A Barry Funny Guy

Humor columnist and author Dave Barry dishes about life in his native Westchester and beyond.

Good morning! Today is Wednesday, February 9, and you are reading today’s section of Examiner+, a digital newsmagazine serving Westchester, Putnam, and the surrounding Hudson Valley.

Armonk native Dave Barry knows funny. In fact, it’s his job. The humorist wrote a weekly column for the Miami Herald for more than 20 years, with his wit and prose earning him a Pulitzer in 1988. Barry has since published more than 30 books and even had a sitcom based on his life.

Examiner+ caught up with Barry to discuss life in Westchester, his fond memories of “Barmonk,” and his one and only humor column he wrote for the Pleasantville High School newspaper.

Examiner+: What was it like to grow up in Westchester County?

Dave Barry: Well, it was good for me. I grew up, and this was millions of years ago, in Armonk. The town I was born and raised in was just a little village then. It was the best of both worlds because we were a little town. Literally, everybody knew everybody. So, the kids could run free and we knew everybody we saw on the street. But also we were 30 miles from New York. We could get to White Plains and get the train to “the big city.” So we thought we were sophisticated, but we lived this bucolic, happy life — the kids did, anyway, in Armonk. I have really good memories of that time.

It’s really different now. I’m sure that somebody’s having a good time in Armonk as we speak, but whoever that is has way more money than anybody when I was there. The people who lived literally on my street; one guy was an advertising executive, one was a Nestle executive. But also, there was a carpenter, a plumber, a guy who ran a stationery store — let’s say, regular blue-collar people. I don’t think there’s a lot of that in Armonk anymore. It’s become a high-end, pony town. And I’m sure there are a lot of wonderful people there, but it’s not what it was when I grew up.

E+: You attended Pleasantville High School and you wrote humor columns for the school newspaper. What were people’s reactions to your columns?

DB: Well, first of all, I think I only wrote one because the editor of the paper was a friend of mine named Tom Parker, who only became the editor of the paper so that he could put it on his application for college, which worked. He got into Yale. But he didn’t really didn’t do it out of a passion for journalism.

I wrote a column that I thought was hilarious, and I honestly don’t remember if anybody else did, or if anybody even read it. I do remember what it was about. The senior boys had a tradition: back then we would go to a field and drink a bunch of beer — which I want to stress is illegal and young people should never do this — and then play football. It was called, “Load Ball,” and it was just a ridiculous drunken running-around, falling-down thing.

But I wrote an account of the Load Ball game as though it was a real sporting event for the Pleasantville High School paper. I can’t remember anything else about it other than a, I thought it was hilarious, and b, as far as I know, nobody but me read it. Certainly, nobody in the administration at Pleasantville High School was even vaguely aware of what it was about. I imagine everybody who could punish me is by now dead. so I’m glad I got that off my chest.

E+: Even though they might not have read your column, your fellow students at Pleasantville found you funny, because you won class clown of Pleasantville High School, class of 1965.

DB: That is correct. I did. Thank you for doing your research on that. I want to point out we were very gender-oriented back then; the Spanish-American War was still going on. So we were not as aware as we are today, of course of gender issues, but we had a male and a female for each category. I was the male class clown. The female class clown, who should get credit, was Toni Flood, Antoinette Flood. I believe, pretty sure, you might want to check the record on that. But yes, I was acknowledged by my peers as the class male funny person. That was probably my biggest achievement in Pleasantville High School.

E+: Be honest, what was more exciting: winning class clown or winning a Pulitzer?

DB: It’s six of one — really very similar experiences. Except as I recall, the Pulitzer Prize people don’t have a male and a female award for best column. I’m sure that if they did, Toni Flood would’ve been in the running for it. I just want to give her credit.

E+: In your writing, you’ve mentioned that you and your family were parishioners of St. Stephen’s Church in Armonk, and that you have many memories there. Were there any other places in Armonk or Westchester that you used to frequent and have memories from?

DB: Yeah, but they’re all gone. All the stores in Armonk that I used to go to, that we used to hang out at, have all changed and become tonier, I guess is the word. There used to be this place in Armonk called Schultz’s Cider Mill. It was famous and another place called The Log Cabin, also famous. Both gone now. So I’ve got to say, it looks similar, the town, when I go into it, which is once every few years, I drive through it.  

The schools are still there. Wampus Elementary, where I went to school, is still there, and Harold C. Crittenden Middle School is still there. I remember when Harold C. Crittenden was actually the superintendent of schools. So that all brings back those old, what-a-time-to-be-a-kid vibes.

But actually, most of the places are gone. There were millions of bars in Armonk back when I was a kid. Our major industry was bars. The joke was it was “Barmonk.” There were at one point, the numbers are vague in my mind, something like 2,000 people and 20 bars. Because the legal drinking age in Connecticut was 21, and in New York, it was 18. And we were right over the state line, so it was a very popular activity. I remember all these bars, but I don’t think any of them are there anymore.

E+: Besides the taxes, do you think there’s anything particularly funny about Westchester?

DB: I don’t know. I’m not there. I’ve been out of it really since the ’60s. It just seems like it’s gotten more and more and more Westchester-y and more expensive and less rural all the time. It’s so beautiful, but it feels like a completely foreign environment to me now.

E+: Foreign because you live in Miami and you’ve lived there for many years now.

DB: Yeah. Well, because I live in Miami, all of the United States is foreign to me. My joke is I moved to Miami in 1986 from the United States and yet, I’m very comfortable here and I’m used to here.

E+: You said haven’t lived in Westchester in years, but you said you still find yourself back here every few years. And those times that you have come back, you’ve given back to the community that raised you. You had events here in 2011 and 2017 where proceeds went to Pleasantville High School and St. Stephens Church. What has made you continually come back to support your hometown?

DB: Well, because they asked me to. No, the 2011 thing was just, I was on a book tour and it just seemed like it fit right in. I did actually a fun event at Pleasantville. I do remember that because I have very fond memories of Pleasantville High School and that was nice.

St. Stephen’s has deep, deep memories for me. My family grew up there. My dad was a minister, but he ran a social work agency in New York City. He didn’t have a parish, but his close friend — my dad was actually Presbyterian — but his close friend, Ken Morris, was the pastor at St. Stephen’s. And so we all went. We got baptized there and took communion there and did the Christmas pageants there at Sunday school and stuff like that. So I was really happy to go back and do an event for them.

E+: Is there anything that you have yet to write about or still want to write about?

DB: Oh my God. I don’t know. It’s like every day when you’re trying to write something, it’s like, “What haven’t I written about?” And so, no, it’s just, I generally write about what’s going on. At the moment, I’m trying to finish this annual thing I do. The year in review that runs in the Washington Post and some other papers, Miami Herald, where I work. So there, I’m just basically taking the events of the year and trying to make them funny, talk about a dismal task. Everybody always says, “Oh, you must have so much to work with.” And I think, yeah, but it wasn’t funny. What was funny about it? That’s my job. So the answer to your question is really, I never have anything to write about. So I just write and eventually something appears.

But it’s not like, I’ve never been a person who went around thinking I have this message I need to deliver, or I have these thoughts that people need to know. That has never been me. I really have nothing to say. I’m kind of worthless. Maybe I can amuse people and they’ll like me more. That’s why I became class clown of Pleasantville High School — and that’s why I’m still writing humor all these centuries later.

E+: Besides your year in review, what’s next for Dave Barry?

DB: Well, I’m trying to finish a novel. Every now and then, I write a novel and they’re always set in South Florida, and this is, as well. I’m nearing the end of it, and it’s going to come out in 2023 if I understand the publisher correctly. But I’m close to finishing it, I hope, if I can think of an ending. If anybody reading this article has a good ending for me, just send it on over and I will give you a little acknowledgment somewhere.

E+: Dave, what’s the best way for people to connect with you?

DB: Oh, I don’t want them to do that.

E+: Sorry. We’re asking in the age of Instagram. Don’t worry. We’re not blasting your phone number or your email address.

DB: I’m on Twitter. But I only tweet once a month. I’m not a frequent tweeter. And then I have a blog that I put stuff on almost every day, but it’s not original things. It’s more like when I used to write a column, a lot of the times the topic of the column was some ridiculous… somebody found a snake in their toilet or somebody blew up a cow and I would write a column about it. Now I don’t write columns as much anymore, but I still put the articles up on my blog. So it’s basically a bunch of links to ridiculous things that have happened. So there’s that.

But people can just rest assured that they don’t need really to keep up with me because I’m never saying anything important.

Erin Maher is a writer and Westchester native. She has written on a myriad of topics, including life as a millennial and tennis. When not writing, Erin can be found on the tennis and pickleball courts or lovingly scrolling through pictures of dogs on Instagram. For more of her musings, visit erinmaherwrites.com, and follow her on Instagram @erinmaherwrites and Twitter @erinmaherwrites.

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