Florida Keys’ Most Iconic Bar Celebrates 85 Years this Week

Florida Keys. Sloppy Joe’s Bar. These two go hand in hand in the thoughts of millions when they think of our tropical paradise. Known in the hearts of many as their favorite corner bar, it has become one of the most easily recognizable and favorite tourist hotspots in the Keys, as well as many locals’ favorite hangout. The historic and iconic Sloppy Joe’s is celebrating 85 years this week. Though most enjoy an easy breezy time at the bar, Sloppy Joe’s actually has quite the history.

The origins of Sloppy Joe’s goes all the way back to Prohibition, in the early twentieth century, when the national government decided to experiment with legislating mandatory sobriety for Americans. When Prohibition made alcohol illegal, some citizens got creative and others decided to take a less literal approach to the law. One such citizen was none other than the original “Sloppy Joe,” Joe Russell, who operated an illegal speakeasy on Front Street. The underground saloon was a favorite of Ernest Hemingway, who would sneak over to purchase illicit bottles of scotch from Russell, and the two would go on to become good friends.

Sloppy Joe’s is currently located right in the heart of Key West, on the corner of the infamous Duval Street and Greene Street. It has not always had this location, however. Though this week, on May 5, the bar will celebrate its 85th birthday at its current location, it actually went through two different addresses before it finally came to be at its current spot back in 1937. When Prohibition ended, Russell leased a building in a new location on Greene Street for $3 per week and he became the lawful proprietor of a hole in the wall saloon called The Blind Pig. Shortly thereafter, Russell added a dancefloor to the saloon and renamed it The Silver Slipper, which grew in popularity for its comfortable easy vibe. It was the idea of famous patron, Ernest Hemingway, to eventually change the name once again - Sloppy Joe’s -  in honor of the proprietor and paying homage to the unique ambiance.

On May 5, 1937 Sloppy Joe’s moved across the street to its current address, into a building that Russell bought for $2,500. Legend has it that business was never disrupted during the move, as patrons simply grabbed their drinks (and chairs!) and walked across the street!

To this day, Sloppy Joe’s remains one of the most popular dives in all of the Florida Keys. Residents of Lower Keys real estate, especially Key West homes, love to pull up a stool and enjoy the vibe of this 85+ year old historic landmark!