Chris Dutton became the first younger-styled winner of Sloppy Joe’s long-running Hemingway contest, linking a familiar festival ritual to the author’s earlier image.
Sloppy Joe’s Bar announced that Chris Dutton of Tampa, Florida, won the 2026 Hemingway Look-Alike Contest after defeating 133 other entrants in the finals on Saturday, July 25, at the Key West venue. The result marked the first time in the competition’s 45-year history that the winner represented a younger version of Ernest Hemingway rather than the white-bearded “Papa” persona associated with the author’s later years. It also underscored how the contest continues to anchor Key West’s annual celebration of Hemingway’s life and connection to the island.
Dutton, a 39-year-old attorney, was described by Sloppy Joe’s as having the dark hair and moustache associated with Hemingway in his prime. The contest took place during a three-night programme of Hemingway festivities, with preliminary rounds held on July 23 and 24 before the final judging on July 25. Former contest winners served as judges, and two dozen entrants advanced to the final round from a field of 134 aspiring look-alikes.
The event’s format combined performance, appearance and the social rituals that have shaped the contest over time. Entrants in sportsman’s attire paraded across the Sloppy Joe’s stage during the preliminary rounds, while Dutton credited his family’s support and a sweater given to him by previous winner David Douglas, president of the Hemingway Look-Alike Society. Dutton won on his seventh attempt and said the contest’s appeal extended beyond the competition to the friendship and camaraderie among participants.
The wider festival also carried a philanthropic element. During the competition, the Hemingway Look-Alike Society presented annual scholarships to students attending the College of the Florida Keys, bringing the total value of its awards to more than $350,000, according to the release. Dutton said he was eager to support the society’s philanthropic efforts in Key West and Cuba, two places associated with Hemingway’s life.
The result gives Sloppy Joe’s a fresh focal point for an established cultural event without severing its connection to the tradition that made the contest recognisable. Dutton’s appearance places Hemingway’s earlier public image alongside the familiar older “Papa” character, while his victory adds another chapter to a competition built around literary memory, local history and participation. For Sloppy Joe’s, the 2026 contest again positioned the bar as the setting where Key West’s Hemingway celebrations meet a continuing community ritual.
