Dave Barry’s Journey from Class Clown to Fame and Fortune
Pleasantville High School’s self-proclaimed second most-famous alumnus is coming home.
Humorist Dave Barry, a 1965 Pleasantville High School graduate, will be on hand for a talk and book signing at the White Plains City Center Barnes & Noble on Wednesday, April 6, at 7 p.m. Barry is promoting his new book, “I’ll Mature When I’m Dead,” a collection of essays about adulthood.
As part of Barnes & Noble’s book fair, each time a supporter mentions the book at the checkout counter during the day, a percentage of the sale will be donated to Pleasantville High School. Barry will also be at the Jacob Burns Film Center tomorrow to screen “This Is Spinal Tap,” one of his favorite movies.
Barry said he is looking forward to returning to his old stomping grounds.
“I imagine there’s still some gum wads in the drinking fountain at the high school,” Barry said.
Barry actually grew up in Armonk but in the ’60s, before Byram Hills was built, students headed to Pleasantville for high school. He said it was an adventure getting to take the bus to the village each morning.
“I really liked it. Initially I was a puny, glasses-wearing skinny kid, but by the time I was a senior I was a stud,” he joked. “Okay, I wasn’t, but I had a lot more friends.”
Barry, proud to have been voted class clown of his graduating class, said he has positive memories of Pleasantville High School. He has occasionally mentioned the school in his columns, and in the past received warm responses from teachers who weren’t initially fond of him.
“It was for general wise-assery,” Barry of some teachers’ dislike of him. “Being puny and wearing glasses, I was not going to win friends, so I tried to be funny.”
One popular prank was for upperclassmen to find somebody’s Volkswagen, pick it up and place it on the school’s steps.
“We were doing that while the Russians were getting ahead in space,” Barry said.
His career as an essayist and columnist started out in Pleasantville. He wrote humorous essays in class, and his English teacher, Gloria Adams, would read them aloud, provided she didn’t reveal who wrote them. He also wrote for the Green Quill, the school’s yearbook.
“That was eye-opening,” Barry said. “You could argue that was the beginning. I realized that it’s fun to make people laugh.”
After graduating high school, Barry went to Haverford College. After a series of jobs, he landed at the Miami Herald, where he’s worked since 1983. Along with being a columnist, Barry has also published more than 30 books. His columns were the basis for a sitcom, “Dave’s World,” that premiered in 1992. Despite his fame and fortune, Barry said he considers Gavin McLeod, of “The Mary Tyler Moore Show” and “Love Boat” fame, to be Pleasantville’s most famous alumnus.
“We have to give Gavin the lead,” he said. “He was on ‘Love Boat.’ How many people can say that? He’s got me beat thoroughly.”
Barry said he doesn’t have any family in the area any longer, but still has friends and occasionally returns for class reunions. While the area looks similar to when he was growing up, he said it feels busier, as though it’s closer to New York City than it used to be.
“Back then we felt a little more distance,” Barry said. “We felt like we were our own town.”
Barry said he would tell high school students with writing aspirations to read and write as much as possible.
“The more you write, the better you get,” he said. “Don’t try to copy people; it’s not usually a route to success and satisfaction. And have a real job, because you’re not going to make a living writing at first.”
Adam has worked in the local news industry for the past two decades in Westchester County and the broader Hudson Valley. Read more from Adam’s author bio here.