Despite the draw of a vacation spent entirely in the buff, there are plenty of good reasons to throw on a pair of shorts and hit the town in Key West.
The island paradise and must-visit gay travel destination boasts lively nightlife and topnotch restaurants, but look a little closer and find a thriving artistic community highlighted by one of the queer community’s greatest strengths: humor.
After a day soaking up the sunshine and a dinner date at any of Key West’s mouth-watering restaurants, nothing washes down dessert better than a show. Queer travelers looking for a gut-busting evening of entertainment have no shortage of options on the island, from live theater to drag shows and stand-up comedy.
True to the spirit of the island, the Key West sense of humor is eclectic and not afraid to get naughty. When that permissive atmosphere meets the talent of the community, magic happens nearly nightly.
We spoke with some of Key West’s favorite LGBTQ writers and performers about what makes the local scene so special and where to find a few laughs on your next visit.
You Better Believe
On a Thursday evening in Key West earlier this fall, a rowdy room is screaming along to a live performance of “Believe,” by Cher. There’s a married straight couple, traveling with siblings, a table packed with gay friends having a guys night out, two young nurses and more, all enthralled by what they’re witnessing. The diva’s perfect pucker, her long, raven hair, that unmistakable voice.
It’s not Cher on stage, of course, but it hardly matters.
Instead, the audience is en rapt by yet another performance from legendary showman, Randy Roberts. Alongside fellow celebrity impersonator Christopher Peterson, Roberts reigns over the cabaret theater of LaTeDa on Duval Street. He wows crowds with his Bette Midler, Mae West and, of course, Cher.
“Cher has become a rock concert,” he tells me one morning over a post-workout smoothie beside the Island House pool. “Cher brings them in, but Randy brings them back.”
He’s right. The makeup is incredible, he nails all the signature mannerisms and the actual live singing makes the chic cabaret theater feel like an arena.
But that’s not what makes it such a delightful evening.
Randy shines just as brightly when he drops the impersonations, whether that’s showing off his vocal chops outside the diva canon or in all the playful banter between numbers. As Bette or Cher or Randy, there’s not a moment where Roberts’ command of the stage isn’t on display. He’s particularly adept at needling a few of the straight audience members.
“My show is 80-90 percent straight most nights,” he said. “They bring their kids and their grandparents and everybody.”
It’s another perfect example of the island’s One Human Family ethos. Key West prides itself on its ability to invite visitors to “come as you are” and leave their inhibitions at home. It’s easy to let go when you’re in paradise, but there’s more to the island’s allure than climate.
Key West’s Duval Street Is Dense with Drag
“Drag sort of created what we see as modern Key West,” said Epiphany, a performer at Aqua on Duval Street. “People came down here in the ’70s and ’80s to escape — similar to Fire Island, they went to the farthest place they can go to be themselves.”
Unlike many cities, drag isn’t relegated to a gay neighborhood. (The entire island could be considered a gayborhood.) Instead, the main drag clubs are all prominently located smack on Duval Street, one of Key West’s leading tourist destinations for shopping, dining and entertainment.
Aqua is just a short walk from LaTeDa, where Randy performs. At Aqua, the gals lip sync to pop hits that delight the crowd. Between the two venues there’s also 801 Bourbon Bar, home to the 801 Girls led by the world-famous Sushi. Their proximity makes a “drag crawl” (or, let’s be honest, a drag stumble) easily achievable in an evening. Or, if you’re more of a morning person, there are drag brunches around the island.
“There are drag shows for all different audiences,” Epiphany said. “It’s amazing we can live on this island that’s 2-miles-by-4-miles and have that.”
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.
As for what makes the theater community so unique, Conrad says it all comes down to the people.
“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.”
A Key West Comedic Perspective
If anyone can speak to what makes Key West so rife for humor, it’s comedian Gwen Filosa.
“Kest West can be a goldmine of material,” she said. “It can be a really wacky place.”
Life on the island is just one source of inspiration for Filosa’s material, which she regularly performs at Comedy Key West. She gleefully cops to working blue (an industry term for more adult humor), and doesn’t shy away from material about her experience as a queer person.
“I feel really welcomed by the crowd,” she said. “It’s a very accepting place.”
That extends beyond sexuality. The same welcoming atmosphere that invites visitors to shed their inhibitions (and swimsuits) also helps unlock creative potential, generating an island full of artists.
“For a small town, Key West is like an art colony,” she said. “If you live here long enough, everyone seems to become a photographer.”
She’s kidding, of course. Not everyone becomes a photographer. They also become burlesque performers, chefs or any number of artistic pursuits — even comedians, like Filosa.
Before coming to Key West, pursuing stand-up was just a dream for the Indiana native. By linking up with the supportive community at the burgeoning Comedy Key West, Filosa went from open mics to steadily performing at the venue weekly. Now, her credits include performances at the Key West Theater, the San Carlos Institute and the Greenwich Village Comedy Club in New York City.
“Key West almost has a magical quality about opening doors,” she said. “You can be what you want to be here.”
That also includes just being an appreciative audience member. Comedy Key West and the local drag bars have lots of shows every week, while tickets for theater productions at the Red Barn Theater, the Waterfront Playhouse and Fringe Theater Key West are available online.