Key West, Fla. – Chris Dutton, a 39-year-old attorney from Tampa, has made history by becoming the youngest winner and the first "Young Hemingway" to claim the title at the 45th Annual Hemingway Look-Alike Contest. The event, held at Sloppy Joe’s Bar, is a signature part of the six-day Hemingway Days festival celebrating Ernest Hemingway's legacy in Key West.
Youngest Winner in Contest History
Dutton emerged victorious from a field of 134 registered contestants, ultimately defeating 23 finalists to secure the coveted title. This win marks a significant achievement, as previous "Young Hemingway" contestants had reached the finals but never won. Dutton, who embodies the younger Hemingway of the 1930s, achieved this on his seventh attempt at the contest.
The judges, comprised of former contest winners known as "Papas," assess contestants on resemblance to Hemingway, stage presence, character, and their ability to represent the society dedicated to preserving the author's legacy. Dutton's victory was attributed to seven years of family support, a special sweater passed down from a past winner, and his perseverance.
A Tradition of Friendship and Legacy
The Hemingway Look-Alike Contest, which began in 1981, draws participants and fans globally. It celebrates Ernest Hemingway's enduring connection to Key West, where he lived and wrote many of his famous works. Dutton emphasized that beyond the competition, the true spirit of the event lies in the friendships and brotherhood it fosters among participants.
He recalled an invitation to Cuba from a past "Papa" in 2019 as an example of the deep connections formed through the contest. Dutton plans to transition from contestant to judge, supporting the Hemingway Look-Alike Society's scholarship program, which has awarded over $350,000 to Florida Keys students. His commitment is to help ensure the tradition continues for future generations.
The Hemingway Days festival honors the 127th anniversary of the Nobel Prize-winning author's birth. The contest itself is a key attraction, bringing hundreds of "Papas" to Key West each year. For more details on the festival and its events, readers can visit the WLRN Keys report.
The contest rules and history are part of a larger narrative of literary celebration in the Keys. Information about Ernest Hemingway's life and works, particularly his time in Key West, can be found through various historical resources, including those that document the annual Hemingway Days festival.



