The Story Of… Sloppy Joe’s Bar in Key West

Exclusive Interview by Karen Beishuizen
Photos courtesy of Sloppy Joe’s and The Library of Congress by Arthur Rothstein

Sloppy Joe’s Bar in Key West, Florida opened on December 5, 1933, and changed location in 1937 to its current site at the corner of Duval and Greene. When Ernest Hemingway arrived in Key West, he tried to cash a check at the local bank, but they refused as they thought Hemingway looked like a bum with shorts and flipflops. At Sloppy Joe’s his check was cashed by the owner Joe Russell, and all of his future checks. A close friendship between the two men started and they made frequent trips in Joe’s cruiser to Cuba. The best on the menu is their signature Sloppy Rita and Sloppy Joe sandwich, so if you are in Key West visit Sloppy Joe’s and try it out!

KB: Tell me about how Sloppy Joe’s was founded?

Joe Russell was Sloppy Joe’s Key West original owner, born and raised in Key West. He was a charter boat captain and rum runner during prohibition. He started his legitimate saloon business at the end of Prohibition: December 5, 1933.

KB: I read that during the great depression in 1933 the bar disappeared from his original location and popped up at a different one?

In 1937 Joe Russell’s landlord tried to raise his rent from $3 a week to $4 a week and Joe said No. He quietly purchased the Victoria restaurant at the corner of Duval and Greene. So, in true Key West fashion, the bar never actually closed during its fast-paced migration. Customers simply picked up their drinks and carried them away along with every piece of furniture down the street. Service resumed with barely a blink and liquid refreshments were on the new house for the rest of the night.

KB: Tell me the story about how Ernest Hemingway discovered Sloppy Joe’s and became a regular.

When Hemingway first arrived in Key West and tried to cash a royalty check at the local bank on Front Street, the bank manager refused to cash the check. He did not think a man wearing shorts and flip flops would be in possession of the check. Hemingway went over to Russell’s place where Joe cashed that check, and all his future checks. Russell, a charter boat captain who ran a 32-foot cruiser called The Anita, eventually became Ernest Hemingway’s boat pilot, and was the author’s fishing companion for over twelve years. The two men became good friends and over the years they fished the Gulf Stream between Key West and Cuba. Hemingway called Russell “Josie Grunts” and used him as the model for Freddy, the owner of Freddy’s bar and captain of the Queen Conch, in the novel “To Have and Have Not” – and in many ways for the book’s protagonist Harry Morgan.

KB: Did the bar appear in movies or series? I read it was mentioned in Orson Welles Citizen Kane.

Sloppy Joe’s is mentioned in Orson Welles’s Citizen Kane. Scenes from Escape from Hell Island in 1963 and from A Murder of Crows in 1998 were filmed inside Sloppy Joe’s. The iconic Sloppy Joe’s Bar has been seen in many movies and commercials

KB: I read that Hemingway left behind memorabilia that is on display in the bar. What are the items?

When Hemingway left Key West for good, he left behind many of his personal possessions and papers which were moved into a back room at Sloppy Joe’s. The back room was call “the Hole” (a back room behind the long horseshoe-shaped bar) and this time capsule was untouched until 1962, a year after Hemingway’s death, when his fourth wife Mary opened the room and took possession of the items. Uncashed royalty checks, guns, hunting trophies, photographs, and original manuscripts, including sections of “To have and Have Not” were among the items found. Mary Hemingway allowed Sloppy Joe’s Bar’s owner, who at the time was Stan Smith, to keep some of the memorabilia for display in the bar.

The remaining items were left with Toby Bruce, a long-time friend of Hemingway. Bruce and his wife retained the items becoming the Hemingway collection which remained in Key West until 2021. Hemingway’s snow skis and fishing poles still remain at Sloppy Joe’s.

KB: What is the best food and drink on the menu?

Our signature Sloppy Rita and Sloppy Joe sandwich

KB: The exterior looks very colorful. Was it always like this?

Only two businesses have resided in this building. Built in 1917 the Victoria Restaurant 1917-1937 and Sloppy Joe’s Bar 1937-present. The historic building has remained the same. Canopies were put over front doors in the 40/50s and awning and neon lights in the 60s.

KB: Sloppy Joe’s has several locations? I read there is one in Havana. Is this one associated?

The location in Havana is the original Sloppy Joe’s. Hemingway and Russell often fished the waters between Key West and Havana. It was Hemingway who encouraged the Key West bar’s final name change to Sloppy Joe’s Bar. The name was adopted from Jose Garcia’s Havana club selling liquor and iced seafood. Because the floor was always wet with melted ice, his patrons taunted this Spanish Joe with running a “sloppy” place… and the name stuck. Somehow, it seemed to fit Joe Russell’s bar just as well. While our history is tied to the name Sloppy Joe’s, Key West is not affiliated with Havana.

KB: How did the bar survive the Covid pandemic? A lot of places went out of business.

Like all businesses the first several months of the pandemic were difficult but we are fortunate that travel and visitors has returned to Key West.

KB: Why should people visit Sloppy Joe’s?

Sloppy Joe’s has been at the corner of Duval and Greene since 1937 and throws the best party in town every day. We offer great food, generous drinks and live music 365 days a year! Sloppy Joe’s is A Key West Tradition.

Check out Sloppy Joe’s website: HERE
Find the bar on Facebook: HERE
Find the bar on Instagram: HERE

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