Bars & Saloons
Sloppy Joe's Bar
201 Duval St, Key West, FL
Sloppy Joe's Bar stands as an American literary landmark on the corner of Duval and Greene Streets, steeped in Ernest Hemingway's 12-year friendship with founder Joe Russell. The bar launched December 5, 1933, the day Prohibition ended, and relocated to its current corner location in 1937 during a legendary midnight move orchestrated by Russell and Key West patrons to avoid a lease expiration. Hemingway's connection to the bar runs deep: the author modeled a character in To Have and Have Not on Joe Russell, and the two were fishing buddies who spent countless hours on the Gulf Stream.
Today, Sloppy Joe's carries on its legacy with live entertainment every day of the year and hosts the annual Hemingway Days celebration each July, featuring the iconic Hemingway Look-Alike Contest. The bar's cultural significance extends beyond tourism—it remains a functioning neighborhood establishment where locals and visitors converge. Recognized on the National Register of Historic Places, the venue preserves the spirit of Key West's Depression-era resilience and its enduring connection to one of America's most celebrated writers.
Common Questions
What is the connection between Sloppy Joe's and Ernest Hemingway?
Hemingway was a regular patron and close friend of bar founder Joe Russell for 12 years. The author used Russell as a character model in his novel To Have and Have Not, and the two were fishing partners in the Gulf Stream.
When did Sloppy Joe's move to its current location?
The bar launched in 1933 when Prohibition ended and moved to its corner location at Duval and Greene Streets in May 1937, during a dramatic midnight relocation organized to save the business from lease expiration.
What historic recognition does Sloppy Joe's have?
The bar is listed on the National Register of Historic Places and hosts the annual Hemingway Days celebration and Hemingway Look-Alike Contest each July.