And Here's the Kicker: Conversations with 21 Top Humor Writers on Their Craft

by Mike Sacks

  I took vacations and trips, but I could still write my column — it wasn't that difficult. But that's not saying I was like Mike Royko. I still don't know how some columnists did it, Royko being Exhibit A.

  How many columns did Royko write in a week, first for the Chicago Daily News and then later for the Chicago Sun-Times and the Tribune?

  He wrote every day and, you know, if he didn't publish a column, the newspaper sales would drop by $100,000. At least this is the legend. He just felt this immense pressure to be in the paper every day. I don't know what that must be like. I never felt that type of pressure.

  Was there ever any frustration that you couldn't spend more time honing and re-writing an article?

  No, I had a lot of time. And again, I had the advantage of writing only one column a week. I was always sure when I sent in the column that it was the best I could have done. Now, there were times when having done all that work I would think that that wasn't the greatest topic for me. There were also times when I would look at a column after it was published and think, Man, I could have done that better. But I never had the feeling that I was just getting it in because there was no additional time to work on it. With that said, every now and then, when I would be at a political convention or at a sporting event working on deadline, I might have felt that more time would have been nice.

  You started off as a reporter. Does your ability to write quickly come from that background — when you would consistently have to crank out articles before deadline?

  I definitely think starting out as a journalist is good training for a columnist. You begin to understand the cycle of the paper and the deadlines, and you don't think in terms of writing for the ages and literature and future generations — you just think in terms of getting it in the paper.

  As you say, you had a week to write a column. But, for a humorist, a week isn't a long time. Many humorists are famous for re-writing a piece endlessly.

  Basically, I had a two-or-three-day cycle where all I was doing was dealing with my column, and that's a real luxury to me. After that it would be diminishing returns, or no returns. When you write humor, it's not funny to you. It's not even really that funny when you first think of the idea. There may be a glimmer of humor because it still seems vaguely original, but after a couple of days it's not funny at all. You're just trusting that it was, at some point, funny, and that your honing and tweaking is really improving it. I would eventually reach a point where I would just think, This feels old, even though nobody's seen it but me.

  You once said you were happy that readers didn't know how your humor column was written. That a reader would have been disappointed by learning how the trick is pulled off — you compared it to being a magician.

  I've often said that about humor, both spoken and written. It's a lot like a magic trick, in that there's a very mechanical way in which it's done. There are a lot of obvious and basic structural things you do with a sentence and with a joke and how you set it up on the page. And the trick is to do it in such a way that it doesn't look like there was any effort involved — that it's somehow magic.

  When a good stand-up comic is performing, he gives you the illusion that he's thinking of these things as he's speaking — every now and then this may be true, but generally it's not. Generally, he has practiced every single joke, every single pause, every inflection, every facial expression, and found the ones that work the best. And when he does this quickly, it's hilarious. To him, it's executing something. And I think that's what writing humor is sort of like. There's a certain amount of inspiration, but there's also a fair amount of work and repetition and practice and mechanics that are involved in making it look like it's just happening magically, right then and there.

  Where did your reporting career begin?

  I worked for a little newspaper called the Daily Local News in West Chester, Pennsylvania, a suburb of Philadelphia. It was boring. I spent a lot of time reporting on sewage. When I was in college, it was nowhere on my radar screen, sewage. I never had any idea as to what happened after you flushed the toilet. But when I got to the paper, as far as I could tell, sewage turned out to be the main thing the local governments dealt with. I spent many, many hours in meetings where people would talk about sewer lines. I never really understood what they were talking about, but I would have to write about it anyway. I'd also write about school-board meetings, and I wrote obituaries. For me, the occasional excitement would be a fire or a shooting — something that felt newspapery.

  Young people who want to become columnists are always talking about how they don't want to be reporters; they just want to be columnists. I'm always telling them they should be a reporter first. Because if you learn to do that, to collect information and write an accurate news story, you'll be much better at making fun of it.

  How did your syndicated humor column begin?

  I was writing for the Daily Local News for a few years, and then, at the very end of the seventies, the very beginning of the eighties, I started getting a humor column into that and other papers. Sometimes I would even get the column into some of the bigger newspapers, such as the Philadelphia Daily News or the Inquirer.

  Then a teaching opportunity became available. It was totally unplanned and unrelated to humor writing, but it was a very fortuitous change for me. It yanked me out of journalism altogether, and it put me into a world where I was traveling a lot and talking to people who worked at big corporations — something I knew nothing about. I was an English major from a small liberal-arts college, Haver-ford, where we didn't even know what business was. After I graduated, I went into journalism, where I still didn't know what business was about.

  And then, suddenly, I was in this new world, dealing with people who participated in the economy and who made paint or who made cars, and actually produced things. It was my job to teach these people how to write more clearly. You know, letters and memos and reports. I learned a lot. It was just sort of looking at the world in a different manner. And I had more time to write, because I was in planes and hotels and on the road a lot.

  That's really when I concentrated on writing my humor column. I could write about whatever I wanted. It didn't matter to me if it was unlike any other newspaper column, because it was only running in the Daily Local News, and it wasn't my full-time job. I thought I was going to be teaching writing for the rest of my life, so, in a way, it gave me this chance to just sort of explore this voice; to become the type of humor writer that I wanted to be, and not have to worry about whether or not some editor sitting at his desk was pleased by it. It didn't matter. I could do whatever I wanted, which was the same thing I had done back in high school and college, writing silly little pieces, similar to Robert Benchley's, who was my idol.

  That's quite a leap: from teaching businessmen how to write to having your own nationally syndicated humor column.

  It was a slow process. Basically, what really got me going was an essay for The Philadelphia Inquirer in 1981. I wrote this long piece about natural childbirth that came to the following conclusion: it hurts. Which was a major insight for me, because the one thing they never mention when you go through all of the childbirth training is that it's quite painful for the woman. I mean, it didn't hurt me, as a man, but it was quite painful to the woman.

  So I wrote this essay, and the Inquirer played it big, and it was just the right thing at the right time. Every baby-boomer was having a baby or two at that point, and every one of them was going to natural-childbirth classes, as far as I could tell. And a lot of them were newspaper people. And that particular column got reprinted, I would say, in two dozen big papers. And it went over really well. A lot of these editors suddenly started calling me and asking, “What else have you written?” I had a year's worth of samples, and it wasn't long before I was regularly being published in a bunch of papers. Not too long after that, in 1983, The Miami Herald hired me.

  What was Miami like then?

  It was very different. In some ways it's stil
l bad, but back then it was much, much more scary, and very unsure of itself. Today, Miami has sort of established itself, I think, as the pre-eminent party city of the United States. This is the natural place for the Super Bowl, because there's nothing but clubs and restaurants here. It's a little bit like Las Vegas in that sense, where people just think of it as a fun place to go. But in the early eighties, a lot of people in Miami were leaving and moving out, and there was quite a lot of fear, especially among the Anglos. There are still people who feel this way, but I think they're mistaken.

  So, in 1983, I didn't want to move here. I just didn't. I lived on a shady, wooded road in Pennsylvania. To me, Miami was the weirdest place I'd ever seen in the U.S., but The Miami Herald was so determined to have me write for them that they hired me even though I stayed in Pennsylvania — for the next three years. I was the Miami Herald humor columnist living in Pennsylvania. Finally, in 1986, I moved here, and I've been here ever since.

  Do you think the location has contributed to your humor? That if you had stayed in Pennsylvania, your style or sensibility would have been different?

  Not really in the style that I write, no, but certainly the things I wrote about changed. Miami was, and still is, a gold mine for humor. Not long after I arrived, in the fall of 1987, the Pope visited and almost got killed by lightning. That's what I remember most about that time: the Pope was at a gigantic outdoor rally, and just when everything was set up, this huge Miami thunderstorm rolled in and they had to rush the Pope out of there before he was obliterated into a charred cinder.

  I also remember being at a bar on Biscayne Boulevard when the Pope rode past in his Popemobile, and there were maybe eight people on the street. Everyone else had stayed home, because the Herald had managed to successfully terrify everybody into not leaving the house and just watching the Pope on television. We heard things like: If you plan to see the Pope, leave now! You should have left yesterday! You should have the following items: flak jacket, raincoat, insulin!

  You don't get that sort of thing in Pennsylvania.

  When did you win the Pulitzer?

  In 1988, for articles I had written in 1987.

  Did this come as a surprise?

  A huge surprise.

  Was there any worry on your part that winning the Pulitzer would affect your humor? That you were now part of the club, and no longer an outsider?

  I worried about that a lot. I didn't realize at the time how big a deal it was to win a Pulitzer. I didn't realize that you get bombarded with telegrams, that you get asked to be on all these TV shows, and that everybody you've ever known gets in touch with you. I wasn't ready for that. And I had this feeling like, you know, jeez, does this mean that I'm still allowed to write stupid columns? Because my column won in the distinguished commentary category. No one had ever called my writing “distinguished.” So I really wrestled with my first column after winning.

  What was that first post-Pulitzer column about?

  Even before I won, I had been planning to write about my dog throwing up.

  I had a little dog named Zippy, who had this thing about going outside, eating lizards, and then vomiting them up on the rug. And I couldn't understand why that was such an important thing for a dog to do. I could see doing this once, maybe. But pretty much every day? Go out, eat a lizard, then throw it up? What could nature possibly have been thinking when it designed this idiot dog?

  So I began my column — and this is very rough paraphrasing — but I said something like: “I was going to write about my dog throwing up lizards on the rug, but then I won the Pulitzer for distinguished commentary. And I don't think I'm allowed to write about that sort of thing anymore. I now need to write about the situation in the Middle East. And the best way to understand the situation in the Middle East is to compare it to a dog who throws up.”

  I wrote the rest of the column about Zippy. By the following week, it wasn't a big deal anymore.

  The Pulitzer will be cited with your name for eternity: “Dave Barry, Pulitzer Prize winner.”

  More than anything, the reason that it's good to win a Pulitzer is that you then don't have to win a Pulitzer. You've won it, and you'll always be identified that way. It's just another prize, really, but it's a prize that everybody recognizes. Whenever I speak before a group, they introduce me by saying that I won the Pulitzer, and everybody nods, as if that means something.

  Were there any topics over the years that were off-limits to you as a syndicated columnist? Newspaper readers are a prudish bunch.

  The obvious ones. For humor, you're not going to make jokes about rape, and you don't make jokes about the Holocaust. And, for a while, you didn't make jokes about terrorism, but now it's okay again. Newspaper readers are, in my view, not as prudish as newspaper editors think they are.

  When my column first began and it was getting fairly wide distribution, editors often perceived it as being a little bit edgy, pushing the envelope a bit. I would get a reaction like: “I don't know about this. I don't know if we can run this.”

  There will always be readers who are immediately offended and want to cancel their subscription, but the odds are that if it's funny, there will be way, way, way more readers who just laugh and enjoy it. The thing is, though, they don't call or write or anything; they don't let the newspaper know they liked it. So columns or jokes that would actually be amusing to people tend to get killed. This is one of the things that have hurt newspapers — as their circulations have begun to decline, they've become more hamster-like in their fear of everything that might offend anybody.

  I'm always amazed when I see something funny in a newspaper.

  It's as if it's not allowed.

  Especially comic strips.

  I know. My god!

  Did you ever feel you could get away with less in a newspaper than you might have in a magazine?

  Absolutely. In fact, that would probably go for any medium outside of the newspaper. You can say things on television that papers would be reluctant to talk about. The tyranny of the one or two humor-impaired people out there who call … well, it's just incredible. Editors just don't like being yelled at. They just don't. And they will react to it.

  Would you have written differently if you were contributing to, say, The New Yorker or Esquire or any other magazine?

  I don't think those magazines would have published me, because I don't think my humor would have ever been viewed as sophisticated enough for The New Yorker. I never had much luck with the city of New York, to be honest. In any way.

  Why do you think that is?

  I don't know. I mean, I just think my humor is viewed as too sophomoric, and too much as guy humor. It's not what New Yorkers like.

  Does this bother you?

  No, not at all. I recognize that there are lots of different kinds of humor, and I think there's sort of a New York — editor attitude, like at The New York Times. Their humor, for a long time, was written by Russell Baker, who was brilliant, and I don't mean to put it down. It just wasn't me. It wasn't wacky dog-poop humor, and that's okay. I mean, they know who their audience is. My column did run in New York, in the Daily News, but only on Sunday. And as far as I could tell, nobody ever read the Daily News on Sunday, including the Daily News editors. Maybe that's why my column was in there.

  Were there any topics that you were afraid to write about? How about religion?

  No, thanks.

  Was that off limits?

  No. I wrote a couple of columns about religion, and I didn't really have much of a problem. My dad was a Presbyterian minister, so I grew up with religion all around me. I myself am not religious — never have been, not even when I was young. So I've always found it mildly amusing, but not in the “It's ruining the world and it needs to be viciously mocked” kind of way. I would write columns about attending St. Stephen's Episcopal Church, in Armonk, New York, as a kid, or a column about Christmas. I would write about religion from that angle, but not from the angle of how I wasn't religious.
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  The things I find fascinating are the types of subject matter that really make people mad and what people really care about. You know, readers are only mildly interested in global situations. Just mildly interested. But then they get really mad about subjects such as cell-phone minutes, or when I criticized Neil Diamond.

  What happened with Neil Diamond?

  I'm still a little worried. I almost feel as if I should start my car with a remote control, because there still may be a Neil Diamond fan out there somewhere. I can kind of relate to Salman Rushdie. He had his problems, but he never said anything bad about Neil Diamond.

  What happened was I once got a call from one of these companies that conduct surveys to find out what songs radio stations should play. This woman played me these seven-second snippets of songs, and I had to say whether or not I liked them. That's all. And I was annoyed, because I didn't want to talk about those snippets. I just wanted to talk about the songs I didn't want to hear on the radio anymore, such as Neil Diamond's “I Am … I Said.”

  So, I wrote a column in which I made fun of that song, but that really wasn't the point of it. The point was this radio's survey. But, man, was there a firestorm! And it lasted forever! Years later, I was watching The Today Show, and Katie Couric was interviewing Neil Diamond. She brought up my criticism of his song, and he laughed. His agent or manager then contacted me and said Neil would like me to come to one of his concerts. I never went. I didn't want to be sitting in front of nine-thousand menopausal women singing “Sweet Caroline.”

  You also made fun of Barry Manilow. You referred to his songs as “weenie music.”

  I did, yes. But I'm not as worried about his fans. To be honest, I think I can take them.

  Reading over your columns again, even going back to the beginning of your career, I found a consistent theme: It seems like you have a deep distrust of government and authority figures.