Seven tries. One lucky sweater. Perseverance paid off July 25 in Key West, as Chris Dutton made history becoming the first “Young Hemingway” ever to win Sloppy Joe’s annual Hemingway Look-Alike Contest. The 39-year-old lawyer from Tampa joins a brotherhood dedicated to preserving Ernest Hemingway’s legacy through friendship, tradition and service.
Dutton 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.
And 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 Hemingways” had reached the finals over the years, but none had ever won — until now.
The judges, each a former look-alike winner known as a “Papa,” evaluate resemblance to Hemingway, stage presence, character and the ability to represent a society devoted to preserving the celebrated author’s legacy.
After his first appearance at the look-alike contest, Dutton said he discovered what keeps generations of contestants coming back: the friendships. In 2019, a past Papa invited him on a trip to Cuba, where Hemingway also briefly lived. Experiences like that, he said, revealed the true spirit behind the competition.
“It’s about the brotherhood, the friendship and that’s why we all keep returning,” Dutton said.
And his new role is only beginning. He now moves from contestant to judge, helping select future winners while supporting the Hemingway Look-Alike Society’s scholarship program, which has awarded more than $350,000 to Florida Keys students. He also becomes one of the tradition’s ambassadors, helping ensure Hemingway’s enduring influence continues for future generations. Dutton said he would do everything in his power to keep the tradition going.
“I haven’t completely digested it yet. But I’m ready. Ready to get to work,” Dutton said.
Bulls, berets take Duval
Beards, berets and wooden bulls rolled through Old Town Key West the afternoon of July 25 during the 45th annual ‘Running’ of the Bulls event, one of Hemingway Days’ most recognizable traditions.
Calling it a “run” is a stretch. While the “Papas,” as Hemingway was often called, sauntered down the one-block route, the crowd erupted in cheers just like it was the real deal in Pamplona, Spain.
Dressed in crisp white clothing with bright red berets and bandanas, past winners of the Hemingway Look-Alike Contest joined hundreds of “Papas” for the signature stroll down some of Key West’s most famous streets. They set out from Sloppy Joe’s Bar, crossed Duval Street, looped through Old Town and returned to the bar where Hemingway often hung out.
Five bulls — wooden sawhorse replicas mounted on wheels — joined in on the makeshift run, adding a bit of levity.
