saw. And you’ll notice that all his stump speeches, jokes (are) conspicuous in their absence. Obama made real jokes — stand-up jokes. Biden is not as sophisticated, but he knows what a joke is. Nixon certainly knew jokes. Carter certainly knew jokes. (George W.) Bush, one of his closest friends was Kinky Friedman. Clinton certainly knew jokes. I never heard (Trump) laugh at a joke or make a joke other than “You’re fat, you’re ugly.”

What do you think that means that he doesn’t make jokes?

I don’t know but, boy, it does not seem good. I know the Goldwater rule that even professionals can’t psychoanalyze someone they’ve not been in a room with, but I never saw the slightest bit of empathy from Trump.

And empathy is connected to a sense of humor?

Absolutely. If I knew what I know now and I’d spent time with Trump, I would’ve taken a knife and cut my hand, just watching him to see if he'd wince. My guess is no. 

(Trump’s) basic idea that, in a transaction, someone wins and someone loses is the most deeply anti-American, anti-capitalist idea you can possibly have. The idea of winners and losers being said about capitalism is a gross distortion of what that’s supposed to be. The way Penn & Teller run (our) business is I want everybody to make money. When we do a show, I have many friends who are freaked out if the promoter makes too much money — (that’s) a “bad deal” — but I just go, “Fuck, I want every promoter that books Penn & Teller to make a million fucking dollars clear. Wouldn’t that be great?” I’m certainly not talking about the way blues artists were treated — I’m talking about me who gets paid very well, that’s a whole different thing. But Trump says over and over again someone has to win and someone has to lose, and the fact that that’s being seen as American and as capitalism, that is the most unpatriotic thing.

I grew up in the 1980s, and that was exactly what I was taught American capitalism was. How did you grow up where that wasn’t the America that you knew?

My dad was originally a jail guard and then retired very young, 50, to be a numismatist, a coin dealer. My dad became, for our small town, a successful coin dealer, which would put us maybe a little bit lower-middle-class, but very well off for my town. And I remember, over and over again, people would come and bring their coin collections to my dad to appraise them — they (would say), “Would you give me $200 for this collection?” And my dad said, “No, but I’ll give you $1,000." That happened all the time. I mean, think of it in pure self-interest — consequently, everybody came to my dad. So I have a huge distortion because, being 10 years old and going to coin shows with my dad and hearing him negotiate, that was the way business was done. If you were asking me, “Is that how the United States was in 1965?” — I don’t know, I’m sure there were assholes. I mean, Trump Senior was being racist and ripping off people that same day that my dad was saying that.

The people you describe as your heroes, like Bob Dylan and Tiny Tim, I consider them iconoclasts. It’s a lofty term, but do you think of yourself as an iconoclast? 

It’s a little like the term “counterculture.” When the Beatles are called counterculture when they have the No. 1 album in the world, it becomes insane. When Howard Stern is the most successful radio show, I don’t know how you'd call Howard Stern counterculture. You call Brother Theodore counterculture.

So where do you exist in the culture? You’re rich and famous.

You can’t claim to not have ambition when there’s a theater named after you somewhere. But I’ve actually met people who are ambitious. When I was on Broadway, I knew Madonna — she would keep moving the goalposts to (make things) harder and harder and harder for her. I remember reading that Elvis was heartbroken that some people in China didn’t know his name. The most astonishing one of these was Paul McCartney, who has said repeatedly that the Beatles weren’t really as famous as they should have been. 

My ambitions were always, I think, fairly level-headed. I felt I could earn my living like my dad, who went from jail guard in a small town to supporting his family doing something he really loved — that was my goal. And when people talk to me and Teller about success, the day we were paying our bills doing a magic and juggling show, I was done. 

It was always so awkward when we were on Broadway and people would say, “(Did) you always dream of being on Broadway?” The answer, “No,” comes off as so ungrateful and so unpleasant and makes your skin crawl — but it’s the truth. I never wanted to be in a Broadway show. I certainly never wanted a Penn & Teller Theater in Vegas. But I wanted to do this show. So whereas the Beatles were not as famous as they should have been, Penn & Teller are much more famous than they should be. (Laughs) And much more influential on magic than we should be. 

I guess what we’re really talking about is legacy.

I get completely creeped out when people talk about legacy or the future. It seems like it is misunderstanding the job. Larry Fine of the Three Stooges was appalled that they would show the Three Stooges shorts, one after the other, on TV because, in Larry’s mind, they were live shows — it was not meant to just sit there. 

What I am doing is creating ephemera, and I believe that’s not only okay, that’s part of what makes it beautiful. I mean, I am aware it’s likely that in 30 years someone who is deeply interested in magic will dig up recordings of Fool Us and have things to learn, but that’s not what we’re really talking about. That’s excavating a piece of pottery. 

Bob Dylan said he was a song-and-dance man, and I believe Bob Dylan really means that. The people that I know that know Dylan well say that when he says, “Don’t look back,” he means it. They say he’s the least sentimental person they’ve ever met — he finishes the lyrics to a song, he sings it, he throws it away. Now, other people pick it up and make hundreds of thousands of dollars — and it turns out he threw a lot of stuff in the box if he knew someone else would care about it, and that’s in the museum. 

But one of the things that’s so inspirational about Dylan is he goes out and does live shows — he bangs them out. Some of Dylan’s best songs are recorded so sloppily — he sees the song as something that keeps going. Thursday night is my next live show — I’ll do the show, and that thing that I’ll do is a different thing for that night. That’s our job.

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