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Sloppy Joe's - A Key West Tradition

Updated on: Jan 25, 2024 9:11:51 PM

What is the first bar that comes to mind when you think Key West? Most likely Sloppy Joe’s,  the famous watering hole of Ernest Hemingway is a Key West tradition steeped in history.  Founded on the very day prohibition was repealed, December 5, 1933.  The bar actually went through a of couple name changes before Sloppy Joe’s was chosen with encouragement from the infamous Ernest Hemingway. logo-sloppyjoes2

Photo Credit: Sloppy Joe's Key West

Fearless rum runner/bootlegger & speakeasy operator Joe “Josey” Russell and his friend, customer and fishing companion Hemingway formed a special bond during the writer’s residency on the island. After the inevitable failure of “Operation Dry America” Russell found himself on the up & up as a genuine saloon keeper and business owner of a dump called the “Blind Pig” which cost him a whopping three dollars a week to lease the building. The pig was located around the corner where Capt. Tony’s Saloon still stands. (Fascinating history there too!) Built in 1852 the building served 2 important purposes. It was an ice house (very important due to the heat in Key West) and the city morgue (also very important due to the heat in Key West).

Thought to be haunted, the bar now houses the “hanging tree” where 16 pirates and a woman who took a knife to her husband and 2 children met their maker. Known as The Lady in Blue, (nicknamed for the color of her dress during the hideous killing spree and the color she turned during the ….).

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In 1898 a telegraph was housed in the same building. Famous for informing the world during the Spanish–American War that the battleship Maine was destroyed, when the news came from Havana to Key West.


Over the following decades it housed speakeasies, a bordello, a cigar factory and an early gay bar. The Navy forbade their men from patronizing the establishment which was ultimately forced to close and remain empty for quite some time until Anthony Tarracino opened its doors in 1958 as Captain Tony’s.

Not long after Joe Russell attained the Blind Pig in 1931, the ratty ramshackle establishment added a dance floor and changed its name to the "Silver Slipper" where in addition to gambling, gossip and ten cent shots patrons could now kick up their wobbly heels.

 An Old Havana bar and fish market where Joe “Josie” Russell and Hemingway spent considerable time while in Cuba was owned by another friend, Jose Garcia Rio. Joe’s Cuban bar was ridiculed as being  sloppy due to constantly melting ice that made a big mess of the floors….. Hence Havana’s aptly monikered “Sloppy Joe's”.  One thing led to another….. and one drink led to another…. and the Silver Slipper became the now famous Sloppy Joe’s at the urging of Hemingway!

Hemingway affectionately called his friend Josie Grunts, who he modeled the character Freddie in “To Have and Have Not”.

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Photo Credit: Sloppy Joe's Key West

On May 5th, 1937, after being told his rent would increase 33% from $3.00 a week to $4.00, he bought the building at 201 Duval Street, formerly known as “Victoria Restaurant” for $2,500.00 where Sloppy Joe’s has been since May 5, 1937! The move to the new location was actually pretty interesting with no disruption to operations, the bar never closed for a moment! On moving night, patrons simply picked up their drinks, carried the bar and furniture and walked across the street without missing a beat. Hemingway personally took the urinal from the wall saying something along the line of “He pissed enough of his money away in it”. Sloppy Joe’s is reputed to have accumulated a number of fixtures over its lifetime. Aside for Hemingway, back in the early years “Big Skinner”, a 300 pound giant of a man tended bar for more than two decades. The baseball bat he kept behind the bar, to this day hangs on the wall.  Back in the day there were pool tables and gambling in the back room.   

In 1933, artist Erik Smith painted a mural of Josie, Hemingway and Skinner that visitors can still see today.

There have been years of controversy pertaining to accurate history and credit for being Hemingway’s number one bar. When one considers a few certainties about the notorious word master, ( a. ) he was passionate about his libations, ( b. ) he was a true man’s man and ( c. ) he was loyal to the people and places he favored.

Sloppy Joe’s is a must stop for Key West visitors and also a favorite place for locals. Sloppy Joe’s is home to year round entertainment and events, food and libations 365 days a year! The menu which includes, of course, Sloppy Joe's is American and Cuban influenced with a variety sure to satisfy anyone.


Photo Credit: DeWolfe and Wood Collection in the Otto Hirzel scrapbook - Photo Florida Keys Public Library collection., Public Domain

Chances are pretty good you could spot a Papa Hemingway look-alike! They actually hold an annual contest you may want to schedule into your nest visit. 

Visit this link for the whole story, a virtual tour and lots more.

When you're ready to book your trip to the southern most island and make your pilgrimage to Sloppy Joe's, simply visit our booking page and get ready to have fun!

Hero Image Photo Credit: Historic Tours Key West

Topics: Walking Distance, Restaurants, Casual, Old-Town, Bar & Grill, American Cuisine

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