Sloppy Joe’s and the Importance of Being Ernest
He might bear an uncanny resemblance to literary legend Ernest Hemingway, but he doesn’t do any writing — except, that is, writing checks and text messages.

David Douglas (right) gets a congratulatory smooch outside Sloppy Joe's from fellow "Papa" Tom Grizzard after winning the 2009 Look-Alike Contest. (Photo by Andy Newman/Florida Keys News Bureau)
So said David Douglas moments after winning the 2009 “Papa” Hemingway Look-Alike Contest at Sloppy Joe’s Bar, renowned as the author’s favorite Key West watering hole.
A mechanical contractor from Texas, Douglas was one of 140 contenders in the annual contest that attracts throngs of middle-aged men with white beards, stocky bodies, and an “ernest” desire to achieve “Papa-hood.”
He won the contest on his eighth attempt, after donning a cream-colored wool fisherman’s sweater despite Key West’s 90-degree heat — much like the sweater Hemingway wore in a famous 1957 photo by Yousuf Karsh.
Though he lacks literary aspirations, Douglas admitted several similarities to Hemingway beyond the physical. He’s passionate about all kinds of fishing and has been married three times. And he loves to go drinking with friends just as Ernest did when he lived in Key West throughout the 1930s. Much of the exuberant author’s drinking, of course, took place at Sloppy Joe’s.
The bar’s official beginning was December 5, 1933, the day Prohibition was repealed.

Sloppy Joe's is thronged with look-alike fans each year during the internationally renowned contest. (Photo by Andy Newman/Florida Keys News Bureau)
Key West being a bastion of free-thinkers even in the 30s, Prohibition was 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. In his company, Papa once caught an astonishing 54 marlin in 115 days. Hemingway called him “Josie Grunts” and used him as the model for a character in his classic novel “To Have and Have Not.”
In its early days, Sloppy Joe’s was located at 428 Greene St., where Captain Tony’s Saloon stands today, 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: John Dos Passos, Waldo Pierce, J.B. Sullivan, Hamilton Adams, Captain Eddie Saunders, Henry Strater. They wrangled, drank, and philosophized at the bar, never knowing they were building a legend.
Sloppy Joe’s migrated across 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 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 201 Duval St. where service resumed with barely a blink.

David Douglas, center, beams after winning the 2009 "Papa" Hemingway Look-Alike contest at Sloppy Joe's Bar. (Photo by Andy Newman, 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 “Papa” 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.
For David Douglas, 2009’s proud contest winner, it did.

















