Chris Dutton wins Key West Hemingway look-alike contest on seventh attempt

Chris Dutton won the 45th Hemingway Look-Alike Contest on his seventh attempt
He is the first ‘Young Hemingway’ to win the competition
Dutton emerged from 134 registered contestants to claim the title
The scholarship program has awarded more than $350,000 to Florida Keys students
Hemingway lived in Key West during the 1930s and wrote many famous works there

Perseverance paid off as Chris Dutton made history becoming the first ‘Young Hemingway’ ever to win Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest.

The 39-year-old lawyer from Tampa captured the title, joining a brotherhood dedicated to preserving Ernest Hemingway’s legacy through friendship, tradition and service. Dutton’s road victory was far from easy. He emerged from a field of 134 registered contestants, in two preliminary rounds before defeating 23 other finalists to claim the title on his seventh attempt. While most contestants portray the older, white-bearded version of Hemingway, Dutton embodies the younger writer who lived and worked in Key West during the 1930s. Other ‘Young Hemingway’s’ had reached the finals over the years, but none had ever won until now.

The judges, each a former Look Alike winner known affectionally as a ‘Papa’, look for more than a familiar face. They evaluate resemblance to Hemingway, stage presence, character, and the ability to represent a society devoted to preserving the celebrated author’s legacy. Twenty-four finalists each had one minute to make their case before the top five earned 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. The Hemingway Look-Alike Society’s scholarship programme has awarded more than $350,000 to Florida Keys students.

Chris Dutton shared: “It’s about the brotherhood, the friendship, and that’s why we all keep returning. I haven’t completely digested it yet. But I’m ready. Ready to get to work.”