Sloppy Joe’s Bar, Ernest Hemingway’s hangout in Key West.

Robert Morton
3 min readMay 23, 2021


Ernest Hemingway’s hangout- he actually wrote several novels while inside!

Sloppy Joe’s in Key West, the granddaddy of the Southernmost City’s drinking houses and a Duval Street heavyweight! As an author and fan of Ernest Hemingway, I walked into the place and took photos of the entire wall of hanging pictures and artifacts of his life. The manager and bartender enjoyed telling me about its historical bond to Hemingway.

It opened up in 1933, the day Prohibition was repealed, and went through several name changes and a sudden change of location before it became “Sloppy Joe’s”. It was a mainstay hangout for free thinkers, even in the thirties. In fact, Key West residents considered Prohibition as an amusing U.S. government exercise.

Then, along came a guy named Joe Russell who operated an illegal Speak Easy on Front Street. My mentor, Ernest Hemingway, made Key West his home back then and often slipped over to Russell’s to buy illicit bottles of Scotch. The two got along quite well and an enduring friendship began.

I pretended I was old “Papa” Hemingway himself and strolled into the bar, sat at a barstool and began plotting the MISSION OF VENGEANCE spy thriller. Rumor has it that “Papa” wrote several of his most famous novels while sitting inside Sloppy Joe’s, sipping his favorite drink (scotch). My spy thrillers are a different genre, probably won’t win the Pulitzer Prize for Fiction or sell millions like Hemingway’s “For Whom the Bell Tolls” or “The Snows of Kilimanjaro”, but I enjoyed plotting them out whilst sitting at the same bar stool where one of history’s greatest authors once did the same.

Although family-oriented now, it was once a rowdy, come-as-you-are saloon that was renamed the Silver Slipper upon the addition of a dance floor. Basically, it was a place of shabby discomfort, good friends and gambling, fifteen-cent whiskey, and ten-cent shots of gin.

But Hemingway had an influence on Russell and encouraged him to rename it “Sloppy Joe’s”. It was a club that sold liquor and iced seafood. Because the floor was always wet with melted ice, patrons taunted the owner, Jose (Joe) for running a sloppy place… “Sloppy Joe’s” they called it, and the name stuck.

I admired the wall inside Sloppy Joe’s and searched for a mural called “Hemingway and Friends”. There it was! I photographed it. Such history! In earlier days, “Big” Skinner, a huge bartender who tipped the scales at 300 pounds served Sloppy Joe’s customers for over two decades. Big Skinner was captured by Erik Smith, a WPA-era artist, along with Russell and Hemingway in the famous mural.

When you journey down to Key West, stop in at Sloppy Joe’s and enjoy the Hemingway remembrances inside. It was his favorite bar in Key West, a place where he drank many a night away during the 1930s. He plotted out and wrote about two-thirds of his published works there. Joe Russell, the owner, supplied him with copious amounts of scotch, in addition to 15-cent shots of whiskey.

Hmmm, I wonder if drinking scotch may improve my writing skills? The drinks are a bit more expensive. As I sat there, plotting out my MISSION OF VENGEANCE spy thriller, I sipped on their Rum Runner signature cocktail, also the official drink of Key West… get it, it’s good!

Lastly, enjoy the video: SLOPPY JOES’. It shows the Hemingway memorabilia on the wall, talented musicians playing on stage (The place rocks at 9pm on), the bartenders who are like family, and the long-curved mahogany bar.

Robert Morton is a member of the Association of Former Intelligence Officers (AFIO), enjoys writing about the U.S. Intelligence Community, and relishes traveling to the Florida Keys and Key West, the Bahamas and Caribbean. He combines both passions in his Corey Pearson- CIA Spymaster series. Check out his latest spy thriller: MISSION OF VENGEANCE.



Robert Morton

Spy thriller author, member of Association of Former Intelligence Officers, thrilling experiences await on my Author Site: