Drag, Comedy and Theater Keep Gay Travelers Laughing in Key West (Towelroad 11/19/21)

Key West’s History of Humor

Long before today’s queens were teetering on heels along Duval Street, Key West was a haven for all kinds of artists. Roberts is quick to rattle off writers that have lived on or have some connection to the island: Tennessee Williams, Ernest Hemingway, Truman Capote, Nancy Friday, Judy Bloom, the list goes on.

“Artists in Key West have always been important,” Roberts “I don’t know if it’s the location in the world, I don’t know about the spiritual aspect of it, but they’re drawn here.”

One such artist is writer Hy Conrad, best known as a writer and co-executive producer on Monk as well as work on White Collar and The Good Cop. Conrad was inspired to move to the island with his husband after visiting with comedy legend Steve Martin and being impressed with the theater community.

“The last thing we wanted was to find a place that felt very middle class and ordinary and people just gave up,” Conrad said. “A place where people just make a living and not trying to get the most out of their lives.”

Conrad certainly isn’t slowing down. Now, he’s getting ready for the opening of his latest play, “Quarantine for Two” at Key West’s Red Barn Theatre in February. The mystery-comedy is not only in Conrad’s wheelhouse, but he thinks it’s a great fit for the island’s sensibilities.

“Key West audiences are more discerning than the usual small-town audience, but they still like the popular things,” he said. “People like musicals, they like comedies.”

There’s more theater to be found at the Waterfront Playhouse, located in Mallory Square, as well as the Fringe Theater Key West, which changes locations for different productions. Both theaters have shows (musicals, comedies and more) announced for 2022.

“I think because it has a very community feel, there are a lot of smart people here,” Conrad said. “Rob Reiner once described Hollywood as ‘high school with money,’ and I’ve always thought Key West was like junior high with an open bar.”

As for what makes the theater community so unique, Conrad says it all comes down to the people.

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