2026 Hemingway Look-Alike Contest Makes History

39-year-old lawyer from Tampa Chris Dutton has become the first 'Young Hemingway' ever to win Sloppy Joe's Annual Hemingway Look-Alike Contest.

Dutton emerged from a field of 134 registered contestants, via two preliminary rounds before defeating 23 other finalists to claim the title on his seventh attempt.

Most contestants portray the older, white-bearded version of Ernest Hemingway, but Dutton embodies the younger writer who lived and worked in Key West during the 1930s. Other Young Hemingways have reached the finals in previous years, but none have ever won.

The judges for the 45th iteration of the prize, each a former Look-Alike winner evaluate resemblance to Hemingway, stage presence, character, and the ability to represent a society devoted to preserving the author's legacy. Each of the 24 finalists have one minute to make their case before the top five earn two additional minutes on stage.

Dutton credited seven years of unwavering family support, a keepsake from a past winner, and one well-kept secret for helping him capture the prestigious title.

"Papa David Douglas gave me this sweater,” said Dutton, of the contest's 2009 winner. “I've had it for a few years and I never told anybody. The competition is about the brotherhood, the friendship, and that's why we all keep returning."

Dutton now moves from contestant to judge, helping select future winners while supporting the Hemingway Look-Alike Society's scholarship program which has awarded more than $350,000 to Florida Keys students.

Hemingway lived and wrote some of his most famous works in Key West through much of the 1930s and was a regular at Sloppy Joe's Bar where the contest was held. The annual contest is the signature event of the six-day Hemingway Days celebration honoring the 127th anniversary of his July 21 birth.