Tampa, FL – A Tampa attorney has made history after becoming the first contestant portraying a younger version of Ernest Hemingway to win the annual Hemingway Look-A-Like Contest in Key West.
Chris Dutton, 39, earned the title during the 45th annual competition held at Sloppy Joe’s Bar as part of the city’s Hemingway Days celebration.
The event, which attracts contestants from across the country, honors the life and legacy of the Nobel Prize winning author, who lived in Key West during the 1930s.
Dutton secured the victory after advancing through two preliminary rounds before competing against 23 finalists in the championship round.
More than 130 contestants entered this year’s event. His win came on his seventh attempt after years of participating in the popular competition.
Unlike most previous winners, who typically resemble Hemingway during his later years with a full white beard, Dutton modeled his appearance after the author’s younger years while he was living and writing in Key West.
Contest organizers said contestants portraying a younger Hemingway had previously reached the finals, but none had ever won the competition until this year.
Judging was conducted by past contest winners, who evaluated participants on their resemblance to Hemingway, personality, stage presence and overall ability to represent the Hemingway Look Alike Society.
As the 2026 champion, Dutton will join the Hemingway Look Alike Society and help judge future competitions.
The organization also supports scholarship programs for students in the Florida Keys.
The annual contest remains one of the signature events of Hemingway Days, celebrating the author’s lasting impact on American literature and the Key West community.