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.
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?
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.
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.
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.
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.
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.”