"People don't brag about going up a grassy slope," says Penn Jillette. "They brag about going up Everest."

That sentiment—that nothing worth celebrating was ever found in moderation—animates everything the juggler turned magician turned occasional pundit does.

Jillette has been known as the "larger, louder" half of the magic-and-comedy duo Penn & Teller for three and a half decades. Back in the 1970s, the pair were upstarts, fresh off a stint as part of a high-concept three-man stage act they called the Asparagus Valley Cultural Society. They were armed with an obsessive belief that practice makes perfect, and that conviction served them well: Their show, which started at L.A. Stage Company, made its way to Broadway and is now in residence at the Rio Hotel in Las Vegas. Along the way, they spent eight seasons hosting Penn & Teller: Bullshit!, a Showtime series in which they debunked myths and misconceptions from a decidedly libertarian perspective, and had cameos in everything from Sabrina, the Teenage Witch to Dancing with the Stars. Jillette also faced off with Donald Trump on The Apprentice. His magic competition show on The CW, Penn & Teller: Fool Us, just finished its third season.

Even before he was famous, Jillette had no interest in fitting in. He claims to have spent his childhood mouthing off at school and incessantly honing his juggling skills. A product of the Ringling Bros. and Barnum & Bailey Clown College, he later did time as a street performer in Philadelphia hurling knives for pocket change. At 6-foot-6 and "obnoxiously loud," he would have been hard to miss: A 1989 New Yorker profile characterized his hairdo as "a sort of frizzy ponytail and another fistful of hair tumbling over his forehead," adding that "he wore clear polish on all but one fingernail, and that one was painted red."

Jillette retains his distinctive manicure but is now lacking some of his trademark mass. Down significantly from his top weight of 330 pounds, the performer has baited headline writers everywhere into variants of the "magician makes himself vanish" joke. Indeed, he beats them to the punch in the title of his recent book on the subject, Presto! How I Made Over 100 Pounds Disappear and Other Magical Tales (Simon & Schuster). The secret to his weight-loss success? Realizing that, with food as with everything else, moderation is no virtue.

In October, Jillette chatted with Editor in Chief Katherine Mangu-Ward about his gastronomical, philosophical, and political views. Whipsawing between the profane and the profound, he described a variant of libertarianism driven by first principles, made the case for why porn actors and The New York Times are ultimately in the same business, and explained that sometimes it's harder to drop 30 pounds than three times that much.

Reason: You're a skeptic—you've built a career by being skeptical about conventional wisdom, religion, and traditional magic. How did that influence your approach to diet?

Jillette: I'm a libertarian. My political beliefs are way outside the mainstream. My religious beliefs are way outside the mainstream. My musical tastes, my theater tastes, my book tastes are way outside the mainstream, and yet I was eating fucking pizza and hamburgers. It's very odd that the one area that I chose to be the most typical American possible was food and diet. And once I got sick enough, my doctors said that I should consider getting stomach band surgery, and all of the sudden I realized I could be weirder. And I realized that not only am I not good at moderation, but I also simply don't respect moderation. If you're good at moderation, I don't like you.

When you say that you had to get fat enough before something radical was allowed—the same is true in the medical field, right? Essentially, we wait until people are dying before we let them try new drugs and medical devices on their own recognizance. Is that a fair analogy?

Yeah, I think it kind of is. But I mean, what you let other people do is pretty different from what you let yourself do. I would pretty much let other people do whatever the fuck they want pretty much all the time. For me…I'm not able to just do stuff sensibly. I tried for years and years and years to do weight loss with what I call the New York Times grown-up ways. Have a smaller piece of salmon. Have a piece of protein about the size of a deck of cards, and skip dessert. Be vegan until 6 p.m. All the weird-ass things that grown-ups are supposed to do. Exercise a little more.

There's nobody that's good at moderation who I even like or respect. People don't brag about going up a grassy slope. They brag about going up Everest. I realized that the only way that I can accomplish anything is if it's hard. Things that are easy to do, I don't do. There's just no sort of psychological desire to do that—I just don't enjoy that. So when I called up [food science researcher Ray Cronise] and said, "Can you help me lose 30 to 40 pounds?" he said, "Why don't we lose a hundred?" And I said, "Can we do that easily?" And he said, "No, it will be really hard. You'll love it."

When Penn & Teller are working on a new bit, and one of us comes to the other and says, "This is a really easy bit, we'll be able to do this easily, people will love it," the other one will go, "Fuck off, I don't care." We were doing easy stuff 30 years ago. We're doing hard stuff now.

I have been a teetotaler all my life. I've never done recreational drugs. And for some reason when someone ordered wine for dinner it was very comfortable for me to go, "Fuck off, I don't drink your stupid fucking wine." I don't listen to the Grateful fucking Dead. I don't need your fucking joint. And yet with food, it was like, "Oh, we're all eating pizza? Let's all have pizza!" The line that kept going through my head when I lost a hundred pounds was, "To live outside the law you must be honest." Everything comes down to Bob Dylan, and it fits in so well with the way I live now. I like being outside, and I like being a little different.

And I think [libertarians are] just OK being idealistic. We're OK being laughed at. You have to be OK if you're a libertarian with people like Bill Maher and Sarah Silverman calling you a fucking idiot.

When you read the news or maybe when you look at your Facebook feed, aside from the election, what are stories that jump out at you?

What I can't understand is watching people that I know well absolutely tick off every single libertarian principle and then scoff at [libertarianism] and hate it. Gary Johnson has said this over and over again, but everybody [we know] is fiscally conservative and socially liberal. And somehow they just want to say, "Well, of course that's right, but it just won't work." And it just amazes me.

It also amazes me—there's this thing that supporters of a candidate do where they believe their candidate is lying to win in ways that they agree with. I mean, as Bill Clinton flew to Arkansas to make sure he could put a person with mental disabilities to death, that week my anti–death penalty friends were saying, "Well, you know Bill Clinton is definitely against the death penalty, but he has to do this to get elected." And you go, "Wait a minute, what?!"

What is the political development in your lifetime that has affected you the most, personally?

Jesus, that's a real tough one. I think politics has gotten better. I tend to think that everything gets better. I always go back to the late '60s, early '70s, when my dad was my age: Our president has gone insane. The National Guard is shooting students at Kent State. We're involved in a war that will never end. It's an immoral war.

And now, at least as of [October 2016], we have a president that is sane and who is kind and who has very few scandals. We have an economy which is doing pretty well.

The best development in the private sector—I guess you can argue if it's private sector completely—is computers, the internet, communication.

The Gutenberg press created the United States of America. The idea that we're going to allow the press to have power, and people can read. You don't have the United States without that technology. And it seems to me like the internet is a much bigger change than the Gutenberg press in every single way.

"Not only am I not good at moderation, but I also simply don't respect moderation. If you're good at moderation, I don't like you."

The guy who more or less invented the web browser, Marc Andreessen, says that once the current technological revolution—smartphones, tablets, wireless internet—are in the hands of a billion extra people, "it is hard to believe that the result will not be a widespread global unleashing of creativity, productivity, and human potential."

I was one of the people talking at [the Massachusetts Institute of Technology] in the early '90s about how computers were going to change things, and I was one of the nuts that was making predictions that were much too optimistic—and I wasn't even close to what the reality was. [Reality] turned out to be so far beyond what any of the nuts thought.

I couldn't predict that juggling would get better. Juggling took the biggest jump ever because of the internet, and only because people could see videos of other people doing stuff. That's all it did. A brother and sister in Russia, when they were 12 years old, got the internet and became the best jugglers in the world. And they would never have juggled other than that.

That's something you can't predict. You can predict pizza delivery. You can predict drones. You can predict all that shit. You can't predict stuff that has nothing to fucking do with computers getting better.

The problem for human beings has always been too little information. And I don't believe there is such a thing as too much information, but we have to learn to process it and use it, and that's crazy.

A seminal moment in modern American politics is the day that The Daily Show's Jon Stewart goes on Crossfire and starts yelling at Tucker Carlson and Paul Begala, "I'm the entertainment. You're supposed to be serious!" Is the hybridization of entertainment and politics ruining everything?

I have a definition of art which protects me from this question. My definition of art is anything you do after the chores are done, and in that definition of art, Ron Jeremy, Picasso, and the mall Santa all have the exact same job. I believe there is one show business. So I don't really think there is much of a difference between a newscaster and a stand-up comedian in terms of what their job is.

Jon Stewart is playing the trick of you're supposed to do this and I'm supposed to do that, and the this and that are reality and entertainment. But the this and that are really just two different kinds of show business.

The newscasters should be held to the exact same standards as [comedian] Amy Schumer. With Amy Schumer we ask, "Is she interesting? Is she funny? Is she delivering the thing that we want from her at this moment?" I would say the same thing for Meet the Press. I would say you're not supposed to be funny, you're not supposed to be making things up, you're not supposed to be talking about the guy you went out with last night—but you are supposed to be giving us as consumers what we want. What we want out of you is a feeling that you aren't distorting the facts in giving us this information.

So you know, I disagree very strongly with The New York Times, but I read The New York Times almost every day. Because I trust The New York Times to deliver the kind of entertainment they promised me. And the kind of entertainment they promised me is that they won't lie about certain things, and that they will cover certain things, and that they will give me a well-rounded view of certain things that's within my vocabulary and that's in my style, and the length of article that I want, and all of that. So I would argue that The New York Times is doing precisely what Jon Stewart is doing, but they're just delivering for a different audience.

You did a show years ago about how ineffective prohibition is when it comes to immigration. In your worldview, is it about the moral gesture or is it the practical side that matters?

When I talk about the death penalty to people, there are a zillion pragmatic arguments to make that the death penalty is more expensive, that you could make mistakes with the death penalty. I try to never use them, because I believe that as soon as I use them, I have dropped what matters to me. Because those arguments are disingenuous. To say, "What if we put an innocent person to death?" I am then telling you that if you can promise me we won't put any innocent people to death that I'm somehow OK with that, and I'm fucking not. Killing people is wrong. Government shouldn't fucking do it. End of story.

I mean, if you can convince me right now on the phone that you can eliminate all marijuana, eliminate all LSD, eliminate all heroin, keep it out of the country so that people can't do it, and you can do that without using any violence—if you make that argument, am I then in favor of drug prohibition? I still don't think I am. If you told me here's a way we can keep all Muslims out and that will stop the terrorism, I don't think I can make that deal.

So I don't think there is a pragmatic argument. There is only the moral argument. I realize that's an incredibly black-and-white, stupid position that I don't think anyone agrees with me [on], but I can't find a way around it. So every issue becomes moral to me. I've never smoked marijuana in my life. I don't want to smoke marijuana. But I can't find any way that it's my right to stop you.

"My definition of art is anything you do after the chores are done, and in that definition of art, Ron Jeremy, Picasso, and the mall Santa all have the exact same job."

It's very compelling to describe it in that way, and yet frequently I see in your work—especially in Bullshit!—and in your conversation semi-pragmatic arguments cropping up. So is your stance that we can talk about the practicalities also, but let's be clear, what matters is the moral argument?

I hate the verb works. I hate it in art, I hate it in politics, I hate it in morality, I hate it all across the board. If someone tells me that they have a joke in their show and it works, I automatically hate that person. I want to know what their joke means, what they're trying to do. I don't want to be Charlie Chaplin, stumbling around until something gets a laugh. I want to be Buster Keaton going, "This is what I think in my heart is funny. This is what I want to do."

So with libertarianism, I find myself really often on Real Time and in other situations where people say, "You people think the invisible hand is going to fix everything and capitalism will give us utopia," and I always say, "I never said that." I don't even know if free markets work. There's that word work.

It just seems like it's not my right morally to do anything different. People say if you legalize drugs, you're going to have a lot more junkies. And then the other side says, Oh no, no, no, we will have fewer junkies [and] they'll be treated better. I don't know! I just know that if you don't have the right to put whatever you want into your own body, you're not living in a free fucking country. Simple.

So yeah, the pragmatic arguments are discussed, but my hope is that every time you've seen me make those, I've made them under duress.

Last question: When are you going to be replaced by a robot?

Well, in a lot of ways I already have been, right? I mean, isn't Netflix a robot? Aren't people choosing to see other entertainment besides live entertainment? Is there any way you can describe a TV image as anything other than a robot? Certainly the one person in the studio doing the act is a person who is employed. But certainly every other image that gets sent around is a robot.

And what we've found out, shockingly—and no one ever believes this [although] it's always true—is that radio did not put musicians out of work. Televisions did not put entertainers out of work. The internet sure shook up musicians, it's sure shaken up movie makers, but it still seems that job is there. If you want to talk about technology in the broad sense, the people who are reading my book right this second have replaced me with a robot, you know? There was a printing press that did that. I didn't have to scroll it out in front of them or say it to them. People are hearing my book on tape right now.

On cassette tape, I'm sure.

It was reel-to-reel I had in my mind.

But that shows the silliness of that argument. I watch these people argue about trade deficits and how all our jobs are going overseas. Our jobs didn't go overseas; they went to robots. We're arguing horribly about, what is it, 30 to 50 thousand jobs being lost in coal mining and we can't absorb that? Well, within five years, and I am making these numbers up, of course, but 1.8 million truck drivers will lose their jobs [because] right now as we speak there is an 18-wheeler self-driving across the country. That job is going away in about five years, and I don't think the government can stop that. I don't think legislation can stop that. Luddites have never won, ever. They drag their feet, but they lose.

So I've already been replaced by robots. The whole 20th century was about replacing me with robots. The 21st century is about replacing cars with robots, and that's freaking tough.

Anything else to add?

Drive fast and take chances while you still can.

This interview has been edited for style, clarity, and length.