General Horseplay

Posted: 03.20.2025 | Updated: 03.25.2025

America takes pride in being home to various people and places. Its a country where drinking traditions and terror melt into a treasure trove of spirited whimsy. General Horseplay, the Southernmost point of the United States, holds a rich history and a particularly odd brand of nightlife. It has charmed visitors and entertained them for generations, even those stopping by from beyond the grave. 

It is said that the party is so good in Key West that the dead even raise a glass. Drink down some spooky tales on a Key West Ghost Tour tonight!

Who Haunts General Horseplay In Key West?

General Horseplay stands head and shoulders above the rest of Key West by offering unique twist on nightlife. They have a proud and perhaps unhealthy obsession with actor Bill Murray. 

But, you may find it even stranger that Bill Murray is not the oddest recurring face here. General Horseplay is said to host a frequent patron who, unlike Bill Murray, is quite dead. Read on and step into a bar full of, acclaimed writers, odd urinals, and a ghost who just can’t quit. 

The History Of Key West

4 miles wide and 1 mile long. That’s it. Key West is, by anyone’s measurement, a tiny place. However, Key West’s location as the last stop in the United States before you take a dunk in the Gulf of Mexico means it has been an important destination for a lot longer than you may realize. 

This diminutive island for thousands of years was home to Calusa and Tequesta Native American tribes. It was discovered by Spanish explorer Ponce de Leon in 1513 as he attempted to reach Florida’s Gulf Coast. No doubt disappointed to have not found cocktails and live music, these enthusiastic Europeans persevered nonetheless.  

Spain however, assigned no real value to the island and the outcrop came under British control in 1763. 

The British generally frowned upon cocktails and live music, no doubt limiting their disappointment. But as was commonplace at the time, what was British, eventually, would be the property of the United States. 

For most of the 18th century, Key West was a haven for smugglers and buccaneers. Fishing in these generally unguarded waters was an attractive prospect for nearby Cuban and Bahamian fishermen. 

Then, in the 20th century, the Overseas Railway defied Mother Nature. Despite devastating hurricanes threatening to end the project it connected Key West with the American mainland in 1912. 

Despite being badly damaged by what is considered to be the worst hurricane ever to hit the United States on Labor Day in 1935, the railway was sold and used to create an automobile highway. 

This period transformed Key West from a poor and struggling economy to the wealthiest place per capita in the United States. It is noteworthy that people with money often enjoy cocktails and live music. 

From Hurricanes To Hemmingway

Another celebrated figure,, left an indelible mark on both history and the island. In the 1920s, renowned author James Joyced is said to have revelled in picking bar fights, before commanding, “Deal with him, Hemmigway! ” 

At which point his drinking buddy Ernest would step in and dismiss the aggressor with physical aplomb. 

In 1928, Ernest Hemmigway, the American literary of machismo and bravado,  and his wife Pauline chose to make Key West their home. 

The lure of sailing, big fish hunting, and the slew of energetic bars and clubs meant Hemmingway was as at home drinking in Sloppy Joes on Duval Street as he was in his study crafting loved works such as ‘Snows Of Kilimanjaro’ and ‘Islands In The Stream.’ 

Hemingway’s love of Cuban culture, general horseplay, and boating meant Key West was a launch point for regular trips to Havana and a source of inspiration. His feelings echoed those of former United States President Harry S. Truman, who once said of the place, “I’ve a notion to move the White House to Key West and just stay”.

It seems safe to say Hemmingway also loved Key West for its cocktails and live music. So much so, that when his preferred drinking hole, the notorious ‘Sloppy Joes’, owned by his close friend Joe Russell was renovated, Hemingway kept a piece of the bar. 

Hemingway removed an old urinal, still found today at the museum on the island, claiming, “I’ve pissed most of my money away in here so I can keep it!”. 

Controversially, local legend suggests another fate for the famed golden receptacle and an otherworldly patron who still likes to show it off. 

General Horseplay & The Ghost Who Spends A Penny

General Horseplay in Key West loves only one thing more than the free-flowing booze and the musicianship: Bill Murray. His picture is found all over the venue. They have a cocktail named after him (The Murricane) and one of his famous quotes gave the bar its name. 

When asked in an interview how he had injured his wrist, Bill Murray responded with his accustomed quick dry wit, “General horseplay”. A legend was born, it seems. Now if this seems like an entertaining fact you’ll love where the story goes next. 

Within the bar can be found an odd arrangement for one to relieve themselves: a double urinal. This old-fashioned and somewhat awkward tool for having two patrons spend a penny while facing each other is  best consigned to history. 

However, both customers and staff claim to regularly see the figure of an old man who died decades ago. This man would regularly and with great conviction tell all that the urinal inside General Horseplay is  the very same that Ernest Hemmingway saw fit to keep. 

This aged spirit is believed to be the ghost of Wilford ‘Red’ Williams. He was a local proprietor from the 1990s and Hemmingway’s long-time friend.

Old Red is said to be a regular sight by the bathroom entrance, where he nods and ushers onlookers inside. Old Red was loud and proud until his dying day that Hemingways Urinal, in fact, ended up inside the building that is now General Horseplay. 

Even in death, it seems, Red wants the world to know the truth. 

Haunted Key West

General Horseplay speaks volumes about the unique nature of Key West. While sipping your high-end cocktail and having involuntary thoughts about Bill Murray, you may very well be forced to stare at Ernest Hemmingway’s stolen toilet by the ghost of an old man long dead. 

It’s enough to drive you to cocktails and live music. 

Learn more about Key West’s haunted history and possibly Bill Murray on a Key West Ghost Tour. 

Follow us on Facebook, Instagram, and TikTok for haunted stories from around the nation, and keep reading our blog for the best-haunted history in America.

Sources:

• https://www.hauntedkeywest.com/news/haunted-bathrooms
• https://keysweekly.com/42/key-wests-general-horseplay-is-serious-about-live-music/
• https://www.keywestexpress.net/blog/ernest-hemingway-8-fun-facts-about-his-love-for-key-west
• https://fla-keys.com/keysvoices/hemingway-days-celebrates-legendary-writers-key-west-life/#:~:text=Ernest%20Hemingway%20lived%20in%20Key,are%20associated%20with%20his%20presence.