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Penn Jillette on Donald Trump, Hillary Clinton, and Why He's All in on Gary Johnson

The libertarian magician also reveals how he lost over 100 pounds in a few short months and why Bob Dylan is his hero.

(Page 3 of 11)

GILLESPIE: Talk about—I mean you were on two seasons of Celebrity Apprentice with him.

JILLETTE: I did two tours of duty.

GILLESPIE: And from what I understand, the turning point of your relationship with him is when you discussed or described his hair as being made of cotton candy made of piss.

JILLETTE: I said it looked like. I didn't ever claim it was made of piss. Looked exactly like cotton candy made of piss. I'm not sure that was the turning point. The turning point actually…In those wild times of no sleep and pretending to be part of something that is not really happening. I mean, we're co-workers on a television show. He's not seeing if he's going to hire me. He has no job. The places he could hire me—the casinos that he has that have showrooms—he put into bankruptcy.

GILLESPIE: Right.

JILLETTE: He no longer owns them. So, he can't hire me, plus I have a job, so that's all completely fake, right? But during the time, it's not Stockholm syndrome, it's actor's playhouse. You get yourself—it's an improvisational, five week improvisational show in which you've decided that he is the boss and you are the employee, and you do that—

GILLESPIE: So this is like the Stanford prisoner experiments?

JILLETTE: A little bit, a little bit. More like that than like entertainment. So during that time, I know Donald Trump's lying about a lot of what happens, but I also know that I'm also not correct because everything gets jumbled together. But there was a time when they asked me while I was still on the show if Donald Trump ran for president, if I've support him. And I said absolutely not, and I believe—and this may be the most damning thing you'll hear me say about Trump—I believe I liked him more than anyone else who was on that show. During that time I said I would not support him for president. Now, I get a call instantly—instantly!—from the powers that be, not Trump himself, saying, "No, no, no. You must support him as president." They say "It's going to come down to you and Trace [Adkins], and he's going to want to know that you both support him for president." And I said, "Well, I don't" And they said, "Well, you have to because he's trying to—he's looking at the big picture here." And I go, "We're on a television show."

So, I was told when I said I wouldn't support him for president that I would not win, and if you watch the final show—and don't, why would you—he says, "You're being judge on the quality of your ice cream, the quality of your final presentation, how much ice cream you sold…" He gives a whole list of the criteria. And then he says, "Penn, you did the best ice cream. You did the best—" And he checks them all off that I've won every category. Oh, by the way, Trace wins.

Now, the Walgreens people were very upset by this because they wanted to sell my ice cream and do a whole thing. And NBC was upset by this. They're both so upset as a matter of fact, that they gave money to my charity kind of under the table, so I actually ended up making more for my charity than Trace did.

GILLESPIE: Wow.

JILLETTE: Because of kind of guilt money going in. They were very upset. I was not because the rules of this show are that he decides who wins, and there's no other little, you know—as a libertarian, we care very much about the rules. We really do. And if you and I are playing the game, and I have decided when I go in that whatever you say goes and you say something, I'm not allowed to say, "That's unfair!" There cannot be no unfair. I would also like to say about Celebrity Apprentice that… I am a terrible, terrible chess player. I'm horrible. But I can sit here with you and tell you what the rules to chess are. I can tell you what the rules to Texas Hold 'Em are. I can lay those out to you. I did two full professional runs of Celebrity Apprentice and did very well, and did as well as you can do and still be a failure, and yet I can't tell you what any of the rules are. *laughs*

There is not a game being played.

GILLESPIE: Is that what you—I mean, would a Trump presidency, which ultimately is unlikely, but is that one of the things that worries you about it? It's like, we would be in an America with no clear rules, although he would get to decide them.

JILLETTE: Not going for a joke and just trying as hard as I can to tell the truth… I think he doesn't really have strong convictions and sense of right and wrong. He's not really, really smart. He's not stupid, you know. He's not a dumb guy, but he's not smart like presidents are smart. We make jokes—Everybody's makes jokes except me about George W. Bush not being smart. He's smart. He just is. Obama's smarter? Probably, sure. Obama's smarter than Clinton? Probably. Almost certainly. But they're up here, you know, and if we're talking about it, you know…You're wherever you are, but you're not smarter than Obama, you know. None of us are. Even the smart guys you know aren't there. And Trump isn't one of those people. He's not someone who when you're having a conversation with him—I probably listened to him talk for, I don't want to exaggerate, but probably eight or nine hours. A monologue of Trump. And I can't think of one thing he said that I went, "Oh yeah!"

Now, try to think of someone in your life that could talk for eight hours—Now, be it it's on TV and it's to be chopped up and put on there, I'll give you that. He's not trying to be particularly profound, though he seems like he was. That's not true for Obama. I don't think Obama could talk to you for fifteen minutes about any subject without you saying either "I didn't know that," or "I never thought of that." Undoubtedly, both of those more than once. And isn't that the minimum you need from a president? 'Cause if Trump were to become president—which I think is so unlikely that it's insane, but if he were—the powers of the world crush him. He doesn't get anything done.

I mean, Obama, a good man—I think a wonderful man who, I think, we disagree with, but a wonderful man—was completely boxed in and able to do very, very little. Clinton, who really understands the game is, I think from—this is a cynical way to think I don't like to think but—thinking cynically, Clinton is probably more dangerous than a Trump presidency because she will actually get stuff done.

GILLESPIE: What worries you the most about Hillary Clinton? What is she going to get done that really freaks your shit?

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  • The Fusionist||

    He made the extra pounds...disappear!

  • The Fusionist||

    Oops, he used that joke in his new book.

  • paris1||

    Man, I had to turn this off halfway through. Is he on cocaine or just wildly over-caffeinated!?

  • Florida Hipster||

    I prefer fat Penn.

  • adampeart||

    Me too. And fat Newman as well.

  • SparktheRevolt||

    Someone can feel free to correct me, but I believe he has stated he doesn't do any drugs of any stripe, caffeine included.

  • ||

    Correct. He's mentioned it a few times, like on one of the "Bullshit" episodes.

  • $park¥ is totally a Swifty||

    Am I the only one who thinks there's something off about Penn? He seems like a decent guy, and generally honest, but there just seems to be something off. And I don't think it's anything to do with him being a carney.

  • Rhywun||

    All showmen seem that way to me.

  • Eloh-Nroc||

    It's called being "High on Life"

  • lucius.junius.brutus||

    Penn, I love you, but obama's a good man? Someone who wants to use government force to take your property and give it to other people? No socialist is good.

  • mfckr||

    Penn is just signaling or something. It's stupid. I don't get it either.

    A lot of people I used to like are just fucking demented these days.

  • Lord at War||

    There's a reason (drink) that I prefer Teller from this duo- He possibly might have equally disgusting political views... but he keeps his mouth shut.

  • CE||

    He meant "compared to Trump" I suppose.

  • josh||

    maybe politically, but i don't think that's what he meant. it's possible to despise a person's politics and think they're not the devil

  • Suicidy||

    I go out of my way to tell people, even strangers on the street, that Obama is a communist guilty of treason a dozen times over and should be publicly executed. Some people don't react well. I guess you just can't please everyone.

  • SparktheRevolt||

    I've never understood the deification of Bob Dylan. Great songwriter but his voice is worse than nails on a chalkboard.

  • The Fusionist||

    But you forget one key point, which is mumble mumble mumble

  • Cynical Asshole||

  • mfckr||

    Dylan is okay in moderation.

    You don't really listen for the voice, obviously.

  • Tulpain't||

    I'm not a huge Dylan fan, but he's the most versatile and influential American musicial artist of all time.

  • SparktheRevolt||

    uhh...

  • adampeart||

    And what study discovered this find? Sounds like a textbook Rolling Stone cliche generalization to me. Hardly quantifiable.

  • CE||

    Not Willie Nelson? Tom Petty? Prince? Hank Williams?

  • ||

    Willie Nelson or Neil Young, easily superbates Dylan in this. Nelson is also one of the best fucking singers since Al Jolson.

  • freedomlover||

    You had to be there man....... :-)

  • Lord at War||

    That's what works... great lyrics and sounds like a strangled cat.

  • Mongo||

    You ever see pics of that beautiful, psychedelic Dylan mural by Kobra in Minneapolis, Penn?

    Easily found on Google images.

  • lafe.long||

    "You're not smarter than Obama... none of us are."

    Disappointing to hear Penn say this.

  • Cloudbuster||

    I'm surprised we can understand him with Obama's cock in his mouth like that.

  • freedomlover||

    Be fair guys. Honest and honorable men can disagree and still be respectful.

    I know some really intelligent lefties that I respect. But their political views frustrate me to know end.

    Part of the reason I respect them is because I can't convince them of the incorrectness of their political views. I'm just not as smart as they are. If I was, we'd all be in agreement.

  • freedomlover||

    no NOT know!

    I hate that we can't edit of format our comments here!

  • Chipper Morning Wood||

    I like your comment. It's sad when otherwise smart people are so blinded by their ideological hate that they can't even admit that Obama is a smart guy. You can think he is politically deluded and still respect his intelligence.

  • Jickerson||

    It's hard for me to say how intelligent he is exactly, but I wouldn't say he's done anything to make me respect his intelligence. I'm not impressed by credentials or positions, so that's not enough.

  • Deven||

    Obama is smart in one way, and that is manipulation. And he only seems better and more intelligent than others because he has no morality to restrain him.

    He is a classic snake oil salesman. It is incorrect to assume he is intelligent just because he "excels" in areas a decent person wouldn't tread. I'd put my own intelligence against him any day in learning new concepts or logic, and I'm 99 percent sure I would crush him as would most people on this board.

    Point being, even if he has a certain type of intelligence, it is the type of a sociopath seeking poweror zealot , not someone who actually contributes meaningfully to society by creation or application of good ideas. That type of "intelligence" can and should be discounted as lunacy and abject stupidity.

  • Azathoth!!||

    Obama believes in leftism, in socialistic economics and in ideas like critical race theory.

    When faced with the reality that these are gargantuanly stupid ideas, he clings ever tighter to them.

    Thus, by definition he cannot be a 'smart guy'. He can aspire to idiocy by abandoning his beliefs entirely. Then, and only then, can he begin to become smart.

  • ||

    I ain't impressed by somebody that can't even string a coherent sentence together, hain't never said anything that can be broken down rationally so far as I know, who's done every fucking almost perfectly wrong, and with such a weird fucking habit of mispronunciation. Obama sees like a nobody, really, somebody there to deliver lines written by retarded monkeys in jail. Trump, in contrast, is a genius, which I thought and think even when I completely disagree with him. Even his flurries of unintelligible drivel which he's started delivering now and then since his candidacy started are devilishly clever. And he carries it off like he knows what the fuck he's doing, not like he's some dummy just poorly carrying out his master's orders. Fuck, retrospectively Bush was a genius compared to Obama. F u forget, just go back and read some of his speeches way back, you know, the ones we made fun of for being so dumb. They're super-intelligent now, by contrast with Obama.

  • Suicidy||

    I'm smarter than Obama. Not exactly setting the bar in the stratosphere with that statement.

  • NealAppeal||

    Gillespie: And when I started as a professional libertarian 20 years ago...

    What is this professional certification of which you speak?

  • SparktheRevolt||

    Paid Koch shill maybe?

  • adampeart||

    Oh spare me.

  • Suicidy||

    Kochtopus!!!

  • freedomlover||

    He was just setting himself apart from us amateur libertarians. The one's who don't work for Reason.

  • Lord at War||

    Being a professional whore is a bitch. I'm thinking even Weigel would say, "He's a crazy fucking leftist"...

  • Chipper Morning Wood||

    [scribbles something on an old piece of cardboard]

    Here you go, Neal. Welcome to the club.

  • ||

    Is it just me or is Penn a thick stache and cigar away from Groucho impersonator?

  • Lord at War||

    Penn has that "saggy skin" of someone who has lost serious weight- Groucho always kept it tight...

  • BambiB||

    I like a lot of Dylan music - but I saw Dylan at an Amazon.com show some years back and he reminded me less of Shakespeare than Blind Melon Chitlin. https://www.youtube.com/watch?v=mAw-3ERSIIY I don't know if he was drugged out of his mind or battling Alzheimer's or what. I walked out on the performance. You would have had to pay me to stay.

  • josh||

    i love what he said about dylan, and i appreciate him. however, i still side with the beatles. i would argue that they're just as authentic, but i've always been a sucker for artists that can combine commerce and art in a way that entertains and elevates us. great interview to listen to.

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