Sloppy Joe's Bar Key West
  • Key West's famed Sloppy Joe's Bar has welcomed patrons -- including literary legend Ernest Hemingway -- at Duval and Greene streets for 80 years. (Photo by Rob O'Neal)


  • By: Carol Shaughnessy
  • May 3, 2017

When Ernest Hemingway lived and wrote in Key West throughout the 1930s, he spent much of his leisure time with friends at Sloppy Joe’s Bar. On May 5, 2017, the iconic Key West watering hole celebrates 80 years at its landmark home at the corner of Duval and Greene streets.

Hemignway Look-Alike

Once a hangout of Ernest Hemingway, Sloppy Joe’s is the site of the world-renowned look-alike contest commemorating the acclaimed author. (Photo by Andy Newman, Florida Keys News Bureau)

The story of how it got there — and its significance in Hemingway’s life — is as intriguing as the plot of one of the legendary author’s short stories. And while we’ve explored Sloppy Joe’s history before in Keys Voices, the momentous anniversary makes it well worth recounting again.

FYI, the bar itself is older than 80 years. It first opened its doors at a previous location, on the day Prohibition was repealed in 1933.

Key West being a bastion of 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. Even Hemingway slipped over to Russell’s on occasion to buy illicit bottles of Scotch, and the two struck up an enduring friendship.

Joe Russell was a charterboat captain, rumrunner, Hemingway’s boat pilot, and the author’s 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.”

Hemingway look-alike contest supporters

Supporters of look-alike contestants cheer for their favorites at Sloppy Joe’s. (Photo by Rob O’Neal, Florida Keys News Bureau)

(Hemingway, by the way, has been credited with suggesting that Joe Russell call his bar Sloppy Joe’s — a name adopted from a favorite bar in Havana.)

In its early days, Sloppy Joe’s was located on Greene Street, offering attractions that included gambling and pool tables in the rear. “Big” Skinner, a hearty black bartender who weighed about 300 pounds, served Sloppy’s customers for 20-some years.

Hemingway 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.

Sloppy Joe’s migrated down the street to its current location on May 5, 1937, after Joe Russell’s landlord raised his rent from three dollars a week to a whopping four. Luckily, the former Victoria Restaurant at the corner of Duval and Greene streets was vacant. Built in 1917, the Victoria incorporated beautiful Cuban tilework, ceiling fans, and jalousie doors. Joe Russell quietly bought it for $2,500.

Oddly enough, the bar never actually closed during the move. Customers just picked up their drinks and carried them, along with everything else in the place, over to the new location. Service resumed with barely a blink.

Sloppy Joe's New Year's Eve

Sloppy Joe’s remains a center of Key West activities — like the annual New Year’s Eve celebration. (Photo by Carol Tedesco, Florida Keys News Bureau)

When Hemingway left Key West in 1939, he left a number of belongings stored in a house next to Sloppy Joe’s. After the house was sold, his things were moved into a back room at Sloppy’s. There they remained until after his death, when his widow Mary claimed them.

Since then Sloppy Joe’s, like a rare Cuban rum, has gained richness and flavor while essentially remaining unchanged. In 1981, it was the birthplace of Key West’s Hemingway Days celebration honoring the author who helped make it famous.

Today, visitors and Hemingway aficionados — including 125 to 150 Hemingway® Look-Alike Contest entrants every year — still flock to Sloppy Joe’s, drawn by the legend and hoping some measure of magic will rub off on them. And it usually does.

Happy 80th anniversary, Sloppy Joe’s. May patrons continue to enjoy cocktails and camaraderie within your welcoming walls … for at least another 80 years.