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Andrew Heaton joins the show to talk about how the world of comedy tackles politics.

Aaron Ross Powell
Director and Editor
Trevor Burrus
Research Fellow, Constitutional Studies

Andrew Heaton is a comedian, author, and political satirist. He’s the host of “The Political Orphanage” comedy and news podcast, and scifi deep dive podcast “Alienating the Audience.” He’s a frequent Reason TV contributor and hosted the popular webseries “Mostly Weekly.”


Andrew Heaton is a comedian, author, and political satirist. On this episode he explains how, in the last four years, many funny & talented individuals have stepped away from comedy because they do not feel it is an appropriate moment in time to make jokes. But, the power of laughter is often underestimated.

Further Reading:

The Political Orphanage, Podcast hosted by Andrew Heaton



00:07 Trevor Burrus: Welcome to Free Thoughts. I’m Trevor Burrus.

00:09 Aaron Powell: And I’m Aaron Powell.

00:11 Trevor Burrus: Joining us today is Andrew Heaton, award‐​winning comedian, contributor to Reason, former congressional staffer and former primetime television writer. He hosts the policy and comedy podcast, The Political Orphanage, and the science fiction podcast, Alienating The Audience. Welcome to Free Thoughts, Andrew.

00:28 Andrew Heaton: Hello, thank you very much for having me on, Trevor and Aaron, nice to see both of you, hear both of you.

00:31 Trevor Burrus: So we’re recording this, everyone, ’cause this will come out after the election, but we’re recording this a few days before the election.

00:40 Andrew Heaton: Howie Hawkins has not yet won. It is still a cost up between Donald Trump and that other guy, Joe Biden.

00:47 Trevor Burrus: Yes, exactly. And so the listeners in the future will know things after the civil war starts and the riots in the streets, and we’ve become a Mad Max type of society when this actually comes out, but at this point in time, as a comedian, should we be laughing now or is everything just horrible?

01:05 Andrew Heaton: I don’t think there’s ever a period where it’s inappropriate to laugh, including funerals, like if I were… When the streets are rubble and smoke, and your producer Landry has become a warlord and is walking around with heads on pikes, even then, I do not think that levity… Levity negates gravity, or levity negates the seriousness of a situation. In all seriousness, if I were commissioned to give a eulogy, which I assume is the proper terminology for a eulogy, I would still incorporate jokes into that. I do not think that you need to shut down there. And it’s been a… One of the just incredible sad things about the last four years as a comedian is so many otherwise funny, talented people have wilfully decided to quit being funny.

01:58 Andrew Heaton: And something that I encounter in the field that I work in, and that a lot of other comedians that I know, is we’ll be making jokes and someone will go, “I just don’t think it’s appropriate right now, when we’re so close to fascism to be laughing.” And I’m like, “You know, if literally you can’t go vote because you’re laughing, then maybe.” But the rest of the time, I am rather stoic about these things, and I maintain a position that you ought to keep a sovereignty over your emotional state if you can. We should all be empathetic, we should all care about the people around us, but you should have a certain degree of equanimity. And so when horrible things are happening, and there are a lot of horrible things happening, try and stay happy. The world is no better. The world is no better for you being angry and sad and pissed off.

02:45 Andrew Heaton: The Dalai Lama, that guy? He’s really sad about Tibet. You look at that guy, he seems real jolly, so… Yes, anyway, keep laughing.

02:54 Aaron Powell: Is this move towards seriousness and now is not a time for laughter driven just by we’re inches away from fascism, or is it a broader cultural shift too towards laughter or jokes have become increasingly inappropriate or perceived as such? Like, so if you laugh at the wrong times, it’s offensive to people, and it feels like there’s this other drive, this other kind of anti‐​comedic drive, which is that we shouldn’t make jokes that might offend.

03:27 Andrew Heaton: Yeah, well, I think there’s two phenomenon happening and one phenomenon is that when a Democrat is in the Oval Office, a lot of Republicans go crazy and think it’s the end of the republic. When a Republicans in the office, a lot of Democrats go crazy and think it’s the end of the republic. So that’s always gonna happen to some extent, that happened to some extent when Obama was in office that, I suspect, given your position of endorsing liberalism and thought that is not necessarily mainstream within either major party that you guys are probably never really enthusiastic about whoever’s in the AFL office, I feel that way.

04:03 Andrew Heaton: There are a lot of people that only feel okay and have never gotten used to it when someone from their party is sitting on the iron throne and view American politics increasingly like 17th century British politics, of like a Catholic must sit on the throne of England. But I think the bigger issue that you’re alluding to, Aaron, that I think you’re correct about, is that America didn’t actually become secular. I realize that that is the standard talking position and that is where academia is charting out of, America has become increasingly secular and less religious, I don’t think that’s the case at all, and I say this as a secular individual.

04:43 Andrew Heaton: I think that everybody up in New England that used to be a Puritan kinda just became woke. There has been this pendulum effect of the people at parties going “You’re not allowed to say that” has shifted. In the ‘90s, that was mostly conservatives. If we were to go back in the wayback machine, in the ‘90s, you had to tiptoe around family programming and the vice president’s yelling about Murphy Brown being a single woman with a kid, and the religious right is censoring things and like if you’re gay, maybe you’re gonna get kicked off of the writing staff because that’s gonna offend sponsors, so back in the ‘90s, the people that were freaking out were generally conservatives, and like The Simpsons I think is a great example of this, of The Simpsons today, completely blase. However, when it first happened, and I think you guys… You look younger than me, but I think we might be in the same age cohort.

05:44 Trevor Burrus: We generally are, yeah, we remember.

05:46 Andrew Heaton: Right? So if you go back to The Simpsons, when that first started, that was quite controversial, and I remember my parents going like, “Oh, I don’t know, they say butt,” and all these things. And then like Homer would, I don’t know, Homer would have an episode where he’s like friends with a gay guy or something, and a bunch of conservatives would freak out, and then all of the liberals at the time, all the progressives would go, “Guys, it’s just a cartoon show, it’s just a big hole we shovel jokes into. It’s not a spiritual exegesis. You can calm down. Just enjoy it. Just sit back,” right? That was the ‘90s, that has now flipped, where today the new moral majority is the woke people. The people that are going, “Guys, just calm down, don’t worry about it,” tend to be libertarians and conservatives, and it tends to be the very spiritual, very, very, very emphatically correct kind of re‐​microwaved Victorians, that’s coming from the woke side of things, where there’s certain words you can’t say, there…

06:45 Andrew Heaton: And it’s not like you can’t say it because it’s a bad idea. It is a blasphemy, it is an affront to the universe, and when we get into that zone where we’re at now, where if I say a particular thing, it’s not just that it’s improprietal or it might be offensive, but I have literally brushed against the cosmic fabric of integrity. That has a stultifying effect on humor and a stultifying effect on looseness, which tends to correlate with humor, and if we’re all kind of walking on eggshells and we’re afraid that we make one pithy tweet about Waffle House then our career is gonna be destroyed and the earth salted, then it has that effect. Yeah.

07:23 Aaron Powell: This story, though, the flip from the ‘90s to today, how does the political correctness of the ‘90s fit into that? Because I remember that being… And I was a teenager at the time, and so it’s hard for me to remember if it was serious or not, but there certainly was this strain of political correctness, and we had The Politically Incorrect Bedtime Stories book that was making fun of it that was this huge best seller. Was that different than what we’re seeing now, or was it like a proto version of what we’re seeing now on the left, because that political correctness was like a left kind of political…

07:52 Andrew Heaton: Yes, yes. Yes, I do recall that book that you referenced, and I do remember that being a rallying point in the ‘90s. I think the two phenomena that have accompanied that are, one, I think that it has become pervasive in a lot of different spheres. So in the ‘90s, you still had pretty much full rein at a comedy club and on a college campus, which I would posit are the two places that really ought to have full range of thought, where you could just kind of say whatever you want and nothing happens. That has… Comedy clubs, absent COVID, are still pretty much there. However, there has been a lot of encroachment, I think the fact that everything can be online, that everybody can be YouTubed has changed things.

08:44 Andrew Heaton: Back in the ‘90s, if you said something inappropriate at a steak house or something like that, that might be taken out of context or whatever, the likelihood that it was immediately gonna be videotaped and put on some website designed to destroy your life was unlikely. The other element that I think that has happened is I do think that the default state for human beings is one of religion, and I think that wokeness is fulfilling that. And I think it is further kind of amplified by the fact that absent a traditional community where religion in the United States is kind of everything, I know you guys talked about this on your last show with Steve Pittz about alienation and liberalism and so forth, I’m more on the Robert Putnam side of things of the more that traditional communities decline… We don’t go to Elks lodges, we don’t go to Rotary Club, all that kind of stuff, people aren’t going to church, synagogue, mosque, etcetera, etcetera.

09:44 Andrew Heaton: The only community left standing is politics, and so that gets infused into everything, and I think what would have been the zest and intensity people would have reserved for tent revivals and going to church is now all getting funneled into politics, which has now become not the engineering solution I have to help people or how best the machinery of the state should be run, it is a statement of identity, and this is how I commune with the world, and voting is an active sacrament, and I am… I am projecting my values through blah, blah, blah, blah. I find it exhausting. I’m still of the old‐​school liberal hold‐​out of like, “Nope, it’s just problem‐​solving and solutions.” I approach politics like engineering. But I think it has become, in answer to your first question, Aaron, I think that it has become increasingly religionized or spiritualized, and that accounts for much of the shift.

10:43 Trevor Burrus: On the question of offensiveness, especially in terms of comedy, it seems that there’s a war going on, as you said, coming from the left more, but maybe we’re forgetting, or some people never learned that there’s a value to being offensive. I’m thinking of people like Lenny Bruce or comedians like Richard Prior who would have been maybe arrested on stage, like Lenny Bruce, that there’s actually a value because it’s… Or even if you’re a comedian in the 17th century and you go up and you say something about the Catholic church or the Protestant church that maybe some things that need to be said, but you might be thrown in jail for it. So do you think that we should be more willing to embrace offensiveness as a general method of communication?

11:26 Andrew Heaton: Great question, and I am going to respond by pulling in the Nolan square, to the great joy of hopefully your listeners, who I… I assume you’ve talked about the Nolan square a couple of times.

11:41 Trevor Burrus: The world’s smallest political quiz, yes.

11:45 Andrew Heaton: Yes. So in the same way that I think it is reductive and obtuse to look at the political landscape in the United States and go, “Well, there’s a left and a right and that’s it. Everybody is either progressive or liberal,” I think is very similar to going like, “Well, everybody’s Catholic or Protestant.” I’m like, “I guess I’m a Buddhist,” and they’re like, “No, that’s just an extreme Protestant, or you’re just a Catholic who likes… ” But no, I don’t fit into any of these things. I think the culture war is very similar, and I would draw it… I would make an X and a Y axis and say that we have been really misinterpreting the culture war in that it is typically portrayed as left versus right, and that’s not it. It’s never been that.

12:22 Andrew Heaton: It’s never been progressive versus conservatives, that’s not the actual demarcation or the fault line of the culture war. The culture war is and always has been between pluralists and authoritarians. So if you wanted to make an X and a Y axis, imagine that you’ve got an X axis that’s how socially liberal or socially traditional you are. If you go further to the right, you want nuclear families, you’re skeptical of smoking pot, etcetera, etcetera. If you go really far right, you think gay people are sinners, etcetera, etcetera. You go really far left, you’re like doing threesomes at Burning Man, you microdose, etcetera, etcetera. That’s not actually where the conflict lies, it’s not along that spectrum.

12:58 Andrew Heaton: The conflict is that Y axis of pluralistic to authoritarian, and it’s the authoritarians that have a problem with anybody stepping out of line. Pluralists can handle that, ’cause pluralism is this idea of like, “I think you’re wrong, and that’s okay. I am alright with you existing and I can work with you and be neighbors with you while you are in a state of error,” whereas authoritarians have to rinse you back and make you fit into their paradigm. And within that matrix, Trevor, I think you’re right, there is a benefit to the gesture that can call out the craziness of a system. Now, I do think you can go too far, I’d say, along that kind of, let’s say, like authoritarian versus anti‐​authoritarian spectrum, you can go far enough on the anti‐​authoritarian spectrum that you’re just riling up people for your own amusement, you’re intentionally saying bigoted or bigoted or offensive content for its own sake, because you enjoy trolling people.

14:05 Andrew Heaton: I don’t think there’s any value to that, I think that you’re… You’re actually kind of damaging the social fabric, but that’s on the extreme end, right. Before you get to that point, Lenny Bruce is a very good example of somebody that is making fun of the stultifying atmosphere of the ‘50s and is bringing light to that situation. And there’s plenty of instances I can think of where having somebody kind of buck the apple cart can be very useful. And a lot of the time, particularly in humor, like we can do it in a way that nobody else can.

14:38 Andrew Heaton: There’s a wonderful TED talk by a guy named Chris Bliss, who’s both a very funny comedian and also like an expert interpretive juggler, which I won’t even bother trying to explain, but in the TED Talk, he talks about how if you argue with somebody, your adrenaline level shoots up, as does theirs, and your cortisol level shoots up, and that means that both of you are becoming increasingly less receptive to outside idea; actually, your memory declines too. Arguing actually is not a very useful method for distributing ideas. Conversely, if you’re making jokes, you can… If you and I are both laughing, we both get a dopamine kick, we get endorphins, and I have found as a comedian that when I’m on stage and I’m getting the audience to laugh, they’ll walk with me for the length of a joke.

15:27 Andrew Heaton: They might disagree with me, but they’re like, “Okay, we’re on board for the 35 seconds it takes you to set up and punchline this,” and you can relay interesting information there. When I started doing stand‐​up when I was in DC, the audiences were predominantly the Progressive Democrats, and I’m not gonna go into full stand‐​up mode, I’m just gonna relate the content to you, but I had a joke where I’d go, “You know, that’s great. I have a lot of Democratic friends, I like how open‐​minded Democrats are about stuff they already agree with,” and it would get a good laugh. Had I phrased that as like, “You know, I think you guys aren’t so much open‐​minded, you’re just pro gay, which is great, but you’re not really open,” like that wouldn’t have done anything, right? But when I phrase it as a joke, they were like, “Ah, okay, that’s true.” So yes, anyway, Trevor, I think that there is a benefit to having outliers who tell the emperor he has no clothes.

16:17 Aaron Powell: One of the axes it feels like culture has become increasingly concerned with, and this seems to fit into this discussion of offense, is power disparities, that there are certain groups that are privileged and/​or powerful, there are certain groups that lack power or aren’t privileged, and that offense becomes acceptable or not based on which direction. So to simplify, it’s the punching up and punching down. And so I wonder how much of what we’re seeing is not that it’s wrong to cause offense and not a rejection of that underlying benefit of offense of the counterculture outsiders making jokes to critique the stultified and often oppressive mainstream, but instead that what’s the counter culture and what the mainstream has shifted out from under the comedians, I suppose. And so now, what used to be punching up looks just like punching down.

17:18 Andrew Heaton: Yeah, there’s a lot to unpack there. The first thing that I’ll throw out is I’m familiar with the paradigm you’re describing of punching up versus punching down, that is a source of much discussion in New York comedy circles, particularly amongst improv, which, to get really nitty‐​gritty, there is… Actually, you know what, you guys would be perfect to describe this to, and I know your audience would get what I’m gonna talk about, so I’m not even going to try to… Stand‐​up comedians tend to be de‐​ontological in their ethics, whereas improv comedians tend to be consequentialists in their ethics, and so there is a flashpoint there. The consequentialists, the improv people are very concerned about punching up and punching down.

18:00 Andrew Heaton: And my retort to that, to borrow a line from fellow comedian and friend Joe DeVito, is, “I guess if you think comedy is about punching, I don’t.” Like, I’m an absurdist. If anybody goes and listens to The Political Orphanage, my program, when I do comedy on there, it’s in the vein of the Zucker brothers or Dave Barry or something like that. I enjoy, I think because I have swallowed this rational pill and my brain is so fixated on logical syllogisms, I very much enjoy and find relief in just going kind of crazy, you know, anchorman Dave Barry kind of humor.

18:40 Andrew Heaton: I’m not punching anybody, I don’t… You don’t have to have it weaponized. When you do go that direction, I become very suspicious of it very quickly. I think ad hominem, ad hominem logical fallacies apply to humor as well. The idea that I can’t make a joke because of my skin color I frankly find offensive. There is an increasing idea within the comedy world that we should have different rules for people based on race and sex, and I find that abhorrent. I am very much an old school, old school classical liberal when it comes to that of like, I don’t mind changing the rules, I don’t mind updating the system, but I do fervently maintain that we should all be abiding by that system, we should all have the same rules apply to us. So if we’re gonna make a rule, which I think would be stupid, but if we’re gonna make a rule that you can’t make jokes and use an accent, if I’m describing an encounter with the black guy, I cannot make a black voice. If we’re gonna do that, I think everybody should do that, like you only only talk in your accent.

19:46 Andrew Heaton: I would not endorse such a rule, but the idea that like, well, you’re Asian and so you can do these things and you can say these things, and I’m a white guy, so I’m limited to this, and you’re black, so you can say whatever you want, I don’t think it’s a way to go. And the other element there of the ground shifting from under comedians in terms of counter culture and culture, there is a really wide latitude right now, I think, for comedy that is not being explored, and that is making fun of moral certitude and making fun of people taking themselves seriously. And our culture is so… It’s not Orwellian, it’s Victorian. We are very Victorian right now, we are very, very concerned about proper etiquette and propriety and being respectable and saying the right things and doing the right things. We’re in that category. It’s rife for comedy. People on the left are not hitting it because they’re afraid to, and also they can’t, in the same way that very devout Christian comedians probably aren’t gonna make really funny jokes about the apostles engaging in fellatio or whatever, there’s too many sacred cows there, they won’t go after their own sacred cows.

20:55 Andrew Heaton: It’s not really coming from the right, partly because there just aren’t that many comedians on the right, but also because the temptation is so intense to go alt‐​right or to go really offensive and, you know, kinda drop the mic and walk away, that no one’s doing what we did in the ‘90s, which was like, look, I’m not gonna like really make fun of Jesus, but I am gonna make fun of you guys for taking Jesus so seriously and like do it in a way that we can still hang out. That venue is really not being explored right now, and there’s… For any fledgling comedians listening to your podcast, you could make a pretty good living, I think, if you figured out how to navigate that, where you weren’t being castigated as a bigot for obvious reasons, but at the same time, could figure out a way to poke fun at all these people that are really taking themselves very seriously.

21:43 Trevor Burrus: Well, that leads nicely to my next question, which is, given that kind of framework you set up, does that put libertarians in a better position perhaps to be comedians. And I think that you have seen a lot of comedians do make fun of the absurdities of people in power, and you can see, think of movies like Dr. Strangelove, which is not a libertarian movie intentionally, but has very many libertarian themes. I think that Veep has many libertarian themes, Yes Minister, like all these ones that make fun of people in government as sort of bumbling idiots, they play right into ours and everyone kind of agrees with it, which is fascinating.

22:20 Trevor Burrus: But you have people like Doug Stanhope, who is explicitly libertarian, who gets an audience by making these points about people in power. So do you feel that you have… You can combine that, your libertarian views with your comedy in a way that is beneficial with audiences, it resonates with audiences?

22:39 Andrew Heaton: Yes and no. Yes, I think you’re very correct that by virtue of not being on the left‐​right spectrum and by not having sacred cows in the fight that I have to avoid punching… That’s a weird analogy, but I think, I think I’m clear on it. You have more targets you can snipe at and less reticence to do so, and that is a benefit in that really, really devout people, whether they are Christian or they are woke, are gonna have fewer things that they can talk about and are gonna be more tip‐​toeing around them, so libertarians have an edge there. But the downside is if you brand yourself explicitly as libertarian, you immediately knee‐​cap your potential audience. Right now, in particular, as politics becomes the new religion, people are less and less comfortable exploring other viewpoints, even if it’s just humor, than they used to be.

23:42 Andrew Heaton: And if it’s branded as such, they’re very reticent to do so. So if I were to do… The Political Orphanage, my show, is largely temperamental, I am designing it for people that feel alienated from the two‐​party system and wanna solve problems, but I don’t… I’m not trying to infuse it with an ideological agenda. I have my own positions, but it’s not like The Raging Liberty Boner with Andrew Heaton or something like that, it’s The Political Orphanage, right? Were I to call it that, The Raging Liberty Boner with Andrew Heaton or something like that, it would attract libertarians, but it would also immediately staunch any future flow from moderates, Democrats, Republicans.

24:21 Andrew Heaton: However, when people have done that, of basically inhabiting a libertarian world view without putting it at the very front of what they’re doing, they’ve been incredibly successful. And the example that I can give is… Well, I’ll back up, like hanging out in DC circles, going to cocktail parties and occasionally to meetings with really wealthy donors for various things, a common refrain is like, “Why hasn’t there been a libertarian Daily Show?” And my answer is, “There is, it’s called South Park,” it’s one of the most gang busters successful programs in American history and it’s libertarian. Now, they don’t call it that for shrewd reasons, one, because I think that Trey Parker and Matt Stone predominantly, I think, just anti‐​authoritarian and just enjoy provoking people. They’re provocateurs, but they’re always taking swipes at both Republicans and Democrats.

25:13 Andrew Heaton: In 2016, I think they said that they asked Trey Parker and Matt Stone who they would vote for, and they said something to the effect of, “We’d vote for Johnson if we thought he had a chance,” something like that. So those guys, I have to say their humor is very libertarian, and I say that both in terms of their political orientation and in terms of the sort of heuristic window that they operate from. And it’s worked very, very well, for all of those reasons, but they’re kind of… Not duplicitous about it, but people don’t realize it. So like when I was living in New York, my roommates would watch Last Week Tonight With John Oliver, which is very progressive, not even progressive, but like British progressive, and then they would turn around and watch South Park and they would laugh at both and South Park would rip apart all of the stuff that John Oliver had just said, and they wouldn’t even really catch what was happening, that there were these two different viewpoints.

26:02 Andrew Heaton: So yeah, short answer is, I think that you have more opportunity and more versatility if you were approaching outside of the Republican or Democratic worldview, but you also have to be careful because if you wanna hang a scarlet L around your neck, you are going to naturally cordon off a certain audience.

26:21 Aaron Powell: Confining ourselves for a moment, though, to that Republican versus Democratic world view, it often feels like almost inevitably that there is an enormous quality gulf in comedy and in just art in general between liberals and conservatives, that liberals just seemed to be much, much better at all of this stuff. And so you can watch, as like a libertarian, I can watch a leftist comedian or a left of center show, and it can be The Daily Show or the Colbert Report, and it can be wildly funny, but every time conservatives try to do something like this or make explicitly conservative movies or whatever, it falls flat on its face. What’s going on there?

27:07 Andrew Heaton: Yes, there’s two parts to that question. The first part of like, why does the conservative Daily Show fail? What does that happen? There’s a very specific reason for that, and incidentally, if you have any really deep pocket billionaires that listen to your program that are like like, “Oh, man,” okay, I’m gonna give you the equation right now. It could be done and it will yet never be done. The reason that these always fail is that The Daily Show, when it started, didn’t set out on an ideological crusade, it set out on a comedy goal, and everybody happened to be progressive, and is evidence of that. I don’t know now, but the first 10, 15 years of The Daily Show, maybe still, but certainly at its inception, they had a rule that if there was a line that was written to provoke applause rather than laughter, it would be stricken. They were not going for applause, they were going for jokes, and that was the whole point, the whole point was just to be funny and have fun, and they happened to be progressive.

28:12 Andrew Heaton: And whenever conservatives and libertarians want to get in on this game, they approach it like agit prop and go, “Oh, man, wouldn’t it be great if we could trick the young people into understanding water rights or whatever, and we’ll just… We’ll sugar coat it with some jokes, we’ll hire a clown and we’ll have the clown render it palatable.” And people can sense agit prop a mile away, and it’s not gonna work. And what would work, if anybody actually wanted to try it, would be get a… Like say you wanted to do a Daily Show, get me, but absent me, I could give you a list of other free enterprise comedians that read and enjoyed Milton Friedman at some point in their life, and then just give them a staff of seven writers that are really funny, they could be libertarian, they could be conservative, they would not need to be, and just give them the remit of, “I trust you. Now, go be funny.”

29:07 Andrew Heaton: Don’t give them the remit of, “It’s your job to explain how comparative advantage is hilariously smart, like, don’t do… It’s not gonna work.” It’s gonna work for a small subset of people. For the people that already believe it, they’re gonna really enjoy it, but if you just had fun and you could sort of tell that the person was free market, it would work. But so much of those efforts are attempting to ape the Daily Show and to do so to push a political agenda, and that is not what the Daily Show did, and that’s why it will never work.

29:45 Andrew Heaton: The other part of your question, you sort of led in with there’s… I think you were indicating that there’s far more funny liberals or creative people that are liberal. I think there’s lots of reasons for that, and I’m not entirely sure. I think part of the reason might be that if you are in comedy, so much of your life has been doing things for free, hoping they might yield some positive benefit in the future, and so when you are looking at a referendum on forcing Uber to do something, you’re like, “Why don’t they just do it for free, I do free stuff all the time, quit being a dick, just be nice and do your thing,” and that’s not how people outside of comedy operate, nobody goes like, “You know what I’m gonna do? I’m gonna create a sewage company, but I’m just gonna… We’ll see if it works. Maybe it’ll be fun.” No one does that, right?

30:40 Andrew Heaton: I think that historically, a lot of the reason that there’s people that are comedians that lean left is because that used to be associated with anti‐​authoritarianism. George Carlin’s a really anti‐​authoritarian thinker, Lenny Bruce is a really anti‐​authoritarian thinker. Stand‐​up comedians in general tend to be very anti‐​authoritarian, they don’t tend to be laughing about how awesome the status quo is, they tend to be coming at it from an odd angle. That has shifted, and I find that interesting in that much of the rhetoric that you see from the left is really focused around like we’re the little guy fighting the system, and it’s okay. Granted, right now the White House is occupied by a Republican, but when I was getting into comedy, the White House, Congress, academia, Wall Street, about half of Wall Street and all of Hollywood were all progressive.

31:27 Andrew Heaton: And I was like, “I don’t… You guys won, like you’re at the cool kid table. You’re the quarter back and cheerleaders, dudes. It’s like, I’m the guy playing D and D, I’m the weirdo, I’m the little guy in this equation, not you,” but they like holding on to that. And then there might be some actual cognitive things going into that. I interviewed a really cool lady on my program coming up on a year ago, named Dannagal Goldthwaite Young, who is a really funny lady that probably could have become a comedian, but instead decided to become a communication specialist in academia, and she wrote a book on differences in conservative humor and progressive humor.

32:02 Andrew Heaton: And some of the things that she brought up is that… Actually, I’m not gonna call it progressive, I wanna make a distinction here between liberal and conservative, and I use those two terms very specifically because she only used it in regards to social issues. So for what I’m about to say, I am not referring to your fiscal positions, I’m only referring to whether you are pro gay, thrupple, smoking weed versus traditional suit and tie, that kind of thing, right. People on the conservative end of that spectrum cognitively prefer clear borders and lack of ambiguity. If you were to go to somebody who’s very socially conservative home, very good chance that all of the paintings and photographs have a frame and are very clear, like they’re not gonna have, like they’re not gonna draw on the wall, it’s nope, there’s the wall, there’s the picture, and a lot of the humor goes that same way, we’re like, oh, this is this kind of joke. It is a pun. I know how to untangle this.

33:04 Andrew Heaton: Whereas liberal thinkers tend to be more okay with ambiguity and like doing more cognitively intense equations. Again, I’m not saying that the conservative people are dumb, the raw processing power is the same, but the liberal thinkers are more apt to have kind of multi‐​layer humor and enjoy that, that takes a little bit more throttle to get through. And so there might be something to that effect as well.

33:35 Trevor Burrus: In our new religious, politically religious age, there’s been a lot of straining between friends and family about how we are able to reconcile our political differences and still be friends with each other. And I know people who have had their relationships strained with their parents and with their friends. You seem to have an approach that kind of tries to at least make communication better and to stop being so maybe dogmatic or insulting, and you kind of mentioned some of them, but how can we better communicate with our political others?

34:15 Andrew Heaton: Great question, and I think that that has been probably the most wretched aspect of the last four years, that everybody is going into citadel mode and increasingly unlikely to do that. In politics in particular, if you go back to like polling in the ‘50s, and they’d ask like, “Do you care if your kid marries a Republican,” or a Democrat, if you’re on opposite parties. And they’d be like, “No, why would I care about that?” “Do you care if your kid marries a black guy?” And like, “Oh, God, no, not a black guy.” There was really intense like racial and religious opposition to marrying outside of groups, and both of those have, I think, benefit… Have changed for the better that… That people really don’t care that much about race anymore, which is an awesome and wonderful element to American life.

35:00 Andrew Heaton: However, the political thing has really shot up to where now people are mortified if their daughter marries a Republican or a Democrat. I think that there’s a few things that you can do to combat that. The lead‐​in, I’ll say, is to recognize that we all have this tendency. Me working as a comedian, I was very surprised when I started doing stand‐​up comedy at the intensity of tribalism in everybody. When you get into comedy, you know from the onset before you go on stage, if you’ve done any reading, that everybody relates to death and sex, that these are two very primordial human impulses. Even monks at some point had an erection, even people that are completely fine with the future still fear death on some level.

35:49 Andrew Heaton: What I did not realize is that tribalism is right up there with them. In fact, tribalism oftentimes eclipses both of those things. And people get really worked up about it, and oddly enough, we don’t have really a cultural mechanism to inoculate ourselves to that. We do for sex and death, like it would be very inappropriate for me to just have sex in the street. We’ve figured out ways to kind of channel those impulses into workable solutions for society. We haven’t really done that with tribalism, what we’ve kind of done in the past is we’ve gone, well, we’ll just pick an external enemy to hate, good thing we got these Nazis, now we got Soviets and then we defeated both, and we turned around and went, well, I guess I hate you, and so we don’t have a way around it.

36:31 Andrew Heaton: So noting that, that we all have this tendency, I would say that the first thing, like my inner refrain and kind of the ethos of The Political Orphanage is good and intelligent people can disagree on matters of substance. To borrow a Thomas Sowell line, there’s a very big difference between thinking somebody is in error and thinking that they are in sin, and I endeavor to remain in that error camp of, I don’t think you have decided to be wilfully evil, I think you’re probably a good person and you have some bad ideas, and I’d like to discuss them with you. And there’s a lot of things you can do there. There’s one thing called charitable principle or the charity principle, which is a philosophical term where in philosophy circles, if somebody says something that is ambiguous, just default on whatever the smartest, kindest version of that spectrum of possibilities is.

37:30 Andrew Heaton: If somebody says something and it’s either they said something that is innocuous or they said something that’s secretly racist, just assume that they’re not secretly racist until they… If they come out and say, “I hate black people,” or whatever, that’s fine, you can call them on that, but assume that… When I’m talking to my progressive Democrat friends, I don’t think that they’re… Like when I leave the room, they turn the lights off and go, “How do we further the statist agenda to control people. It’s all about control. We all just want to get… ” Like they don’t know, they literally want to help people, I think that they have a lot of bad ideas to do it, but they have some very good intentions there, and they’re not lying to me about what’s happening.

38:12 Andrew Heaton: Same with conservatives, I disagree with conservatives on all sorts of stuff, but I think that generally they care about people and they’re not for turning lakes into liquefied radioactive waste dumps and things like that. So that is the main thing, I think, is just to go in with the premise of good and intelligent people can disagree on matters of substance. Beyond that in terms of communication and now that how Howie Hawkins is president and we’re in the future and the last four years is very much behind us, none of these matters will be of issue, but let’s say that the world had gone different and Joe Biden or Donald Trump had become president and about half the country was really pissed off and probably thought the election was stolen, then a few things that you could do in talking to people in your family or your friend group that are on either sides of this, there’s a…

39:08 Andrew Heaton: I had on Peter Boghossian and did it to talk about his book, How to Have impossible Conversations, and the two… There’s a bunch of things in that book, the two things in that book that I have found to be incredibly useful in my personal life are when I am starting to get into an intense conversation with somebody about politics, I will preface it by going, “I can tell it’s really important to you to be a good person, or I can tell it’s really important to you to help people.” I won’t lie about it, but the good news is most people are actually pretty decent, most people are actually pretty nice and want the world to be better, so I don’t have to lie. And I preface that, like, “I can tell that it’s important to you to help people,” and what I’m doing is I am, I am letting them know the conversation we are now having is not a referendum on whether you are a bad person or not, I am… I am preemptively telling you, you’ve won that, you’re a good person. Now, can we move on?

40:03 Andrew Heaton: And so now we don’t have to have this as a proxy war for whether or not I think you’re a dirt bag, it’s already established. And then the next thing that you can do is having established this, that we both wanna help people, I think minimum wage is a pretty good example. I am an outlier on minimum wage, I suspect you guys are as well, long story short, I think that you’re basically kicking the bottom rung out on the ladder and then going, “Ah, we raised the rung on the ladder and everybody at the bottom can’t get on.” When I’m arguing with people about that, it’s like, if I phrase it as… I could approach it in two ways, they say, “People don’t have a living wage, and it’s atrocious that somebody’s making $6 an hour. It’s horrible, etcetera, etcetera.”

40:49 Andrew Heaton: I could shoot facts at them and go, “Well, about… I think it’s less than 2% of the population makes minimum wage, and of that 80% moves on to a higher paying job within six months, and therefore it is an on‐​ramp to the economy.” A better approach is to go, “Well, what do we do about people that aren’t going to be worth $15 an hour? What do we do about a felon that just got out of prison that wants to like hold a sign, and maybe if that guy does well, he gets to move on and get a better job, but his labor is just not worth $15 an hour, what do we do about him?” I’m using the we because I wanna signal to that person, you and I are on the same team, we’re trying to help the situation, I’m not viewing you as an existential threat, I’m not viewing you as an antagonist, I’m viewing you as a partner to help me get a better position and help me either come out of my idiocy to wherever you are, or alternately, maybe we can come up with something good, right.

41:50 Andrew Heaton: But framing it as we really, really helps as opposed to saying you. If I’m pointing a finger, well, what do you do about this? What do you think about this? Now, I’m putting you on the spot and now you’re being… You’re gonna get in a defensive mode. So I think those are things that would help listeners a lot.

42:07 Aaron Powell: By the time this episode comes out, our listeners will know if we’ve got four years of a new president or four more years of Trump.

42:15 Trevor Burrus: Maybe not. You’re getting a little optimistic there. Maybe not.

42:21 Aaron Powell: We’ve got enough of a delay that, fingers crossed. Has Trump been good or bad for comedy, because he’s so absurd that the standard line is that you constantly, like headlines in The Washington Post have become indistinguishable from headlines in The Onion.

42:37 Andrew Heaton: Yeah. He’s been awful for comedy. Comedy has suffered. We had a dark age during the Trump years, and it’s weird in that I will occasionally see some article about the golden age of political satire, and the person will talk about how wonderful these comedians… And there are some people that are very funny, but for the most part, though, the quality of humor has declined. I’ll say as a comedian, it’s very difficult to make comedy during the Trump years, for the reason that you outline, Aaron. A big part of the comedian toolkit is exaggeration. And I’m gonna take something and I’m gonna… Now, I’m gonna put it, I’m gonna take it from a 2 to a 10. And the gap between reality and the crazy scenario that I have envisioned is so much that we shall all laugh at this absurd notion, and if I open up the newspaper and the headline reads like Donald Trump is on a battleship hitting golf balls at Democratic Senators for sport, and then the following day, he like, I will hang Rosie O’Donnell from a tree or something like that, like we’re already beginning at a 10, I have nowhere to go.

43:50 Andrew Heaton: It’s very difficult to make that funny, and as a result, we get this really sloppy, lazy humor where… I love Steve Colbert, I think he’s a really funny guy. I think he’s a comedic genius, the Colbert Report was brilliant. I know some of the writers on his team, they are very funny, very talented people, and it kills me to watch that show because it’s… Whenever I tune in, it’s just… It’s variations of like, well, the orange guy is an idiot, and I’m like, oh, Christ, I agree. Can you… Can we… Okay, yes, I can… If we all mail you a postcard saying we agree that Trump is stupid, if we all agree we’re on the same page, can we go back to doing jokes? And so much of it has been that. I think that’s more to do with the audience than it is with a lack of comedic ability on Colbert’s part. I think audiences right now are so freaked out that they don’t want actual humor, they want affirmation that they’re correct, and they just want to be just kind of coddled of, hey, you’re right, and the other guy’s wrong, just wanna remind you of that.

44:51 Andrew Heaton: And then the flip side of the coin, outside of the lazy anti‐​Trump humor, and to be very clear on this, I don’t like Donald Trump, I just also want to be funny. The flip side of that is that because Democrats this last four years have been so high strung and have just been in a constant DefCon 3 red alert mode for four years, they’re not open to any humor making fun of any Democrats, that if you make Joe Biden jokes, you are now, you are now the Vichy regime for Trump. And if I’m like… My interpretation of this election, incidentally, has been America is gonna pick between two trains, one of the trains keeps getting lost, one of the trains enjoys hitting cows for fun. Between those two options, I prefer the train that gets lost, I’m not wild about it, but I’d rather… I’d rather Biden be in office than Donald Trump.

45:46 Andrew Heaton: But if I make fun of Biden, having already established that, that I am now somehow a part of team Trump, which is just absurd. And that happens, and the other thing too, is that so much of the last four years has just become a referendum on Donald Trump that it’s difficult to even do anything else, like under… I used to do a program called Mostly Weekly on Reason, which was sort of like a Craigslist version of John Oliver, but from a free market perspective, and that was… We were hitting policy during that, and during the Obama years there was a little more latitude to do that because not everything was considered a referendum on the President, whereas so much now is a referendum on the President. And people are also kinda not super interested in stuff outside of Donald Trump.

46:33 Andrew Heaton: If Donald Trump is like writing an executive order that you’re allowed to shoot Ninjas with shotguns or something, that’s gonna dominate the headlines, and nobody really wants to hear my pithy comedy about Scotch tariffs, so, yeah, Trump has been horrible for comedy.

46:52 Trevor Burrus: If we’re looking ahead and we’ve discussed the tribalism and the religion of politics, and discussed the ways that conservatives and liberals think differently about their comedy and art and just the world in general, and we see liberals moving to… Moving to… So we have the urban‐​rural divide, so you see liberal enclaves and more rural people on the red states, do you see this getting better or is there a way that we can start talking about how to make this better no matter who wins the election? To say, hey, we can all live together, even though we like totally different television shows and we have totally different tastes in restaurants and music, at least we can all live together in a coherent country, or is it just kind of spiraling away?

47:39 Andrew Heaton: I don’t see how it could get worse, shy of civil war or secession. I don’t think that… I think that the pendulum will swing back, and right now we are in a very teamsy, yay red team, yay blue team kind of thing. I think at some point that’s gotta swing back. Sadly, it might be ’cause we go to war with Iran or China or something else, or we get attacked, and that reminds us that actually, we’re not that different. But I’ll say in the meantime, though, until that moment happens, that conflict you’re describing I think is most pronounced with people that are in media or are in politics, so the three of us, and for people that are really interested in politics like your listeners. For most Americans, it’s actually a lot less pronounced than we think.

48:29 Andrew Heaton: Morris Fiorina, a Fellow with the Hoover Institute, has a thesis that I agree with, that we’re actually not more polarized, even though it feels that way, we’re not more polarized, we’re better sorted. If you go back to the ‘60s, I’m sure you guys have talked about Barry Goldwater in 1964, right. Goldwater is a Republican at a time when there’s also Nelson Rockefeller, who is a progressive Republican and would have used that term, there’s also Richard Nixon who though a scum bag was a progressive, or at most a moderate. He wasn’t, price controls, and he started the EPA, he basically started Medicare, although they called it something different. There was a lot of latitude within both parties, if you go back just two or three decades.

49:13 Andrew Heaton: When I worked on the Hill, I worked for two Blue Dog Democrats. And so there was still a sub‐​section of Democrats that either were socially conservative, or either were fiscally conservative, but were part of the Democratic tent, and they’ve all gone into hiding, they’re… One of them’s on Tatooine, one of them’s in Dagobah. We’re hoping for a resurgence at some point with somebody’s kid. But that was the thing, and if you go back a little bit further, there used to be Rockefeller Republicans, there used to be clutches of that. And so there was a period where if you were talking to somebody and they mentioned that they were a Republican or a Democrat, you couldn’t make that many assumptions about them based on that, you didn’t know, if they said that they were a Democrat, well, are they a bourbon Democrat? Like are they like a Jim Crow Democrat, or are they a union Democrat? Or they a moderate Democrat?

50:00 Andrew Heaton: They’re a Republican. Okay, are they like a George Romney moderate Republican? Are they a libertarian Goldwater Republican or are they a progressive Rockefeller Republican? It didn’t really have that much effect, to the point that I have several relatives, that while far more conservative than I am, they’re all registered Democrat because they’re in Oklahoma, and Oklahoma was a one‐​party state for a long time. And when they registered, they didn’t view it as an existential manifestation of their spiritual values, they saw it as a little box to check so they could vote in primaries, and they never thought about it again. So there was that period there.

50:32 Andrew Heaton: It turns out that the actual polarization in the country is not significantly greater than it’s been over the last 30 years. What has happened, though, is if you’re a conservative, you’re probably a Republican, and if you’re progressive, you’re probably a Democrat. And meanwhile, about 40% of the electorate is now independent and has leanings, but is more moderate and much more centrist than we’re led to believe. Meanwhile, because the party sorting has happened, it benefits party leaders and people running for office to really pitch to the base and go hardcore ideological, so that if you’re running as a conservative Republican, you’re not running the primary based on the larger electorate or even the larger party, you’re running for the people that show up, and they’re much more conservative, and so as a result, we look at the political class and the media class, which parallels it, and we see a bunch of polarization.

51:22 Andrew Heaton: But that doesn’t go all the way down, and the nice thing that I keep reminding myself, pre‐​COVID, back when we could travel and see people, I traveled a lot in 2019, I was all over the country, I was hanging out in Portland, in Colorado, in Texas. Most people are pretty nice in person. Twitter is just a dumpster fire, like if aliens ever come down, we should immediately shut down Twitter and all YouTube comments just so they don’t destroy our civilization, just like take them to the Grand Canyon and pour them, let them see that. But like online is horrible. In person, though, I think people are actually a lot nicer than we give them credit for it, that if you… Granted, saying who you voted is gonna be the most provocative thing you can say, but barring that, if you’re at a diner talking to somebody and they’re for Medicare for All, and you’re like, yeah, I have some qualms about that. I don’t think that that would be the best way, etcetera, etcetera, they’re probably not gonna throw a glass of water in your face and then stab you with a fork and run out, whereas on Twitter, that will absolutely happen. And so the good news is it’s not as bad as we think it is, and I do think it’ll get better.


52:45 Aaron Powell: Thank you for listening. If you enjoy Free Thoughts, make sure to rate and review us in Apple Podcasts or on your favorite podcast app. Free Thoughts is produced by Landry Ayres. If you’d like to learn more about libertarianism, visit us on the web at www​.lib​er​tar​i​an​ism​.org.