Hemingway look alike contest 2025

Part of winning the Hemingway Look-Alike Contest involves convincing a group of past winners why you should earn the title. That’s what 69-year-old Tim Stockton of Key West managed to do on his sixth attempt. His compelling story about Hemingway helped him clinch the title on Saturday, July 25, 2025, in Key West at Sloppy Joe’s Bar.  (Mark Hedden / Florida Keys News Bureau)

Hemingway Look-Alike Winner, Tim Stockwell of Key West, Florida, celebrates his victory with a group of past winners. The contest took place in Key West on July 26, 2025, at Sloppy Joe’s Bar, a frequent hangout of Ernest Hemingway.  (Mark Hedden / Florida Keys News Bureau)

Hemingway Look-Alike Winner Tim Stockwell of Key West, Florida, received congratulatory kisses from former winners Gerrit Marshall (left) and David “Bat” Masterson (right) after capturing the coveted title at Sloppy Joe’s Bar on Saturday night, July 26, 2025. Stockwell triumphed over more than 130 entrants in the highlight event of the annual Hemingway Days celebration.  (Mark Hedden / Florida Keys News Bureau)

Keefer Haynie, a feisty six-year-old from Baton Rouge, Louisiana, rolled up his sleeve to show a panel of judges his Hemingway inspired temporary tattoo during the Hemingway Look-Alike Contest in Key West, Florida, July 26, 2025. The quirky contest brought out men of all ages, to compete for the title of “Papa.”  (Mark Hedden / Florida Keys News Bureau)

Being a judge in the Hemingway Look-Alike Contest has one important requirement — you must be a past winner. This panel of judges patiently listened to more than 130 men state their case as to why they should win and crowned a champion on Saturday, July 26, 2025, in Key West, Florida.  (Mark Hedden / Florida Keys News Bureau)