A 71-year-old white-bearded Florida man won the 2024 Hemingway Look-Alike Contest, a highlight of Key West’s annual Hemingway Days festival that ended July 21, which was the 125th anniversary of Ernest Hemingway’s birth.
David “Bat” Masterson, a retired Monroe County Trauma Star 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. Hemingway also was a very adventurous man, and I admire him for that.”
Many look-alike contestants wore casual sportsman’s garb or thick fisherman’s sweaters, attempting to emulate the rugged “Papa” persona that Hemingway adopted in his later years.
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. The look-alike contest raises money for Key West scholarships.
Festival events also 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.
