Chris Dutton of Tampa, Florida, won the annual Hemingway Look-Alike Contest on July 25 at Sloppy Joe’s Bar in Key West. The 39-year-old attorney defeated 133 other entrants to secure the title in his seventh attempt competing in the event.
Dutton marks the first “young Hemingway” winner in the competition’s 45-year history. While past winners resemble the white-bearded persona of the author’s later years, Dutton entered with the dark hair and mustache that Hemingway sported while living in Key West during the 1930s.
The three-night competition featured two preliminary rounds on July 23 and 24, where contestants in sportsman’s attire paraded across the stage. A panel of former winners evaluated the 134 total entrants, selecting two dozen finalists for Saturday’s concluding round.
Dutton attributed his victory to support from his family and a sweater gifted to him by David Douglas, president of the Hemingway Look-Alike Society. He expressed a desire to inspire other readers to compete and stated his intent to participate in the society’s philanthropic efforts in Key West and Cuba.
During the festival, the Hemingway Look-Alike Society presented annual scholarships to students at the College of the Florida Keys. The organization has awarded more than $350,000 in total scholarship funding to date.
The contest was part of a broader festival honoring the author, who wrote classic novels such as “For Whom the Bell Tolls” and “To Have and Have Not” while living on the island. Festival events included a mock “Running of the Bulls,” the Key West Marlin Tournament, a film evening, and a short story competition directed by the author’s granddaughter, Lorian Hemingway.
Pam Morrison of Dunedin, New Zealand, won the short story contest for her entry, “One Small Bird.” Lorian Hemingway noted that Morrison’s work was chosen from more than 900 submissions for its portrayal of emotional depth and psychological layers.
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