"Conservatives and libertarians were always portrayed as the shrill and unhappy guys, and the left and liberals were always the people who are having fun," says Greg Gutfeld, host of Fox News' The Greg Gutfeld Show, co-host of The Five, former host of Red Eye, bestselling author, and Reason magazine intern reject.
"What you're seeing now is a lot more fun on the libertarian and right side than you've ever seen on the left."
Gutfeld sat down with Reason's Nick Gillespie to discuss his "ugly libertarianism," Donald Trump's love of Red Eye, why he was excited about the U.S. withdrawal from the Paris Agreement, and why Trump's comments on the campaign trail were best understood in the context of a Comedy Central roast.
The interview took place on stage at Freedom Fest 2017, an annual gathering for libertarians in Las Vegas.
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Audio post-production by Ian Keyser.
This is a rush transcript—check all quotes against the audio for accuracy.
Nick Gillespie: Hi everybody, I'm Nick Gillespie with Reason. Thanks for coming out. We're talking with Greg Gutfeld who most of you know as a ubiquitous presence on Fox News and the author of many best-selling books. I know him though and will open with this, we're going to talk for a little bit about various things but so you know Greg Gutfeld as the host of the opotamus Greg Gutfeld show. He's on the Five, he's the creator and the host of Red Eye.
Greg Gutfeld: Awe, a Red Eye fan.
Gillespie: Late invented Red Eye for sure, but I know you mostly as a failed intern at Reason Magazine. Can you tell us that story?
Gutfeld: Well, I don't think you can call me a failed intern because you actually never gave me the job, but I think when I got out of college one of the first places I applied to, I applied to maybe a thousand places and one of them was reason. I think it was, I'm trying to remember the name of the person on the rejection letter but I think it was Virginia.
Gillespie: Yeah, it was Virginia Postrel. This was, I think, even before I was in there.
Gutfeld: You were like 13 but you still have the same hair. It's insane. You can see Nick coming for like two days with that hair. It arrives first, but yeah, it was a nice form letter, very pleasant, very polite. Basically saying thank you for the letter, but no. I got used to that and by the way, this was back before you had the internet so when you applied for a job, as most of you know, you had a dot matrix printer and you had the newspaper and you just would sit there and go through the newspaper and it was a sign of desperation on how wide you would spread out the options. I'm going to be a novelist but I could be a copy editor or I could be a temp then all of a sudden you're at some place repairing lawn sprinklers, which is what I ended up doing for a while one day actually.
Gillespie: Is that the last honest job that you had?
Gutfeld: I'm trying to think the last, you mean outside of media?
Gillespie: You were also at Prevention Magazine, pushing pills, drug pusher.
Gutfeld: No, actually I was the Fitness editor at Prevention magazine.
Gillespie: Any Prevention readers out there? Just shout because I know you can't lift your arms above your shoulders.
Gutfeld: Terrible, terrible, but you know, the great thing about physical fitness is to conservative, libertarian practice in the sense that whatever you put into yourself, you can actually see the results. That are no affirmative action for abs and I've said that many times.
Gillespie: Wayne Allen Root, he has an honorary six pack because he went to high school with some people who had six packs.
Gutfeld: That might be the best joke of the night so we might as well just call it a day and leave.
Gillespie: Thank you. Greg, let's talk about-
Gutfeld: Very good.
Gillespie: … your TV work but also you're writing but before we get to that Freedom Fest is mostly libertarian. How many people out there call yourselves libertarian? Okay, and how many would say conservative? Okay, a fair amount. Liberals? Okay, not so many. You walk a line of Conservative and Libertarian, you've referred to yourself as an ugly libertarian, which by the way, an ugly libertarian can also be defined as a very handsome conservative.
Gutfeld: That is true. You know what? What is it LGBTQ? I'm Q, I'm questioning. You ask me any day I could be a libertarian or a conservative or a libertarian conservative because frankly, I don't know. I call myself an ugly libertarian because there are a lot of things that when I get into a conversation with an idea log, they go, "You are not a libertarian", and they get very upset because I'm a libertarian who likes to carry around a lot of guns. I think libertarian but I'm speaking metaphorically as a national defense. National Security, I believe if you want to smoke pot and have orgy's, you shouldn't worry about Sharia Law. You want to smoke your pot, you want to do your ecstasy, which looks like it may be legalized. No applause there, but you should applaud because it's amazing. I'm going off topic here, but anyway, my point is this-
Gillespie: I was going to say that you sound like you want to live in the world that R. Kelly is building for himself in basements across America.
Gutfeld: No, no. I have no idea what's going on there. I know is that in order to enjoy the freedoms that we want to enjoy, we have to be able to stop those people who want to attack our freedoms. Sharia Law is symbolic of that.
Gillespie: Because you don't really, Sharia law isn't really breaking out over the place, right? I mean, Fox News-
Gutfeld: It's happening in my apartment.
Gillespie: No that's just being married.
Gillespie: Okay, yeah, but I mean Fox News had a more strict code than most Sharia law communities under Roger Ailes. Wouldn't you say?
Gutfeld: I missed the first part of the question because I was-
Gillespie: I know, you're not going to talk about Fox News too much, right?
Gutfeld: Oh, you can ask me certain questions if you like, but not questions about my late boss.
Gillespie: Lou Dobbs, is he as good looking naked as he is on camera?
Gutfeld: Wow. Finally, get to the meat of this talk. Lou's eyes are so blue you can't tell whether he's wearing clothes or naked because you never look below his eyes.
Gillespie: All right, I'll buy that.
Gutfeld: His voice is so soothing, he can hypnotize you into anything. I often do his show and I'm on for an hour and I have no idea what happened.
Gillespie: He goes out, he has-
Gutfeld: He goes out, has coffee, comes back and I'm still there.
Gillespie: In your most recent book, How To Be Right, and I highly recommend this book because it's about argumentation and rhetoric and kind of convincing people and persuading people of your point of view almost regardless of the point of view although you are sympathetic to conservatives and libertarian arguments. Can you tell us about the origins of that book and you talk about how people like Trevor Noah or Jon Stewart or Steven Colbert, have been successful in kind of broadly pushing their world view on people? What is it that they're doing that a lot of people that you feel in the center or the right or the libertarian space are just failing at?
Gutfeld: I think that if we were having this conversation five years ago, I would give you a far different answer or before I wrote the book, which was the things that I felt were disadvantages that we weren't, we were always positioned as, I call it the Dean Wormer effect. Dean Wormer was the dean from Animal House and we're owed conservatives and libertarians are always portrayed as this shrill unhappy guy and the left and liberals are always the people having fun, so when you turn on the daily show they're laughing their having a good time and they're always portraying the right as the people who are unhappy. Who aren't having a good time. Then, because of their ideology, it's incredibly simplistic, its basically based on emotion. Liberalism is emotion and how can you, if you are against Obamacare or single payer, how can you want babies and old people to die? It's an emotional, simplistic argument that really does work for younger people and older liberals who think like younger people.
They have it easy. What I was trying to do with my book was figure out a way and it was based on my monologues I would do on The Five. How do I persuade people on specific topics and there are two things that you try to do. You try to simplify it so that people understand it and its like designing a product. You've got to design a product so you know how to open that door. Everybody's locked into a door, because they can't figure out how to open it. That's a lot of conservative, libertarian ideologies. It's like how do I get into it?
Every time I wrote something, it was like how do you get into it? How do you explain it and how can it be fun? The idea for it came because everybody kept asking me how I wrote my monologues. How do I think about things? I try to think about it as though I'm slightly drunk and trying to explain something to somebody at a bar. Like if you've got to talk about, I don't know, foreign policy. Here's the problem, here's what we need. You open up your brain to a way of thinking that you didn't open up to before. Now I say that its changed because I do think that what your seeing is a lot more fun on the libertarian and right side then you've ever seen on the left. It has shift.
The shift is unbelievable to me. I mean, the smarter people, the more clever people, the funnier people are on our side and the angry people are on their side. When you go on Twitter, it is amazing, like all the comedians that you liked and I won't mention their names. They're not funny anymore. They're on Twitter. They are in complete, absolute hysterics. They are now Dean Wormer. They are now the miserable people. It is so refreshing and whether you like, despise, love or hate Donald Trump, and I went through every one of those emotions last year. He made it okay for a lot of people to say "What the hell." I saw this when we did a debate on campus. No, we went to the debates. I don't know if it was Hofstra. It was the first time I was ever on a campus where there were students marching for conservative stuff out in the open. I go, "We never would have done that at Berkeley."
Gillespie: Well, you went to Berkeley.
Gutfeld: Yeah, yeah, but I had never seen people that were so openly saying what they had felt and they were conservatives. They were libertarians. They weren't liberals and what happened was nobody challenged them because we operated under the assumption that we were outnumbered, outgunned and we were going to be humiliated. In some respects, at were you worked, you could be, but in this case, Trump had tested the waters and a lot of other people started jumping in. I mean Breibart was probably the revolutionary behind it, but you know, what happened was, all of a sudden these people are doing things and nobody is stopping them. That's the lesson that I think a lot of people have learned that like, you know what? What were we scared of?
Gillespie: To focus on Trump a little bit, on the very first Greg Gutfeld Show, which airs at 10:00 PM on Fox News, Saturday night, please watch it. Donald Trump was in the first episode of the Greg Gutfeld Show. How did that happen? Then talk a little bit about the different stages of grief you've gone through with him and where do you think he is right now?
Gutfeld: It's a strange thing because, there are Red Eye fans out there and Red Eye fans are very unique. They think for themselves. They are often up late, they could be doing meth. I don't know.
Gillespie: The smart ones are making it.
Gutfeld: Smart ones are making the meth, yes. I get a phone call from Donald Trump. I don't when this is like 2011, 2012, I don't know. To tell me how much he loves Red Eye and it's not BS, he knows the show inside and out. I'm going like, "Okay, here's this guy that watches, like Donald Trump watches Red Eye." He doesn't just watch it, he understands it. Then he just complimented me and that was it. He would call a couple other times about Red Eye, specifically about Red Eye and just talk about what was on it. He knew Andy Levee was and Bill Schultz was. I mean, you've got to be into a show to know what we're doing, especially a cult-y show.
Gillespie: The talking New York Times-
Gutfeld: Yeah, the talking New York Times. I mean, like, 70% or 80% of the people here don't even know what I'm talking about, but he did. What? Who? Oh, my brother Gunther, anyway, I should stop listening to that guy. Anyway, I got to know him casually through that. I did a speech for Allen West in Florida in Mira Lago. I flew back on his plane. I spent some time with him and I asked him to do my show and he said "Sure." That's all it was and so I went over and talked to him about running for President and we joked about me being his press spokesman and all this other stuff. It was a fairly, benign, fun thing but he said this thing to me, which I'm paraphrasing and I said, "So, you're going to do it, aren't you?" He said, "Greg, believe me, if I do it. Oh, it's going to be amazing. You are not going to see anything like this ever."
Gillespie: Well, he was right about that, yeah.
Gutfeld: I was going, like, he always says stuff like that so I was like, "Yeah, whatever." Then, he came down the escalator and in my pod. I'm doing The Five and Red Eye and a pod is like where everybody works for my show and we are like going, "This is incredible." We know that this is some kind of phenomenal thing. He comes down an escalator and we were laughing. This is the greatest thing ever. He gets up there and he makes that, he kind of fumbles his immigration point by saying rapists and killers.
Gillespie: Some of them, I assume are nice people.
Gutfeld: I'm like on The Five going, "I'm so happy." Then I was like, "Damn, why? Why can't you?" It's kind of been a love/hate thing. When you're on the same page with somebody for a lot of things but he doesn't articulate it the way you wish he would and it often forces you into a situation where you have to explain it. I refused to explain. I wasn't going to be a Trumpsplainer. I coined that phrase on The Five. I'm not going to trumpslain it. If he says it, you've got to hold him to the fire. I would often do that, but what I realized was that I was making a series of mistakes when I was looking at. I think I was right on a lot of things, but I think I was wrong about the context. I kept placing Trump in the wrong context. He wasn't in politics. He was in a Comedy Central roast.
Every day for him was getting up and saying, for example, I really didn't like the thing he said about John McCain and I made it very clear that every single day on The Five that he owes an apology for John McCain when he said that you know heroes don't get caught. I just thought it was a disgusting thing to say about military. Then I was thinking about what if this was a Comedy Central roast and John McCain was the roastee and everybody gets up and Donald Trump starts in, "Yeah, everyone here is calling him a hero, but heroes don't get caught." That would have killed. People would have said, "Oh my god, he's kidding. It's a joke. It's a burn." That's what it is. I started thinking like, he grew up in a world where all he does his burn. This is how he talks. He's a real estate guy who deals with contractors. This is how he talks and he was mad that those guys had been calling his people crazies so they were calling, I think-
Gillespie: Wacko birds?
Gutfeld: Yeah, wacko birds.
Gillespie: That was the libertarians. He was mad at Justin Amosh and Rand Paul.
Gutfeld: Yeah, exactly and so his response was to come back at them. When I started looking at it in the context of this is a new phenomenon, I started to understand that-
Gillespie: Having a Comedy Roast honoree be the President of the United States.
Gutfeld: Exactly. This is new. We haven't had this since Coolidge.
Gillespie: I was going to say an actor who co-starred, who got second billing to a chimp? Yeah, we're good with that, but this is, we're in unchartered territory.
Gutfeld: Exactly, exactly.
Gillespie: Do you think, is it a good thing for Trump and the way that he talks about stuff, is it good that he is President? Or is it irrelevant? I mean, are you happy with his substantive performance as opposed to his rhetorical flourishes?
Gutfeld: There are some things that I really, really like. I mean, he's rolling back regulations, which I think is very important. I was very happy.
Gillespie: Although I will point out and this is where the detail usually matters. He actually, his budget raises regulatory spending by 3% more than Obama's did. You can peel away certain things but you know-
Gutfeld: I would argue that he is closer to Rockefeller than Reagan. I think that he is a centrist and he's done something to the ideologies of both parties. They are not the same anymore. There are some good things and bad things. Things I don't like is all the protectionist talk. I'm a free trader. That stuff bugs me. I understand when I talk to people about this they go, "No, this is a stance that he is taking to get a better deal." He's just saying we're not going to do the deal right away. I get that, but that stuff makes me nervous about taxing people to pay for the wall. I don't like that stuff. I also, have to say, the climate change thing, I didn't think he was going to do that because I thought that his daughter was going to talk him out of it, and I thought it was great and I loved it.
I loved how it affected people. It just, there were people having nervous breakdowns and I was sitting there talking to them and I was like, "you do realize if you're an environmentalist, you should be applauding what he did because it's a terrible deal." If you believe that in 100 years we are not going to exist, this isn't going to do anything for you. It's a hundred trillion dollars they are estimating for moving celsius 2/10ths of a degree and they are not even sure that does anything. It's a scam and Trump was, I thought was brilliant about this in that he sidestepped, he sidestepped the science. He was like, "We're not going to talk about the science." It's a bad deal. If you come back with a better deal, we'll talk about it. Everybody's going, "Oh my god, it's the end of the earth." No, you're an idiot. It's just a lousy deal, its as simple as that.
Gillespie: Trump, you mentioned before, Trump has enforced the kind of derangement syndrome on MSNBC to a certain degree on CNN, not all of them. The New York Times, et cetera, Washington Post, do you think that Trump truly will use you as an emissary of Fox News, which is the biggest cable news network and is generally favorable towards Trump. Is Fox being suckered into that position of Trumpsplaining in a way that is whether it's good or bad for the network, its bad for the general discourse about politics?
Gutfeld: It goes back to I believe the definition of fair and balanced, which is that you just when you feel the boat is tipping this way about everything, you immediately move over here to get the boat right. When people go, "Oh, Fox News isn't fair and balanced" because they're watching a show, a specific show and there might be three people that are all in agreement, there's no dissent in that panel. You go, "You call this fair and balanced?" You have to take a step back, step out of the network, step out of mainstream media and you see that the boat is like this and all they are trying to do is this.
Having said that though, we have a lot of almost every hour with maybe the exception of one, has a healthy dose of Trump skepticism. Then there are different slices of it. There's the type, "He can do no wrong", which I think is a mistake. I've always argued for the guardrails of criticism. If you really want someone to do well, you got to criticize them because there's nothing worse than a Yes Man. A Yes Man will drive you to your grave and I find it nauseating when it was under Obama for eight years and I don't like it now. You've got to have some kind of healthy skepticism no matter what. There are things that really bug me about him but I've accepted certain things. Part of the acceptance came the day that he was inaugurated.
Gillespie: At that record crowd. The biggest crowd ever.
Gutfeld: The only crowd larger was in the meeting with Donald Trump, Jr.
Gillespie: That's right.
Gutfeld: That is such an obvious joke. That's an obvious, hacky, joke.
Gillespie: We've got a few minutes left and what I want to ask you and I think its pre-political or pre partisan certainly, pre-ideological.
Gutfeld: That's a lot of pre's.
Gillespie: Yeah, no it is. I wish I had a good line for that, yes that's right.
Gutfeld: What was the question?
Gillespie: I really don't know. Where am I? I feel like Admiral Stockdale.
Gutfeld: Uh oh, your dealer's here. I want the stuff that makes us smile. Oh okay, not the candy.
Gillespie: It's okay, it's okay.
Gutfeld: What was that about?
Gillespie: Frank Sinatra, Jr has been released by the kidnappers so everything is going to be all right. We have about a minute and a half left but then we're coming back. This is what I hear, but we're going to have a special guest levitate in. Very quickly-
Gutfeld: Is it Gallagher?
Gillespie: You are a big fan of punk music or just very expressive music. How did that infuse your early concepts of self and the way, even when you were writing for health magazines and things and certainly for the Felix Dennis Publications that you did. How does that come through in your work and how did that help form you?
Gutfeld: I think that people who were originally attracted to punk rock in '77 or in '76 even with The Ramone's or you can go even earlier with the New York Dolls and Richard Hale. You were the outcast. In your head you were the outcast or you felt that whenever you were around people that agreed, everybody agreed on one thing. They all liked the same music or they all liked the same TV show. You always felt this weird resistance. I think when punk rock came out it was frightening to me and I felt like the effect that it had on other people as I liked it made it special to me. I think that kind of like, so almost every job I've taken and everything I've done, I've always had that weird, I don't know, it's a path.
It just tells me when, whether you're among a large group of pro-Trump people or a group of anti-Trumpers. When I went into Cal, it was a perfect example, when I got to Cal, I was a liberal. In six weeks, I was done because I was going, "My god, when people all agree with each other, it's really dangerous. It's really scary stuff." You can see that with right wingers. There's something about group think that is frightening.
Gillespie: Almost daily you reduce both Juan Williams and Dana Perino to tears on The Five. Your kind of the Johnny Ramone of The Five.
Gutfeld: I try and I try to make each segment approximately two minutes and 30 seconds.
Gillespie: Okay, I was going to say Bob Beckel than is the DD Ramon-
Gillespie: … Of The Five.
Gutfeld: Oh, poor Bob.
Gillespie: I believe we now have a special guest so we are going to vacate the stage for a couple minutes.
Gutfeld: All right, I'm being evicted.
Gillespie: No, thank you very much.
Gutfeld: Thank you.
Gillespie: Yeah, this is-