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Florida helicopter pilot crowned new "Papa" at Hemingway look-alike contest in Key West

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FLORIDA KEYS - A 71-year-old white-bearded Florida man has won the 2024 Hemingway Look-Alike Contest, a highlight of Key West's annual Hemingway Days festival that ended Sunday at the iconic Sloppy Joe's Bar.

The yearly celebration concluded with a birthday cake to honor the 125th anniversary of Ernest Hemingway's July 21 birth.  

David "Bat" Masterson, a retired helicopter pilot from Daytona Beach, triumphed over 121 other entrants in the three-round contest that concluded Saturday night at Sloppy Joe's. The bar was a frequent hangout for renowned author Ernest Hemingway, who lived and wrote in Key West for most of the 1930s.

"Like Hemingway, I have a thirst for life and a quest for adventure," said Masterson, who earned the victory on his 10th attempt. "I like to fly and ride motorcycles and jump out of airplanes and that sort of stuff.

"And Hemingway was a very adventurous man, and I admire him for that," he added.

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David "Bat" Masterson, center, gets smooches from past Hemingway Look-Alike Contest winners Jon Auvil, left, and Gerrit Marshall, right, Saturday, July 20, 2024, at Sloppy Joe's Bar in Key West. Andy Newman/Florida Keys News Bureau

The Look-Alike Contest finals followed preliminary rounds Thursday and Friday. Many entrants wore casual sportsman's garb or thick fisherman's sweaters, attempting to emulate the rugged "Papa" persona that Hemingway adopted in his later years.

Saturday night, competitors including Leslaw Jedrysko of Nowy Targ, Poland, paraded across Sloppy Joe's stage and took turns speaking as hordes of spectators waved signs and applauded their favorites.

Masterson wowed the judges, who were all previous contest winners, by singing a themed parody of the Garth Brooks hit "Friends in Low Places."

The new "Papa" said he writes a little bit and shares several other traits with Hemingway.

"I grew up hunting and fishing," Masterson said. "My father was a lot like Hemingway's father. He taught me all about the outdoors and about fishing and hunting, and taking care and being a good steward of our environment."

The history of Hemingway Days in Key West  

In the rowdy crowd at Sloppy Joe's was celebrity chef Paula Deen, whose husband Michael Groover won a look-alike title in 2018.

Hemingway Days salutes the vigorous Key West lifestyle and literary talent of the author who wrote classics including "For Whom the Bell Tolls" and "To Have and Have Not" during his years on the island.

Festival events included a quirky "Running of the Bulls" spoof, readings and presentations, and the Key West Marlin Tournament that recalls Hemingway's passion for Florida Keys fishing.

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