Dave Barry on Humor, Writing, and Life as a Florida Man (Ep. 27)

Though most know him first as a humor columnist, Dave Barry’s career has spanned many forms of media, including books, movies, TV, and music. Driving this relentless output, says Barry, is the constant worry he’ll find himself stuck in a rut — or worse — no longer funny. And do we even need professional comedians in an age where so many funny amateurs are readily available online?

Tyler and Dave discuss all these topics and more, including the weirdness of Peter Pan, what makes Florida special, how it felt to teach Roger McQuinn a lick on the guitar, and why business writing is so terrible.

Watch the full conversation

Recorded April 21st, 2017

Read the full transcript

TYLER COWEN: Hello, I’m here today with Dave Barry, and we’re going to talk about humor, Dave’s life, and Dave’s career.

My first question about humor has to do with YouTube. A lot of the funny things you have written, rather than doing stand-up, and now there’s YouTube as a kind of competitor to written humor. How has that changed what readers are looking for? And what new constraints does that put on you?

DAVE BARRY: Well, the second part is easy: none for me. I’m too old to change. I basically do what I’ve always done.

I do think YouTube and the Internet in general have radically changed the humor industry, especially for younger audiences, which are much more oriented towards meme-y things that they see. Other people would get shorter things, shorter bits, things that require a lot of inside knowledge, which everybody seems to have now, thanks to the Internet.

And if I can extend it to not just YouTube, but Twitter and Instagram and Facebook . . . Everything happens so fast, and everything builds on everything else so quickly. Things become old almost instantaneously, or become mutated so much instantaneously, it’s really hard to keep up, which is why I don’t really try that hard, to be honest.

COWEN: If I think of the humor I consume, I’ve realized, today compared to when I was a kid, how much of it is from amateurs. There’s some one-star reviews on Amazon that are actually hilarious. Twitter can be funny; it’s very context-dependent. Maybe you know this South Korean video of Robert Kelly, the man doing an interview. He’s trying very hard not to be funny, and his two children barge into the room and are removed by his wife.

BARRY: Truly, if you were to hire professional writers to write a scene and professional actors to act, you could not possibly have outdone that particular 30-second sequence. It was just so wonderful because it was real.

COWEN: And because he’s trying not to be funny.

BARRY: [laughs] Exactly.

COWEN: But if there are billions of people out there, and say each one is really funny once in their lifetime, and some of that gets captured on YouTube, and you have aggregators or filters — as a professional comedian, you’re competing against the funniest moment of each amateur, often unintentional. So do you think it’s the case that professionals now, they become more like brands? If I watch Stephen Colbert, to me it’s funny — he’s not as funny as that moment by Kelly. He almost to me is a kind of watchman, or he reassures me. And that’s made the comedian, in a sense, deliberately not that funny. They play a different role. How do you see that?

BARRY: I don’t know, I think that the real comedians . . . Colbert, he’s basically delivering jokes written by a staff of writers and curating whatever they got from the Internet, or presenting whatever they curated from the Internet. But guys like Louis C. K. and Dave Chappelle are still creating their own humor, and it’s still really funny. And it’s them, it’s not anybody else. It doesn’t look like anybody else.

So yeah, there’s way, way more of it out there. It’s probably tougher to be really original, to sound really original, than it used to be, but there’s an awful lot of consumers as well, and there just seems to be this huge appetite for more funny.

I don’t know that it’s worse, and in some ways, it may be easier. If you are a kid who wants to get known as a comedian, you don’t really have to, anymore, go the incredibly difficult route that most of the stand-up comedians I know went, which is starting out at Catch a Rising Star or someplace much worse than that, and doing all those stand-ups in front of three drunks, and slowly getting noticed, and finally getting hired by somebody. You can just go on the Internet, make a funny video, and sometimes that will produce fantastic results for you.

COWEN: Is the half-life of a joke much shorter now?

BARRY: Yeah, for sure. As I said, I cannot keep up. Personally, I don’t even try to keep up. I see something that everybody tells me is funny, I look at it, but to try to stay on top of all the stuff that’s coming out, you can’t do it.

COWEN: But does that mean we end up in a world where, in a sense, humor is rarely intentional? And it’s the moments that weren’t expected to be captured, that’s what we laugh at. And humor is a kind of science, what will dwindle, or . . .

BARRY: Yes, that’s part of it, but as I said, there are still a lot of people who are very creative and are going to continue to be funny. They’re just going to use whatever is going on around them, and it may be a lot more Internet-oriented than it used to be. But in the end, I don’t think people’s sense of humor has changed that much. It’s sort of more the way it gets fed to us now.

COWEN: Say, 20 years from now, do you think there will be more professional comedians in this country or fewer?

BARRY: I do not represent the humor bureau, so I have no earthly idea. I do think that, in the particular field that I’m in, which is writing — the archaic form of actually writing words down — it certainly has changed. The day of the newspaper humor columnist, which is what I was, is pretty much over.

COWEN: Because the newspaper’s over.

BARRY: Newspapers are over, that there’s no more audience for it, that people have no more time for it. So longer-form humor does seem to be disappearing.

On the other hand, there’s a million good TV shows, I think, more than there ever used to be. Funny TV shows. They keep popping up — they’re on Amazon, they’re on Netflix. Some of them are really pretty funny. I can’t keep up with them all, but I’m always surprised at the quality. There seems to be more outlets, maybe, than there used to be — if for not the kind of humor that I did, but still it’s written humor, it’s scripted humor.

On anti-establishment humor, then and now

COWEN: If we think of the political content of humor — I think back, say, to the 1960s — there’s Lenny Bruce, there’s Richard Pryor. What’s funny at that time, it seems mostly to be anti-establishment, in some way, or left wing. Jon Stewart today, again Colbert. There’s some conservative or libertarian comedians. There’s P. J. O’Rourke, there’s yourself, there’s Drew Carey. But do you think that the medium of humor today has a slant politically one way or the other? And what is that slant?

BARRY: Definitely, it is a leftist slant.

COWEN: But why?

BARRY: Because that’s what the cool kids think all the other cool kids are doing. It’s kind of funny because it’s not very subversive anymore. What could be less subversive than the humor industry during the eight years of Barack Obama, where we never made fun of Barack Obama? [laughs]

COWEN: Correct. [laughs]

BARRY: He was the president of the United States. He got a Nobel Prize for doing absolutely nothing, but nobody made fun of him as they continued pounding on . . .

I’ll never forget, and here I will be unable to summon up the details, but it was one of the many White House press association dinners while Barack Obama was president. And he’s there, and Donald Trump’s there. I can’t remember who the comedian was, but he spent the whole time ripping Donald Trump, who was, at the time, some schmo in the audience. The president’s sitting right next to him, and it, to me, epitomized the way it is. We’re allowed to, in the humor biz, beat up all we want on Republicans because they’re stupid idiot Republicans, and their followers are all redneck morons.

But, at some point, that ceases to be even remotely creative. That point was reached a long, long time ago. So I think there was a steep decline in the quality of American political humor from which we haven’t really recovered, combined with the fact that a lot of what passes for humor now, on both sides, is just vicious attacks.

COWEN: Sure.

BARRY: And some of them are very clever, and some of them are very funny, but it isn’t that funny, it isn’t that creative. It’s just, “I’m going to smear . . .” How many times do you have to be told Donald Trump has weird hair? At some point, you would think this would be exhausted [laughs] as a source of humor, but it’s not.

COWEN: Do you think there’s room for a new right-wing kind of humor? Maybe not a kind of right wing that you like, but, say, now there’s alt-right — it’s at least perceived as new, it’s outrageous to many people. Is this the new direction of funny? Or is there something intrinsic about humor that it’s left wing, there’s a left-wing slant to what humor is?

BARRY: No, definitely not. Humor should be subversive, and it’s a lot more subversive to be right wing than left wing these days [laughs]. A pro-Trump humorist — I don’t know if any exist — would be a lot more subversive than any of the nine billion . . .

COWEN: Trump himself is the pro-Trump humorist.

BARRY: That’s right. [laughs]

COWEN: In a sense he’s too funny to make fun of.

BARRY: Yeah, or just too out there. He’s such a caricature by himself that it’s hard to caricature. But, OK, there’s a guy . . . Are you familiar with the blog Ace of Spades?

COWEN: Yes.

BARRY: Guy’s funny. The guy is a funny, funny writer. I don’t always agree with him, but he’s funny, he’s really good, and he’s viciously anti-left.

COWEN: Yes.

BARRY: And that’s rare, but when you see it, it’s like, “Wow! That’s different.” I admire the skill that it takes to do what he does, and I don’t see it that often.

COWEN: Malcolm Gladwell, in one of his podcasts, he criticized the Tina Fey skits of Sarah Palin. Gladwell, of course, doesn’t like Sarah Palin, and he thought that Tina Fey, even by mocking Sarah Palin — since Tina Fey was a likeable person, a likeable character — it humanized Sarah Palin for the audience, and that the satire was counterproductive. What do you think of that argument?

BARRY: It’s just overthinking it so badly.

[laughter]

BARRY: That’s not how any normal person reacted to Tina Fey’s Sarah Palin, which was brilliant. So no, I’m sorry, I don’t know Malcolm Gladwell, and I know he’s a brilliant man, but that’s way overthinking it.

COWEN: And Alec Baldwin doing Donald Trump, how funny do you think that is?

BARRY: It’s pretty funny, but again, this is a pretty easy target to be taking a swing at. There’s a big piñata up there, and everybody’s got a stick, and everybody likes to swing at the Trump piñata. I personally have gotten to the point where I don’t pay that much attention to Trump jokes anymore because they all seem to be the same joke to me: “Hey, look at what he said. He doesn’t know what he’s doing. He’s a moron.”

On crossing cultural borders with humor

COWEN: Some things cross borders fairly easily: A lot of different kinds of foods, though not all kinds of foods, some but not all kinds of music. It’s striking to me that humorous movies cross borders less, it seems from box office data, than say action movies or even what would appear to be quite culturally specific dramas. What do you think it is about the border that limits the appeal of humor?

BARRY: Probably, in part, the English language. I just speak from personal experience. What little I know of anything I’ve seen of mine that was translated, and what little I understand of the other language, it’s extremely difficult to translate humor and have it come off the same way. It’s easy to translate somebody beating the crap out of somebody else, so action movies are going to lend themselves far better.

Now, if it’s English to English, I think probably American comedies do OK in English-speaking countries. I don’t know for sure. I know English-speaking comedies from England do pretty well over here, so it seems . . .

COWEN: Canadians, on average, seem funnier to me.

BARRY: [laughs] Canada is the funniest country in the world. It just hides it much better than everyone else.

COWEN: That’s correct. But so much British humor, I literally feel I don’t understand it. There’s something about it that’s very flat to me, in a sense, that the British audience or in New Zealand, they’re guffawing. And that word guffaw — I would never use the word guffaw to apply to myself. I might giggle or snort.

BARRY: They don’t actually guffaw out loud a lot of times. They just acknowledge the humor of it in their own British way.

COWEN: That’s right.

BARRY: But yeah, you have to accept, with British humor, that no British person has ever in history ever said what he actually thought about anything. Everything that every British person ever says is meant sarcastically.

COWEN: So it’s because they’re less direct that they have such a different sense of funny.

BARRY: They are way less direct, and they refuse to ever say anything directly, and that’s the wonder of them.

COWEN: I’m the kind of person, I hardly ever find slapstick funny.

BARRY: Me too. I’m with you.

COWEN: If I look at old slapstick, it doesn’t seem funny at all. Intuitively, you would think slapstick, being only physical, would have a much longer half-life. What I find funny is very culturally specific references. Now, am I strange?

BARRY: Well, not about slapstick. When I was a little guy, I maybe thought that the Three Stooges were kind of funny but that stopped a long time ago. Some physical humor is still funny to me. Abbott and Costello were pretty physical, but they were funny without being slapstick. Just hitting each other in the nose and going, “nyuk, nyuk, nyuk” never struck me as funny at all. I have forgotten the second part of your question.

On different comedians and what’s not funny anymore

COWEN: You mentioned Abbott and Costello. If you’re willing, I’ll talk about a few comedians, or mention a few, and you can tell me what you found funny with them, didn’t find funny.

Let’s start with Abbott and Costello. Favorite of my father. I’ve watched almost all the movies. As I kid, I didn’t find them funny, but I actually started to find them funny in retrospect after having watched a bit of Seinfeld and Larry David. What’s your take on Abbott and Costello?

BARRY: Yeah, I can see the connection there. It more relies on you letting it — the humor — slowly develop and the characters themselves being the humor without coming right out and saying what’s funny about it: The one who never understands what’s going on, the one who’s always losing his patience with the other one. The first, maybe, three or four times, it’s just mildly amusing. But after a while, when you see it coming, that becomes very funny to you.

It’s very rare to find that kind of patience in humor anymore. I don’t think the audience is as generous as it used to be, allowing humor to build the way it did in an Abbott and Costello sketch.

COWEN: And is Abbott or Costello funnier to you? Abbott being the straight man.

BARRY: Yeah, I think Abbott is funnier.

COWEN: I think he’s much funnier.

Someone who just passed away, I was watching him on YouTube recently, Don Rickles.

BARRY: Don Rickles was a funny man. One of the things I liked about him, I’d say, he was a little out of control. I know that was contrived, but I think, at least early in his career, it was pretty real. You see some of the older performances, he says things sometimes on the old Tonight Shows that everybody’s just dying, and then you realize none of them really knows exactly why that was so funny. It was just that he said something that nobody would have thought to say.

COWEN: But he says some things that we, or at least I, wince at. Could there be a Don Rickles today? He’s a kind of equal-opportunity insulter. A lot of it would at least seem to be in bad taste, but since it’s applied so liberally — I mean that word in the multiple sense.

BARRY: To everybody. Well, it would work anywhere except on a college campus, where, of course, you can’t say anything at all. [laughs] But I think we have to distinguish between college campuses and comedy clubs. Comedy clubs you can still say . . . You can be racial. A lot of comedians still are very racial, and everybody says, “Yeah, it’s fine. He’s kidding. He’s not really a racist. He’s just going on the stereotypes that everybody’s aware of.”

COWEN: But I see nonwhite comedians much more deploying racial humor than white comedians.

BARRY: Generally, because they can, but even white comedians will do it as long as the understanding is, “Hey, I’m kidding. You know I’m kidding.” Which of course you can’t do on a college campus anymore because nobody’s allowed to kid.

COWEN: Do you think there’s anything people don’t find funny anymore, even in a comedy club, campuses aside?

BARRY: I will speak for my own personal experience as a dad of a daughter. If I saw a guy get up and doing underage rape jokes, it just wouldn’t . . . even if it were really brilliantly funny. The only guy who even came close was, Louis C. K. did a really edgy joke not too long ago, basically about pederasts, that came really close. And even then, everybody kind of winced when he did it, but it was daring and funny, but I myself would draw a line there.

I want to say the Holocaust, but I’ve seen people make incredibly funny Holocaust jokes. Again, it all depends on the context, and it all depends on your understanding of their sensibility, and what you’re really laughing at. You’re not really laughing at the Holocaust. You’re laughing at the anxiety or something around it. But that takes certain skill on the part of the comedian. It’s hard to say in general.

COWEN: How about Eddie Murphy? How funny is he?

BARRY: Well, he used to be really funny. His stand-up in his day was as good as it got. And what was it, Beverly Hills Cop, and a couple movies like that.

COWEN: Yes, yes. Coming to America is one of my favorites.

BARRY: I really don’t know what happened. I guess he just got too successful to need to be funny anymore, or maybe he just got tired of it, which I think happens. And, God bless him, if you get tired of it, you don’t have to keep doing it, then that’s fine, you don’t have to. You don’t have to live up to my expectations, Eddie Murphy. But he was really funny.

COWEN: Now, one of your favorites, if you could tell us what you find of value in him, and that is Robert Benchley. A lot of what he wrote was in the 20s. I was just rereading his essay on New Yorkers versus midwesterners, and who are the true Americans, and I thought it was better than things I might have read last year on the same topic. What is it about Benchley that makes a fair amount of it pretty enduring and influenced you so much?

BARRY: Well, he was radiantly intelligent. This was a very well-educated, cultured man who made a very good living as a critic, and would’ve been able to have a quite successful career as a theater critic or a literary critic.

COWEN: He was in the movies like you, his career in some ways . . .

BARRY: He was sorry that he did that, in a way. He took the money and he regretted, I think, at least . . .

COWEN: He might have regretted more if he didn’t do it.

BARRY: Maybe so, maybe so, and he did make some pretty funny shorts. But the other thing — the reason that I loved him and still love him — it was that he was that rare comic writer who was willing to be really silly. Silliness is an underrated part of humor. Most people, in the end, would rather be cool than silly, and snide and condescending than just be out there, being genuinely silly. Robert Benchley was silly. He would take extreme left turns in the middle of an essay about one thing, and it’d suddenly be an essay about something completely different, he didn’t care. As long as he thought it was funny, he went for it. And that was the thing that, when I was a kid, just drew me to him.

I was used to being presented with Mark Twain as a humorist. Now, Mark Twain is a funny guy, and he wrote some funny stuff, but you don’t laugh out loud . . . Well, you maybe do once in a great while reading Mark Twain, you smile and chuckle. Robert Benchley made me laugh out loud when I was a kid, and I thought that’s what I wanted to do.

On jokebooks

COWEN: How about jokes in books? When I was a kid — I think I was eight — I had a book of jokes, and there was one I kept on bringing around to my mother. I read it to her about five times a day. The punch line was, “I’m sick and tired of all this bickering about oatmeal.” Now today, if I say that sentence to myself in my mind, I still laugh, but I know the joke was never funny. Are just jokes listed in books . . .

BARRY: Is that a joke? Because I missed it.

COWEN: No, that’s only the punch line. The joke is not funny.

BARRY: I missed that one. OK, go ahead, I’m sorry.

COWEN: How funny are jokes listed in books? It used to be you could buy these books all the time, and now you don’t see them much. There’s Chuck Klosterman, there’s [David] Sedaris, there’s you, but . . .

BARRY: Now we have Twitter and now we have the Internet.

COWEN: But even before Twitter, it seems those books were disappearing.

BARRY: They were, they are.

COWEN: Is it because they weren’t funny?

BARRY: No, people don’t read books anymore, as far as I can tell, but if they want humor, they look on their phone. Whatever is funny now on their phone, that’s what they’re looking at. A printed page with a bunch of jokes on it would seem incredibly archaic to somebody like my daughter.

COWEN: Here’s a movie, if you don’t know it we’ll just pass, but Mike Judge’s Idiocracy.

BARRY: Yeah, I never saw the movie. I do know the principle of it. It’s way in the future, some professional wrestlers, the president of the United States . . .

COWEN: And everyone’s an idiot. The first half hour is brilliant, I think. At least watch that much of it.

When did Mad magazine stop being funny? And why did that happen when it did?

BARRY: I don’t know if it stopped being funny. I stopped reading it when I started reading National Lampoon, which struck me as more, I don’t know, a little more grown-up. Maybe I was wrong because some of the old parodies in Mad were just brilliant.

COWEN: It seems it was an influence on you, right?

BARRY: It was. I read a lot of Mad, read every issue of Mad magazine when I was 10, 11, 12, 13. And I can’t honestly say that it stopped being funny. I stopped reading it, so I don’t know.

COWEN: But maybe by the mid-’80s, it became harder for it to be daring because you have other comedians in mainstream media, well before the Internet, but being more daring. Eddie Murphy would be an example. So Mad didn’t seem so outrageous anymore. Do you think that’s it?

BARRY: It could be. And then we had a crossover into television. Saturday Night Live brought the sensibility of my generation to TV, a complete willingness to mock everything, mock commercials, the way Mad used to. Nobody on television mocked television, and suddenly there was this show that was mocking everything about television. And then the Larry Sanders Show, where it became kind of a staple of television to mock television. And Letterman, who has gone on to make a whole career out of that. So maybe we didn’t need a magazine anymore to say, “Hey, look how silly TV is.” TV was doing that for us.

On religiously driven humor

COWEN: You said in one of your essays that you can’t really pin down what makes things funny in a consistent sense; there’s something surprising about it. But you think a lot of humor stems from fear and despair. What is it you think that we fear and are despairing of so much?

BARRY: Well, the simplest thing is, we fear that we’re going to die, and that before we do, our lives are really pretty meaningless. I mean, the world is a completely unfair . . . ridiculously unfair place. Things keep happening to people that should never happen to anybody, and it seems to be pretty random how they happen.

Basically, the two reactions to that are religion — in other words, there really is a reason for all this, and it really is going to end up OK — and if you don’t buy that, then there’s humor, which is to me this weird psychological reaction human beings have developed to tolerate how scary and unfair the world is. There’s no good reason to have humor, no practical reason that I can think of. No evolutionary benefit to it other than it keeps us from going insane.

COWEN: So, in your theory, religious people are less funny because religion is their substitute, or they become more skilled at dealing with despair and so they’re more funny?

BARRY: I think they’re less funny.

COWEN: So comedians tend to be atheists.

BARRY: I think that’s true, and this is not to dismiss religious . . . My dad was a religious person, and he was a funny guy. But generally, the two things . . . One tends to mitigate the other. And to be really edgy funny, it’s probably better if you don’t believe in anything good is coming.

COWEN: Is this why so many successful comedians have been Jewish in this country?

BARRY: Well, that’s assuming that Jewish people are more likely to be atheist.

COWEN: Which I think is atheistic in regards . . .

BARRY: Which is probably a pretty good assumption. That and the fact that they’re a historically persecuted group that managed to somehow find ways to survive, using often their wits. Yeah, that’s probably part of why there are so many Jewish comedians. That and the fact that, if you’re Jewish, everybody you know is funny — trying to be funny, anyway. It’s revered in that community, that skill, the ability to make people laugh.

COWEN: Mormons historically have been a persecuted community . . .

BARRY: And they are a wacky, fun group.

COWEN: Are they?

BARRY: No, not really. I don’t know if there’s any Mormon comedians.

COWEN: Sarah Silverman.

BARRY: But they came along just for the purpose of giving — who were those guys? The South Park guys — something to make fun of, and that may be their divine purpose on Earth.

COWEN: They’re also too libertarian-oriented to have comics.

BARRY: Yeah, yeah. We libertarians love the Mormons.

COWEN: But social conservatives as comedians — that’s a lot tougher, right?

BARRY: Social conservatives — yeah, people who think there should be strict drug laws and . . .

COWEN: . . . have a prudish approach to sex. Can’t they be funny about something else?

BARRY: You’re not going to see that much, no. I don’t think so.

COWEN: But our ability to compartmentalize as human beings — just the fact that we could, say, at times, find a joke about the Holocaust funny — that suggests we’re wonderful compartmentalizers. But the people who are social conservatives, they can’t compartmentalize? What does that tell us about humor?

BARRY: Well, you have to look at the reason they are social conservatives to begin with. It’s probably, in part, because they are religious people, which goes back to my feeling: It’s not that it’s funny the world is set up the way it is. It’s because there’s a divine plan for it and rules we need to follow. This is not how a humorist thinks. The humorist thinks, “No, there’s no divine plan and these rules are stupid.” You have to be, on some level, pretty subversive to be funny.

COWEN: Here’s a question from Chuck Klosterman, from his Cocoa Puffs book. Let’s see what your answer is. “Every person you have ever slept with is invited to a banquet where you are the guest of honor. No one will be in attendance except you, the collection of your former lovers, and the catering service. After the meal, you’re asked to give a 15-minute speech to the assembly. What do you talk about?”

BARRY: I would try to seduce the catering service, they being the only people there I haven’t already slept with. Oh man, that would be . . .

COWEN: I would complain about the catering service.

[laughter]

BARRY: First of all, it might be, in my case, not that huge a group, to be honest. I could just address them individually. It wouldn’t take that long.

COWEN: But it would include your wife.

BARRY: Yes, yes, I have slept with my wife.

COWEN: Are there common targets of humor you think are unfairly maligned, other than the common tendency to attack, say, Republicans or the Right, but at the social level?

BARRY: Well, not so much anymore. There was a time when half the jokes you heard, and this was in my lifetime, were Polish jokes, whatever. And as we think back, it was kind of stupid. Polish people are not less intelligent.

COWEN: Chopin, right? Let’s joke about Chopin.

BARRY: And yet that was a staple of humor, and some of those were pretty funny jokes. You don’t hear them anymore. But now, it’s more likely to be a political target, and whichever side it is, I’m inclined to view that kind of humor as lazier. It’s more like, “I know you’re on my team, so if I mock that person, we’ll both get a good laugh, and it also will prove we’re smarter than them.”

That’s kind of the format, the template, for a lot of humor now. And for the most part, it’s not really based on anything real. It’s kind of silly to pretend that all Republicans are stupider than all Democrats, in my opinion, or the other way around. Either way, it’s kind of a dumb template to start with, and yet that is the template now for both sides.

COWEN: One of my readers sent in a question: “Would love to hear him talk about sentence structure and its relationship to the effectiveness of written humor.” Do you have any comments on that?

BARRY: I do, I do. This is my life, writing sentences that are intended to make people laugh. And you start with the idea of the joke, but then to execute it so that it actually works — it’s very similar to what a stand-up comedian does, but he does it with timing and emphasis. In written humor, you do with it spacing and punctuation and a few other tricks. But the key — and this is the most obvious example of why sentence structure is important, and yet it is violated all the time in humor writing by amateurs — is that the funny part has to come last. And then, when it comes, it has to end there and go on to something new.

Very often, the funniest part of the sentence, if it’s poorly done, will be in the middle, and then there’ll be words after. If you watch a stand-up comedian, he’ll never deliver a joke where there’s more words after the funny part. But in written humor, that’s done a lot by people who don’t know what they’re doing. So yes, sentence structure is really important.

On why business writing is so terrible

COWEN: And how formally do you think about grammar when you do this?

BARRY: A lot. For a long time — well, it seemed like a long time — seven or eight years, I taught effective writing seminars to business people. I was young, and I looked even younger. But I had to get up in front of engineers, chemists, lawyers, sometimes accountants, people who were accomplished in their fields but were not necessarily good at writing, and I was supposed to talk to them about how to write reports and letters and memos. And they challenged me because I looked like I was 10 years old, and they expected to be bored also.

I became a grammar fanatic in self-defense because I got challenged so often: Why do I say it’s OK to end a sentence with a preposition when they were told that you can’t do that? Why did I say it was OK to start a sentence with “and” or “but” when they were told you can’t? They had all these rules that they were told that aren’t rules of grammar and never were. I could — I don’t think I can anymore — I could diagram sentences, I could cite usage experts.

So I became very interested in grammar. I was always a pretty good writer, but I was a much more aware writer when I came out of that experience. Now, I use grammar more to mess it up for humorous effect. I don’t try to teach anybody grammar, but I did find the grounding I got was helpful.

COWEN: You once wrote that, after eight years of trying to teach business writing, you became convinced it would never get any better. But this is now later, we’re in different time, there’s the Internet, which actually gets many people writing much more, not always for the better. But do you think, fast-forwarding to 2017, has business writing in any way improved?

BARRY: I’m not as on top of it as I was when I was reading hundreds of letters and memos every week, but my guess is no. There are certain fundamental things that businesspeople have trouble with.

COWEN: What’s the main thing they get wrong from the business mentality?

BARRY: OK, the most consistent mistake . . . not mistake, but inefficiency of business writing — and it was very consistent — is the absolute refusal on the part of the writer to tell you right away what message he or she is trying to deliver. I used to say to them, “The most important thing you have to say should be in the first sentence.” And “Oh, no, you can’t. I’m an engineer. We did a 10-year study, this is way too complicated.”

And inevitably, they were wrong. Inevitably, if they really thought about it, they were able to, in one sentence, summarize why it was really important. But they refused to do that because the way they found out was by spending 10 years of study and all this data and everything, and that’s the way they wanted everyone to look at what they did. They wanted their supervisors to go plowing through all they had done to come to this brilliant conclusion that they had come to.

COWEN: Through their history, through their thought patterns.

BARRY: Drag everybody through it. And it was the one thing the newspaper people were taught to do that made more sense. You don’t have your reader’s attention very long, so get to the point. I found it was very difficult to get even really smart businesspeople to get to the point. Sometimes it was because they really couldn’t tell you what the point was.

What I wanted to say, but rarely felt comfortable saying, was, “If you don’t know what the point is, then you can’t really write this report.” But it was always too complicated for a layperson like me to understand. That was the way they did it. I was being hired by their bosses to tell them, “No, we want you to write clearly, and we want you to get to the point.”

And it was the one thing the newspaper people were taught to do that made more sense. You don’t have your reader’s attention very long, so get to the point. I found it was very difficult to get even really smart businesspeople to get to the point. Sometimes it was because they really couldn’t tell you what the point was.

COWEN: And why were they, at this meta level, resistant to your message?

BARRY: Because nobody else was doing it. When I would start the class, I’d have 32 people in the class typically, and when they would turn in all their samples of writing, every one of them wrote the same way. They all wrote business-ese writing. This is my parody of it, but it was, “Enclosed please find the enclosed enclosure.” That kind of formal, nonsensical, meaningless flow of words. Somewhere in there would be something important, something significant, or maybe not.

COWEN: And were the women worse or the men worse?

BARRY: Both sides were equally bad.

COWEN: In the same ways?

BARRY: I did not notice a difference based on gender. I just found very few people are naturally clear, concise writers. That’s not a common trait. But it was more of a thinking issue than it was a writing issue. It was just this inability to see the purpose of the document as anything other than a diary to make you see what I did as opposed to convey important information to you.

On humor as a public good

COWEN: Humor is one area where the enforcement of intellectual property law tends to be weaker, maybe even nonexistent. So there are always issues or problems with comedians stealing jokes from other people, whether stand-up routines or in writing.

Do you think it works having an area such as humor where basically IP law isn’t applied, and there are various conventions, and you hope that other people punish those who break the conventions, but you can’t rely on that. Or is humor this public good that is actually underproduced because we don’t have property rights in jokes?

BARRY: Well, it’s not underproduced [laughs], there’s plenty of it out there. It’s kind of self-policing, and people do steal. I have had, over the years, ridiculous experiences, especially when my column was syndicated. Somebody would send me a copy of this local shopper, and the local orthodontist wrote a weekly column. And one week I would look at it, and it would be my entire column word for word with my name changed to his name. And I’d write or call these people when I was younger and more naive and had more energy, and I’d say, “You stole my column. You just took it.” And they’d go — they were never apologetic — it was like, “Oh, I just thought it was so great.” I’d say, “But you stole it. You put your name on it.”

They didn’t get that that was wrong, but I think it’s harder and harder to get away with that. If you are a successful comedian, people are going to catch you if you’re stealing somebody else’s jokes. There’s just too many people out there consuming it, seeing it in too many different forms.

COWEN: Who’s a comedian who’s not so well known, who you think is fantastic and ought to be better known? Written, stand-up, television, whatever.

BARRY: I don’t know. The ones I would name are known.

COWEN: But even someone like Robert Benchley, while he’s on one hand famous — his Wikipedia page is quite long — he’s not actually known. Most people haven’t heard of him.

BARRY: Nobody knows who Robert Benchley is anymore, and this is one of the things I’ve been using for years as an example of why I don’t expect to be famous for anything in 20 years, except for Talk Like a Pirate Day, which wasn’t even my idea. People who do humor, with the rarest of exceptions, do not last in the culture the way people who write Tender Is the Night hang around for much longer. We talk about the Marx Brothers but who goes to see Marx Brothers movies anymore? We know who they are, but people still go to see Shakespeare performed, not to compare.

COWEN: When there were repertory theaters, I went to see Marx Brothers movies and Duck Soup, at least, I think held up pretty well.

BARRY: Yeah, because you’re old like me.

COWEN: Yes.

BARRY: And they still showed the movies when we were younger. But you don’t go see any more of Marx Brothers . . . Yeah, Duck Soup holds up great.

COWEN: That’s the best one, I think.

BARRY: Yes, but even then, there’s stretches in Duck Soup [laughs] where it just . . . Oh man, he’s really kind of dumb, but it’s so dumb, it’s kind of funny.

On being a Florida man

COWEN: Your latest book is about Florida. So I thought I would go to news.google.com and just enter “Miami.” This is one of the first articles that came back: “Miami Beach police say Sigman Hernandez confessed Wednesday to ‘slapping and possibly choking’ his tiny Yorkshire Terrier and leaving her in a Publix parking garage. The reason, he told police: The dog vomited in his car.” I then went to your blog and there was a story there of “Zachary Kelly, 30, became upset with Phoebe, a four month old puppy who was acting up. They said he held the animal down and bit her on the ears [laughter] and he was ‘just trying to teach the dog a lesson.’”

BARRY: Teach the dog a lesson.

COWEN: Now, what is wrong with the dogs in your state?

BARRY: [laughs] The dogs are fine, the people are not. Yeah, Florida, the guy who bit the dog. After hearing the expression “man bites dog” nine trillion times, I don’t think I’ve ever actually seen an example where a man did bite a dog.

[laughter]

BARRY: But if he did, naturally it had to happen in Florida. And that dog will not do that again, whatever it was.

COWEN: Why has Florida evolved to become weirder, say, than neighboring states?

BARRY: Well, many reasons — first of all, it’s warmer than . . .

COWEN: Is it much warmer than Alabama?

BARRY: Yes, quite a bit warmer than Alabama.

COWEN: OK, warmer than Alabama.

BARRY: Come to Alabama in January, and then you’ll want to come to Miami. It’s warmer, it’s much more known as a vacation destination. It’s got beaches everywhere. People come there not for serious reasons coming there.

COWEN: Doesn’t that make them calm, though, rather than weird?

BARRY: No.

COWEN: Is it the giant insects that make them weird?

BARRY: It makes a lot of them drunk, is what it makes them. We have ready access to alcohol and drugs of every kind in Florida. We have a lot of different communities that have absolutely nothing to do with each other, living in close proximity. Miami-Raleigh is a good example, but the whole state — it’s like 10 different weird little communities. There is no Florida; there’s no sense of state pride. People don’t go, “I’m a proud Floridian.” They just don’t. It’s like nobody owns the state, and there are people just constantly showing up in the state for various reasons. I would say we’re like the Ellis Island for stupid, weird people. If you want to pleasure yourself into a stuffed animal in a Walmart, you’re going to go to Florida to do that. You want to get naked by the side of the road for no apparent reason, Florida’s the place you would like, if nothing else, because it’s warmer there.

COWEN: And the law enforcement is different. But they caught this man biting the dog. They caught the man who kicked the dog through the parking garage, so it’s tough on law enforcement?

BARRY: Oh, we eventually do arrest people usually, but sometimes it’s the police officers doing these things.

[laughter]

BARRY: No, I don’t know . . . It’s a state where every day is 1,000 more people than there were the day before. So there’s a lot of people that just showed up ready, looking for something in the heat and the humidity, with the bugs and the lizards and the booze, and it’s just this toxic stew of weird, is what it is.

COWEN: I was thinking, what to me is special about Florida? And one thing that struck me, asking some others as well, is how many wonderful or at least interesting movies are set there. So a simple list would be Body Heat, Spring Breakers . . .

BARRY: Body Heat was an incredibly good movie.

COWEN: Of course it is, as is Spring Breakers, Key Largo, Contact, Deuce Bigalow, Ace Ventura, a Canadian comic, by the way. Some Like It Hot, all kinds of space movies, Ulee’s Gold, an old movie with Peter Fonda, parts of Midnight Cowboy. All kinds of gangster movies have scenes set in Florida. So why is Florida such a wonderful place to set your movie?

BARRY: Probably because, I’m guessing, it has something to do with unions [laughs] more than anything else? Yes, it’s warm, so you don’t have to worry quite as much about the weather down there. And again, it has an image to it. People don’t think of Florida the way they think of Alabama, even though Alabama’s right next door, but they think of Florida as more exotic. And they’re right, it is more exotic. It’s more exotic than any other state, as far as I can tell.

COWEN: And you live near Miami. Let me ask you a question about that place, which I’ve been to many times. Am I wrong in thinking that maybe 15 years ago Miami was more culturally central than it is today? Spanish as a rising language was arguably more important. There was a sense Miami might become or be cemented as a capital of Latin America.

It seems now even Latin America, in some ways, has just turned its back a bit on Miami, not in a hostile way, but they’ve developed their own urban centers more, media empires outside of Miami more. And it seems to me a slightly forgotten city along with Los Angeles. Art Deco people aren’t as interested in it anymore, maybe for the better of Miami.

BARRY: I don’t want to get all chauvinistic, but I dispute all of those. All of those. Miami is growing like crazy.

COWEN: Oh, it’s grown, but is it as central to the American consciousness as a rising urban center, as it was 10, 15 years ago?

BARRY: I think, maybe in a sense that everybody’s more used to now, that they know Miami is really the capital of Latin America, but I don’t think it any more than New York has become passé. It’s just cemented, that’s what it is. Miami is the center of Latin America, but it’s exploding right now. I don’t have any statistics to back up this feeling I have, but I haven’t noticed that Miami’s turned into some kind of backwater.

COWEN: We run our government out of Florida now, right? At least the executive branch.

BARRY: Mar-a-Lago. That’s up the coast a little bit with the rich people, but yeah.

COWEN: But it’s not very far.

BARRY: No, it isn’t in linear distance. It’s a million, trillion miles away in culture. Palm Beach and Miami are separated by Boca, which is Long Island, basically.

When you get across the Dade-Broward line, you are in Latin America. Eighty percent of the city, I think, speaks Spanish as its first language, and a lot of people don’t speak any English at all. You can function comfortably in Miami your entire life, and never speak a word of English, read a word of English. You just don’t need it. Whereas if you are in business in Miami, if you don’t speak Spanish, you’re in big trouble. You’re going to need it, so it’s still a very, very, very Latin city.

But when you get to Fort Lauderdale, and then Boca, you’re in New York. Then you get a little farther, and you’re in Palm Beach; you’re just in Rich Person Land.

COWEN: I sometimes feel that parts of Puerto Rico are more American than parts of Miami, actually.

BARRY: Oh, definitely. Miami is not American, it’s Latin American. It is Nicaraguans and Colombians and Venezuelans and Dominicans. All of these people like the United States, but a lot of them have not really assimilated to the United States particularly well yet.

The one that everybody talks about is Cubans. My wife is Cuban, my in-laws are Cuban. They are Americans. They’ve lost their country, and they’re OK with that. They’re still very Latin, but they’re Americans. But there are large sections of Miami where people are still living essentially in Colombia, or might as well be.

COWEN: And is there, to you, a central author or cultural figure who represents Florida in some way?

BARRY: No, absolutely not. The closest you would get would be Carl Hiaasen.

COWEN: Carl Hiaasen, yes. That’s who comes to mind.

BARRY: [laughs] And he kind of represents the “I’m really sick of what’s happened to my state” side of it. Carl does not embrace the changes of Florida. Carl will be happy if it went back to just being mostly snakes and lizards.

COWEN: You have Zora Neale Hurston, and also Gram Parsons was from Florida. Even though people think of him as somehow southwestern, his country sensibility is very much eastern, actually.

You said in one of your writings, you’ve lived in the suburbs of New York City, Philadelphia, and now Miami, maybe other stops in between. Do you think the suburbs are underrated?

BARRY: Yeah, at least where I live, in Coral Gables, which is a city but it’s really a suburb of Miami. It’s a pretty great place to live. What it has in common with the other places that I’ve lived is, it has access to a major metropolitan area with the excitement and the diversity that that implies, but you can be physically more comfortable, and I like that. I think there’s nothing wrong with that. I think there’s a reason people want to have a yard, and a driveway, and I think every American should have a right to a yard and a driveway.

On the Dave Barry production function

COWEN: The one thing that really struck me, going through your life history, is the depth and breadth and comprehensiveness of what you’ve done, in so many different media. You’ve written children’s books, you’ve been involved with television. You’ve obviously been on the Internet. You wrote a weekly column for many years. Business writing. Worked with Walt Disney. There’s a rock group called the Rock Bottom Remainders that you were in for a while.

My sense is there’s something quite special about your work habits that is maybe the most remarkable feature about you. So, if someone were trying to build a career in soxme way, and they said, “Well, I want to learn from the work habits or the career management of Dave Barry,” what has been going on behind the scenes that accounts for your extraordinary productivity, defined along a number of different dimensions?

BARRY: Well, first of all, thank you! That’s the most complimentary thing anyone’s ever said about my work.

COWEN: It’s really striking.

BARRY: Part of it is insecurity, so I want to keep producing always.

COWEN: So fear and despair?

BARRY: Fear and despair.

COWEN: Which makes you funny.

BARRY: And the constant worry that you no longer can do it, and that you’re not funny any more. As soon as you start to be pretty confident that anything you write is great, then you’re going to suck in any creative field, I think. But then also, a certain impatience or fear of getting into too much of a rut, so wanting to try new things that you feel are in your wheelhouse. If I had said that I wanted to become a playwright, I think I would’ve been stretching too far. I don’t know anything about being a playwright. I wasn’t trained, I haven’t studied, whatever.

As soon as you start to be pretty confident that anything you write is great, then you’re going to suck in any creative field, I think.

But I did feel that I could go from writing funny essays to maybe trying to write a funny novel — if I looked at the funny novel as a series of funny scenes with some kind of plot, which is a crude way of looking at it. But at least it was connected in a way that I thought, maybe, could make it work.

It’s a combination of insecurity, needing to keep producing, and fear of boredom, wanting to do something new that you still felt you could do competently, or at least not embarrass yourself.

COWEN: What was it like playing music with Roger McGuinn?

[laughter]

BARRY: There’s when I’m embarrassing myself. This has been the most fun thing I have done as a grown-up. I’m writing a book now about things I’ve learned from my dog, essentially, and one of the lessons I’ve learned from my dog is that you should not stop trying to have fun, even when you get old. And the most fun thing I have done as a grown-up is be part of this rock band called the Rock Bottom Remainders, which is not a good rock band, and I’m not a good musician.

COWEN: What do you play?

BARRY: I play guitar. I did it in college, and I’m good enough that if you didn’t know anything, you might think I could play guitar. But if you know anything, you would know immediately that I can’t. That I just can fake it reasonably well.

But anyway, I got to play with, not just Roger McGuinn, but Bruce Springsteen and Warren Zevon. Roger plays with us regularly. He still does, although it’s been a couple of years, I’ve got to admit. And that has been the most fun, single fun thing because it is unlike what I was just talking about, where you want to be in your wheelhouse, you want to be where you can be competent. It’s an area where I know I’m not competent. I don’t belong, and yet I get to be on the stage with this guy who’s really, really great.

COWEN: And what’s Roger McGuinn like?

BARRY: He’s the nicest man, and that’s been the thing, the consistent thing with these musicians who have played with . . . Well, I guess you have to be nice to be a great musician who’s willing to play with a bunch of incompetent authors.

But Roger . . . I’ll never forget the first time we played, and I can’t even remember . . . Oh, yeah, we were playing somewhere, and Roger wanted to stay on stage with us. We did a series of Byrds songs with Roger, and I said, “The last song we’re going to do after that is ‘La Bamba,’” the Richie Valens song. And he goes, “Oh, OK, I’ll do that.” And he goes, “What key do you do it in?” I go, “G.” And he goes, “Well, how does that lick go?” And I happen to know it. “Dah, dah, dah, dah, nah, nah, nah, nah.” I can play that lick, and I remember just, “It goes like this . . .” And Roger’s looking at it, and I’m thinking, “Roger f — ing McGuinn is looking at my left hand to see how to play a lick on the guitar.”

To me, that’s better than winning a Pulitzer Prize. It’s really much more fun.

On the weirdness of Peter Pan

COWEN: You have a whole series of books. Peter and the Starcatcher is based on Peter Pan. Many have been bestsellers. It’s believed that more than half of the audience for these books is adults, although superficially, they might seem to be children’s books; they’re that, too. The original novel, Peter Pan, by J. M. Barrie, how do you understand that book? It’s a deeply weird book. What’s your sense of that book, and then how you and your coauthor, Ridley Pearson, modified Peter Pan?

BARRY: We were really naive. Neither one of us had really spent much time on J. M. Barrie. Both of us had been raised in the United States, and our view of the Peter Pan story was the Disney cartoon, the famous Disney cartoon, and Mary Martin on Broadway hanging on wires, you know, this 43-year-old lady swinging around stage.

That was our view of the Peter Pan story. And all we were thinking about was that, the American version of the Peter Pan story. The myth with just a few simple elements — He can fly. Tinkerbell, Captain Hook, the crocodile — the simple elements. How could we put those together in a backstory that would be entertaining for kids? Little did we know we were sticking a stick into a hornet’s nest of British people who take their J. M. Barrie very, very seriously, don’t like Americans . . .

COWEN: It’s like trying to revise Star Wars.

BARRY: Right. They don’t like Americans anyway. So we got a certain amount of grief from the purists, and we had to, from the start, say, “We don’t say we own this story. We’re not saying we’re experts on this. Here’s what we’re doing. We’re a couple of American guys taking the American view.” That was our idea, and it worked out really well for us.

COWEN: One of J. M. Barrie’s siblings claimed that J. M. had never had sex. Now, we know from one of your earlier answers, that’s not the case with you. Is this a dark vision of Peter Pan?

BARRY: Well, I went back and read it, and yeah, it’s more . . . I would say more weird than anything else. Just kind of a strange story, the way it’s told. And I honestly can’t say I was a huge fan of it.

COWEN: You know, Mary Gaitskill wrote recently that it’s about how young men are not interesting and women of all sorts are completely replaceable. And you go through life with these relationships, and they’re all transitory and meaningless, and somehow from that comes a book that people are dearly attached to. And that to me is strange.

BARRY: It is strange, but I always felt that what they were attached to . . . because if you listen to people, they don’t quote long passages from Peter Pan. In the end, when you ask almost anybody, certainly any American, “What’s Peter Pan about?” “It’s a little boy who never grows old and can fly.” All of which is true, but you don’t get . . .

COWEN: But that’s a little sick in a way, right? A little boy who never grows old and who can fly? Would you want that life?

BARRY: When I was eight, yeah. [laughs] That’s the appeal.

COWEN: And in retrospect?

BARRY: No, I could not . . .

COWEN: It’s a kind of punishment, one of Dante’s circles of hell.

BARRY: And not to get all heavy on it, but in our books, we do try to deal with the fact that Peter has to accept that his friends are all going to grow old and leave him. As J. M. Barrie does. That is, in a way, the sad part of it. Although, mostly, it’s, “Isn’t it cool that he can fly.”

COWEN: But your Peter Pan is more of a bildungsroman where Peter develops in a healthy direction.

BARRY: Yeah.

COWEN: It’s more for Americans.

BARRY: And there’s a girl who’s really great and strong and nice and brave.

COWEN: And does she really love him?

BARRY: She does. They do, but they can’t ever be really in love because he keeps the same age and she keeps getting older.

COWEN: And are you ever tempted to be funny in those books?

BARRY: Yeah, there are a couple of scenes where I go for humor. But one of the things that I like about writing novels is that you don’t have that burden on you. When I write a humor book, my feeling is, every sentence is supposed to be funny or leading to it, the next sentence, which’ll be funny. And with a novel, you’re telling a story, which to me is a much more relaxed process, less frantic when I’m writing it. “What would he say then?” And, “What would he say then?” And, “What would they do then?” That would keep you engaged, but it doesn’t have to make you laugh, which is a lot of pressure.

What Barry’s doing next

COWEN: And to close, could you give us any hint as to what you’re planning on doing next?

BARRY: Continued immaturity followed by death is my plan. Now, I’m writing a book. As I said, it’s about dogs. It’s about my dog, whose name is Lucy. And it’ll be called, I think, Lessons from Lucy. I’m going to turn 70 this year, and Lucy’s going to turn 70. She’s 10, so in dog years, 70. And I was thinking about it, when I was thinking about a dog book, and I was thinking, “She’s still really happy.” She’s unchanged in that sense — in the happiness sense. She’s changed in her appearance and what she can do and everything, but she’s still pretty happy all the time. And I’m thinking, “What does she do that I don’t do?” Because I’m pretty clear, I’m not as happy as I was when I was 19. I was a lot happier.

COWEN: Oh, I’m happier than I was at 19.

BARRY: Were you really?

COWEN: Yeah. I think for most men, happiness between 30 and 60 are the peak years.

BARRY: Well, I’m way past that. I’m on the downhill slope. So I’m looking to my dog for help.

COWEN: Yeah.

BARRY: And if she doesn’t give it, I’m going to bite her.

COWEN: Dave Barry, It’s been a pleasure chatting. Thank you very much.

BARRY: Same here. Thank you.