It’s revered as legendary author Ernest Hemingway’s 1930s hangout. Known as the 1981 birthplace of the internationally renowned Hemingway® Look-Alike Contest. Famed as a Key West landmark and a must-see stop for virtually every visitor to the island city.
And on May 5, 2022, Sloppy Joe’s Bar marks 85 years at its iconic home at 201 Duval St., the corner of Duval and Greene streets.
Sloppy Joe’s was a favorite hangout in 1938 just as it is today. (Photo by Arthur Rothstein, courtesy of the Library of Congress)
The story of how it got there — and its enduring connection to Hemingway — is as intriguing as the plot of one of the author’s own tales. Although Keys Voices has explored aspects of Sloppy Joe’s history before, the anniversary provides a perfect reason to revisit it.
Interestingly, the bar is actually more than 85 years old. It first opened its doors at 428 Greene St. on the day Prohibition was repealed in 1933.
Since Key West was a haven for free-thinkers even in the ‘30s, Prohibition had been regarded as an amusing exercise dreamed up by the government — and Joe Russell was just one of the enterprising individuals who operated illegal speakeasies during the so-called “dry” years. Even Hemingway slipped over to Russell’s on occasion to buy illicit liquor, and the two struck up a lasting friendship.
Joe Russell was a charterboat captain and rumrunner who became Hemingway’s boat pilot and fishing companion for 12 years. Ernest called him “Josie Grunts” and used him as the model for a character in his classic novel “To Have and Have Not.”
Joe’s newly legal bar was a freewheeling place whose attractions included gambling and pool tables in the rear — and it had several names before being given the now-famous moniker of Sloppy Joe’s. (Hemingway has been credited with suggesting the name, BTW, after a spot in Havana.)
Of course, Ernest and his “Mob” of cohorts were enthusiastic regular customers. The “Mob” was a blend of American literary giants and local residents who wrangled, drank, and philosophized at the bar, never knowing they were building a legend.
Hemingway look-alike Joe Maxey (left) gets a playful smooch from a fellow “Papa” outside Sloppy Joe’s after winning the 2019 look-alike contest at the famed bar. (Photo by Andy Newman, Florida Keys News Bureau)
Sloppy Joe’s moved down the street to its current location on May 5, 1937, after Joe Russell’s landlord raised his rent from three dollars per week to a whopping four.
Not happy about the rent hike, Russell quietly spent $2,500 to purchase the former Victoria Restaurant at the corner of Duval and Greene streets — a structure built in 1917 that incorporated beautiful Cuban tilework, ceiling fans and jalousie doors.
The moment his lease at 428 Greene St. expired, while the landlord was out of town, he sprang into action.
In singular Key West fashion, the bar never actually closed during its sudden relocation. Recruited by Joe, customers simply picked up their drinks and carried them, along with everything else in the place, over to Sloppy Joe’s new home. Service resumed with barely a blink.
When Hemingway left Key West in late 1939, although few people knew it, many of his possessions remained — and ultimately wound up stored in a back room behind Sloppy Joe’s long horseshoe-shaped bar.
Sloppy Joe’s is an enduring landmark at the corner of Duval and Greene streets. (Photo by Rob O’Neal, Florida Keys News Bureau)
There they stayed until after his death, when his widow Mary opened the room. The items she found ranged from uncashed royalty checks, guns and hunting trophies to original manuscripts including sections of “To Have and Have Not.”
Since then Sloppy Joe’s, like a rare Cuban rum, has gained richness and flavor while its essence is basically unchanged. In 1981, it was the birthplace of Key West’s Hemingway Days celebration and look-alike contest that honor its most famous patron.
Today, visitors and Hemingway aficionados still flock to Sloppy Joe’s — including 125 to 150 Hemingway® Look-Alike Contest entrants, dubbed “the Papas” after Ernest’s nickname, who compete each year in the challenge that’s judged by former winners.
“Coming back to Sloppy Joe’s is a wonderful thing,” said Charlie Boice, who won the 2015 contest and returns each year as a judge. “For most people, it’s a destination on a cruise or a destination on vacation. But for the ‘Papas,’ this is home.”
May it remain so — for at least another 85 years.