The competition is a highlight of the island's Hemingway Days festivities, celebrating the writing talent and colorful lifestyle of the man who penned literary classics while living in Key West during the 1930s.
Look-alike hopefuls from as far away as Australia and Norway are vying for victory during the three-night competition at Sloppy Joe's Bar, where Hemingway often drank with friends.
Cheered by crowds of spectators, Thursday’s aspiring "Ernests" took turns parading across Sloppy Joe’s stage. They were scrutinized by a judging panel of former winners including 2017’s Richard Filip of Fayetteville, Texas.
Most entrants chose to wear the sportsman's attire or safari togs characteristic of Hemingway.
Many are repeat contenders including Michael Groover, husband of celebrity chef Paula Deen (00:28-00:37), who was on hand to cheer him on.
The contest's second preliminary round is set for Friday. The 2018 winner is to be chosen Saturday night -- the 119th anniversary of Hemingway’s July 21 birth.
Hemingway Days continues through Sunday with events including an offbeat "Running of the Bulls," the three-day Havana Club Key West Marlin Tournament and a historic tour of Hemingway sites in Key West.