'Young Hemingway' Wins Sloppy Joe's Look-Alike Contest in Key West

KEY WEST, Fla., July 28, 2026 /PRNewswire/ -- There's a new Hemingway Look-Alike Contest winner in Key West — and for the first time in the competition's 45-year history, he's a "young Hemingway" who looks like author Ernest Hemingway when he lived and wrote on the island during the 1930s.

Chris Dutton of Tampa, Fla., triumphed over 133 other look-alike entrants Saturday, July 25, in the contest finals at Sloppy Joe's Bar — where Hemingway often met friends for cocktails and camaraderie during his Key West residence.

While previous contest winners resemble the white-bearded "Papa" persona Hemingway adopted in his later years, Dutton is a 39-year-old attorney with the dark hair and mustache of the author in his prime.

"I've always had a connection to Key West, and this is extremely meaningful to me," said Dutton of his victory. "I do hope that this will inspire readers, perhaps other young Hemingways, to come compete in the contest."

Look-alike contenders in sportsman's attire paraded across Sloppy Joe's stage during July 23-24 preliminary rounds before a judging panel of former winners. Two dozen prospective "Papas" made it to the finals.

Dutton credited his victory in part to his family's support and the "lucky sweater" he wore onstage — a gift from previous winner David Douglas, president of the Hemingway Look-Alike Society.

During the competition, the society made its annual scholarship presentations to students attending the College of the Florida Keys — bringing its total awarded to date to over $350,000.

Dutton, who won the contest on his seventh attempt, praised the camaraderie among winners and entrants.

"When you start in this contest, you don't know what it's really going to be like," he said. "It's about the brotherhood, the friendship, and that's why we all keep returning."

In addition, he announced his eagerness to work on the society's philanthropic efforts in Key West and Cuba, where Hemingway also lived.

"We really are doing something great here, and I'm going to do everything in my power to keep it going," he added.

Other Hemingway festival events included a "Running of the Bulls" spoof featuring mock bulls on wheels, a "Papas" film evening, the Key West Marlin Tournament, a storytelling challenge and a short story competition directed by author and Hemingway granddaughter Lorian Hemingway.

Pam Morrison of Dunedin, New Zealand, won the short story contest's top honors for "One Small Bird," chosen from over 900 submissions. According to Lorian Hemingway, it impressed the judges for its writer's ability to show the complex depth of emotion that echoed in each character.

"It's a remarkable piece of work with many psychological layers," she said.

During his Key West years, Ernest Hemingway penned classic novels including "For Whom the Bell Tolls " and "To Have and Have Not." The Hemingway Look-Alike Contest and festival was presented in part by the Monroe County Tourist Development Council.

Media Contact: Carol Shaughnessy
Phone: 305-797-0579
E-mail: [email protected] 

SOURCE Sloppy Joe's Bar