‘Old Guys Rule’ at Hemingway Look-Alike Contest
July in Key West means Hemingway Days, the island’s annual celebration of Ernest Hemingway’s birthday, and one of the festival’s most popular events is Sloppy Joe’s “Papa” Hemingway Look-Alike Contest. Large men sporting beards, some wearing khaki pants held up with rope belts, wander the streets and occupy the barstools of Key West’s watering holes, each hoping to be named the year’s look-alike winner.

The late Tom Chadwick is fondly remembered by his fellow Hemingway look-alikes and fans. (Photo courtesy of the Hemingway Look-Alike Society)
The Look-Alike Contest is unlike most other contests in that rotund seniors can enter repeatedly, and most don’t win on their first try. One of the most persevering contestants was Tom Chadwick, who passed away last August. He’s probably best described in the tribute here, written by his and his wife’s good friend, Bunny Carey.
“He was in last year’s contest, and this year would have been 29 years in a row he participated. Tom was known as the ‘Horny Papa,’ since he always wore a Viking hat with horns in the contest. Last year he donated this hat to be auctioned off for the Hemingway scholarship drive, fetching $400. It is now on a plaque, with his name, at Sloppy Joe’s Bar in Key West.
“Tom was an annual favorite when he went onstage and announced, ‘Well, how do you like me so far?’ We not only liked him, but loved his enthusiasm and zest for life. Although he never won, he was always a winner, and all who knew him loved him.
“I like to recall Tom sitting at Sloppy Joe’s Bar, as he did many times, saying, ‘I’ll have another!’ Of course, he always bought drinks for everyone else, as he was also a great ‘Papa.’ I’d like to think he’s on a cloud with other lost look-alikes, along with the original, one-and-only Ernest Hemingway — with drinks on the house for all.

Shown here participating in Sloppy Joe's "Running of the Bulls," Tom (center) loved camaraderie and cocktails -- and that's no bull! (Photo courtesy of the Hemingway Look-Alike Society)
“Tom was the true reflection of ‘The Old Man and the Sea.’ He was attracted to the sea as a young man and served in both the U.S. Navy and the U.S. Coast Guard. He passed away as a sailor at sea while on a Caribbean cruise with his wife at the young age of 84.
“I met Tom on a cruise over 20 years ago. He was at the bar, and his (first) words were, ‘Hi, I’m Tom. Can I buy you a drink?’
“His memory is one that makes my heart smile, and I’ll drink to that.”
I never knew Tom Chadwick, but I have had the privilege of knowing many other participants in the Look-Alike Contest — some winners, some perennial hopefuls.
Among them are previous winners Jack Waterbury, a former airline pilot who still has a roguish twinkle in his eye; Bill Young, a gentle man and a gentleman who actually met Hemingway in Spain; and Fred Johnson, longtime guiding spirit behind the look-alikes’ fraternal society.

Each year "old guys rule" in the "Papa" Hemingway Look-Alike Contest. (Photo by Andy Newman, Florida Keys News Bureau)
I also recall some who have competed for many years, returning annually to enjoy the camaraderie of their fellow contestants, and to try once again to be known as an Ernest Hemingway look-alike winner.
This year’s Look-Alike Contest will be held, as always, at Sloppy Joe’s, beginning July 19. The finals are scheduled for July 21, when yet another stocky, bearded senior citizen will be named the winner. So if you’re in town during the Hemingway Days festival, join the crowd at this unusual competition — a big-as-life example of the popular contemporary catchphrase “Old Guys Rule.”

