1987 Winner: Jack Waterbury

Jack Waterbury has the best of three worlds. He summers in Maine. He winters in Key West. And he’s one of the fortunate few bearded boys who can call himself Papa for the rest of his life. Add to all that, he has a way with making a lasting impression on women. Praised a beautiful waitress at Sloppy Joe’s Bar, “I just love that horny, old goat!”

As colorful a character as they come, Jack hesitates a couple seconds before he answers a question about any memorable anecdotes from his years as a wannabe Papa and judge at the Hemingway Look-Alike contest.

“I should think about that a little before I get in trouble,” Jack said. Then he thinks about it a little before he gets in trouble, spinning this sly tale about one of his early attempts to win the contest.

“There was this pretty lady I met before the preliminary round at Sloppy Joe’s, and I took her out drinking later at the Pier House. I guess I got fresh with her, and it didn’t work. I didn’t know who she was until the next day…and she was one of the judges! I was finished! It was two years before they let me come back.”

Those who know him don’t take everything he says with a grain of salt. They take it with a barrel of salt. The dear reader is advised to do so here.

“The alleged incident turned out to be a minor blip on Jack’s rowdy-but-ready pursuit of the ultimate Papa enshrinement. Referring to his crowning in the 1987 event, he sighs, “They finally recognized that I was the best.”

He thinks about that a little, then adds, “Actually, I was pretty lucky. I won it back when it was easy to win.”

Jack’s Hemingway genes came honestly.

“My father was so much like Hemingway, it was just unbelievable. Same look, same age. He was the same crazy kind of guy―married five or six times. He wasn’t a writer―he was a New Jersey real estate man―but he sure loved boats.”

A talk with Jack is like a meandering trip through a confusing conversational maze. For example, his take on his beard woes.

“I said I could look more like Hemingway than a lot of those battle farts, but I couldn’t grow a decent beard. I worked for the airline then, and you weren’t allowed to have a beard, so I took my vacation right before the contest, which gave me three weeks to grow a beard. Not a very good one, though.”

That puts a lot of pressure on a beard, doesn’t it?

“Yes,” he answered with a laugh, “so I told them when I won it that I had to quit my job so I could grow a beard.”

Did he really quit?
“Yeah, I did, but not so I could grow a beard.”

Born in Little Silver, New Jersey, Jack moved to Key west in 1979, citing two major reasons.

“I guess it was the divorce, and I sure wanted a boat.”

And not necessarily in that order.

“I wanted to live on the boat, but I don’t like hot weather, so I thought I’d better come down and try it out to see if I could stand it. I came down with a bunch of crazy kids. We listened to Jimmy Buffett music all the way down.”

Not surprisingly, Jack immediately fell in love with Key West.

“Especially the craziness and the reef,” he said, exposing his Caribbean soul. “I love to spear fish.”

Jack solved his hot weather dilemma by dividing his time between Key West and his Penobscot Bay home along the Maine coast near Bar Harbor and Acadia National Park.

“Local people call it the Lobster Capital of the World,” Jack said with a modicum of Yankee civic pride.

He wanders from the Southernmost city to the Northeasternmost State in his camper, stopping off en route to visit friends, including those from the Hemingway Look-alike Society.