The tradition of men in skirts goes back decades in Key West.


When it comes to cultural phenomena, there are two general truisms:

First, there is nothing new under the sun. (That is to say, nearly every idea we encounter on a daily basis, be it musical, cinematic or theatrical, is a rehashing or a retelling of something that came before.)

Second, cultural memory is notoriously short, which typically renders the average person less aware of (or at least less bored by) the existence of No. 1 above.

Given these two truths, one would be forgiven for thinking that drag is finally having its long-awaited cultural “moment.” Turn on the TV or scroll through your newsfeed today and drag seems to be everywhere. “RuPaul’s Drag Race” is about to enter its fourteenth season, “Pose” is changing lives and educating the masses on New York’s underground drag ball culture (and winnings tons of awards while doing it) and former boy bander Harry Styles even performed on “Saturday Night Live” wearing a dress.

But none of what we’re seeing today is even remotely new.

The Great Conch Republic Drag Race practically demands that participants don heels and skirts. COURTESY PHOTO

The Great Conch Republic Drag Race practically demands that participants don heels and skirts. COURTESY PHOTO

Consider the four decades from 1975 to the mid-aughts — Boy George (who was in fact a boy, but preferred not to look much like one) was a household name, RuPaul became a fixture on televisions across America, donning her sky-high wigs on “Hollywood Squares,” the ever-subversive Dennis Rodman was wearing dresses on a regular basis, “Hedwig and the Angry Inch” had exploded on the Off-Broadway scene and movies like “The Rocky Horror Picture Show,” “The Adventures of Priscilla, Queen of the Desert” and “To Wong Foo, Thanks for Everything! Julie Newmar” were, if not exactly blockbusters, at least popular enough that audiences across the world were becoming acquainted with the image of a man in a dress and a full face of makeup.

But even further back, the phrase “drag queen” first appeared in print in 1941 in Gershon Alexander Legman’s study, “The Language of Homosexuality: An American Glossary.” There, it was defined as, “A professional female impersonator; the term being transferentially used of a male homosexual who frequently or almost invariably wears women’s clothing, often for purposes of homosexual contact.” But if we learned anything in high school, we know at the very least that men dressing as women has occurred for centuries, even farther back than Shakespearean England.

The music continued to blast as firefighters fought the 1995 blaze that consumed the Copa, a famed gay disco on Duval Street in Key West. COURTESY OF FLORIDA ARCHIVES

The music continued to blast as firefighters fought the 1995 blaze that consumed the Copa, a famed gay disco on Duval Street in Key West. COURTESY OF FLORIDA ARCHIVES

Down in Key West, it feels like drag has existed as long as anyone can remember, even back in the days when the island was populated with no one but shrimpers and sailors.

And today, the Aquanettes and 801 Girls and the female impersonators who perform under their male names, like Christopher Peterson and Randy Roberts, are institutions. Local celebrity drag queens like Sushi and Inga are as recognizable by name — and more recognizable by face — to most locals (and many tourists, too) than Jimmy Buffett, Mr. Margaritaville himself. The girls hustle on Duval Street before shows and headline local fundraisers and variety shows. During the pandemic, Sushi, aka Gary Marion, and her merry band of fellow costumers churned out hundreds, if not thousands, of masks to raise money for the 801 Girls while the cabaret was closed.

Female impersonator Christopher Peterson actually does his own vocals for his Eyecons show at LaTeDa. He does a dizzying array of impressions — Marilyn Monroe, Tina Turner, Liza Minnelli, Barbra Streisand and, seen here, Judy Garland.

Female impersonator Christopher Peterson actually does his own vocals for his Eyecons show at LaTeDa. He does a dizzying array of impressions — Marilyn Monroe, Tina Turner, Liza Minnelli, Barbra Streisand and, seen here, Judy Garland.

So how, exactly, did we get to this cultural moment, where seeing a man in a wig and a dress has become almost mundane in its normalcy? In Key West, we have decades of drag foundations and a number of pioneering performers to thank.

From the Copa to CNN

The allure of gay tourism in Key West started to climb in the 1970s, when a number of gay guesthouses, bars and restaurants opened their doors. Two bars in particular, the Monster and Delmonico’s, were among the first establishments to host drag performances, although the shows were not exactly the choreographed masterpieces we think of today.

Longtime Key West resident Rikki Fessler, who moved to the island in 1978, discovered the Monster when he performed in drag there as a member of the Royal Scagettes, a cross-dressing musical comedy troupe based in Coconut Grove. At the time, both the Monster and Delmonico’s frequently played host to traveling female impersonators.

“Back in the early ’70s, before I came down here, Delmonico’s, which was located approximately where Rick’s is right now, brought a show called ‘Broad Minded Men’ down,” said Fessler. “It starred Michael St. Laurent, Stacey Carlson and Emory Dubois, who was a former Ms. Gay Florida winner. Delmonico’s was the only fully recognized gay bar in the city at the time, although Captain Tony’s was tolerant enough to host a drag group called Lip Sync that featured Gordon Ross, Kim Lempesis, and Michael Reece.”

When the Monster opened in the late ’70s, Fessler scored a coveted job as a bartender — and drag performer. “When the Monster started up, the bartenders formed a group called the Monsterettes and we’d do a show every few months with the bartenders performing in drag,” Fessler said. “It was gay camp, intended to be funny.”

Small though Key West may be (and it was much smaller back in those days), the drag community was not content to let the Monsterettes have their drag moment without some competition. After the Monsterettes came about, the bartenders at LaTeDa formed their own group — the LaTeDettes — and Papillon, which was located in the Atlantic Shores (an infamous and long-closed gay hotel), hosted its own merry band of White Glove Girls.

“I directed a show called Underestimated Understudies that brought in parts of each of those troupes — the Monsterettes, LaTeDettes and White Glove Girls,” Fessler said. “And as the drag community grew, the Fairy Garden Room at the Monster and then the Copa, when it opened, started bringing down big names in the drag and not drag worlds, like Eartha Kitt and Dana Manchester.”

The 1978 formation of the Key West Business Guild, a chamber of commerce type organization, was created in large part to promote the island as a haven for gay tourists and in the mid-’80s, Duval Street’s Copa and Club Epoch was the place for the gay community to see and be seen. Key West’s own disco inferno featured many androgynous and drag entertainers from the disco days, like Grace Jones, Vicki Lawrence and Divine. The Copa hosted grand theme parties where the dance floor was always packed and there was always a line to get in. When the club burst into flames in 1995, the music reportedly still blared inside while the firefighters doused the blaze.

What we now call Aqua Nightclub was once called Diva’s, a dance bar that also featured drag shows back at the turn of the millennium. And when 801 opened in 1987, the now-famous Sushi was working across the street, cleaning Bourbon Street Pub after hours. Before long, Sushi was hosting “Drag Your Friends to Friday,” a Friday night drag bartending event at Bourbon Street that quickly became the busiest night of the week. On the suggestion of Jim Gilleran, co-owner of Bourbon Street at the time, bartending eventually turned into drag performance.

One drag night became two, and then owners Gilleran and Joe Schroeder bought 801, where the outrageously popular drag queen R.V. Beaumont was already doing drag shows. Sushi was appointed drag queen in charge, and the 801 Girls were officially born. Today, drag shows at 801 and Aqua run the gamut, from wholesome and lighthearted to raunchy and blush-inducing. The girls lip-sync tongue-in-cheekily to songs like Shania Twain’s “Man! I Feel Like a Woman” and Katy Perry’s “I Kissed a Girl.”

New Year’s Eve 1998 was the first time that beloved local drag queen Sushi dropped down to Duval Street in her now-famous red glitter high-heeled shoe. In 1999, the story goes, a local cameraman filmed the shoe drop and put it on the internet and The Associated Press and CNN picked it up. The following year, CNN included the shoe drop in its coverage of millennium celebrations around the world and Sushi has been a New Year’s Eve staple on CNN every year since — Key West’s very own drags to riches story.

Drag for charity

Because their personalities are so much larger than life and outrageous, it’s sometimes easy to forget that Key West’s resident drag queens and female impersonators are an integral part of the fabric of the island, citizens who are civically active and invested in giving back to and bolstering the community in which they live and work. Since 1982, during the height of the AIDS epidemic, drag queens and chromosomal queens have competed for the title of Queen Mother, a contest held the Monday after Mother’s Day each year and organized by legendary drag queen John “Ma” Evans. As in your typical pageant, contestants compete in categories including appearance, talent, pose, and originality. The pageant raises money for a constantly rotating list of charities in town, from Helpline to the Florida Keys SPCA.

In 1983, Bourbon Street Pub hosted the first Conch Republic Red Ribbon Bed Race, in which local bars and establishments organize teams to push decorated bed floats down Duval Street to raise money for A.H. Monroe. And in April 1998, three years after the Copa had succumbed to its fiery end, Joey Schroeder of Bourbon Street Pub devised the Great Conch Republic Drag Race to rally the local gay community around a new tradition.

The infamous drag race, held during Conch Republic Days, practically mandates stiletto heels, mini-skirts and hairspray. Men in drag, decked out in daringly short dresses, makeup, and teased tresses, race down a block of Duval Street in their highest platform heels as they tackle an obstacle course, made all the more treacherous by the nature of the footwear involved. These obstacles include running football drillstyle through tires, weaving overstuffed shopping carts between traffic cones in a driver’s test from hell and dodging an abandoned wig or two like they’re banana peels in Mario Kart.

This (Wo)man’s work

Without question, Key West’s Christopher Peterson is one of North America’s most talented (and hardest working) female impersonators. In his nearly nightly Eyecons show at LaTeDa, Peterson does a dizzying array of impressions — Marilyn Monroe, Tina Turner, Liza Minnelli and, of course, Barbra Streisand, can all make an appearance on stage on any given night. And unlike the drag shows at 801 and Aqua, where the girls typically lip-sync their numbers, every note in Peterson’s show is sung by the man himself.

Peterson started performing in drag in Halifax, Nova Scotia, when he was fresh out of high school. “My real career started when I moved to Vancouver in 1982,” he said. “In 1984, I won the first Mr. Alternative pageant at the Orpheum Theater, and then I was thrust into a whole different world of professional drag. In the ’80s, drag was all about female celebrity impersonation. At the time, you only really saw men like Milton Berle doing impressions of famous women on TV, but Divine had just come on the scene and she was the first breakthrough star who had created her own outrageous drag character.”

Peterson, a Canada native, was working in Toronto in late 1997 when friend connected him with Sal Rapisardi, who ran Diva’s in Key West. “An eight-week run at Diva’s turned into 12 weeks, which turned into 23 years,” he laughed. “By then, the Copa had burned to the ground and so Sal decided to open up a small dance club called Diva’s, where he wanted to host full drag shows. Vogue, Vanna Black and Diamonique were the house girls and I came in and did the early show.”

It didn’t take long for the Diva’s drag shows to join the list of not-tomiss nighttime entertainment in Key West. “The first few weeks almost nobody showed up and then the buzz got around,” Peterson said. “I remember one Thursday night I was in the dressing room and Blake, the DJ, came to the back and opened up the door and said, ‘There are 300 people sitting down on the dance floor waiting for you to go on.’ And from that point on, every night 300 people would sit on the dance floor and wait. And it was a mix of gay and straight — exactly the type of audiences we’re getting now. It was a great, great time to be in Key West doing drag.”

It was during his stint at Diva’s that Mark Barauck, who owned LaTeDa at the time, showed him the plans for The Crystal Room, LaTeDa’s upstairs cabaret theater, and Peterson signed on to be one of its star performers. And even today, 23 years after he first started, Peterson — and Marilyn, Tina, Liza, and Barbra — are still performing to soldout crowds.

Though Peterson may dress in drag, he doesn’t necessarily consider himself a drag queen — a holdover mentality from his early days performing as a woman.

“When I first started in the business, being a ‘drag queen’ was a dirty thing,” he said. “A drag queen was somebody who wore big hair and too much jewelry and loud outfits. The goal for those of us in the business was to try to become a female impersonator. One of the things I learned right away was that you could have a drag name, like Sara Lee or Iris or Emerald, but if you wanted to be a professional female impersonator you had to have a stage name. In other words, you want the emcee to say, ‘Ladies and gentlemen, Mr. Christopher Peterson.’ And then the curtain opens up and a beautiful, glam woman is standing there and the audience goes, ‘Wait, that’s a man?’ And that’s why I’m Christopher Peterson and not Samantha.”

But the world of female impersonation has certainly evolved since the ’70s and ’80s.

“Drag has had a slow creep into the cultural consciousness, but it’s almost like what I do now is kind of considered not just passé but pooh-poohed,” Peterson said. “People go see drag shows and they want the three blue wigs and the clown makeup — what we call ‘clowning drag.’ That’s the direction that drag has gone in and it’s made it so that anybody can do it. There’s a fun good thing about that, but there’s also a sad thing about that. Whether you’re 7 or 70, man or woman, anyone can do drag now. Not everyone is good at it, but everybody can do it.

Drag for a modern era

Because of Key West’s status as a mecca for gay tourism, the island’s drag queens have the unique opportunity to perform every night year-round for a varied audience — men, women, gay, straight, locals, tourists, and every variation in between. Drag shows serve as an accessible way through which any individual, regardless of gender or sexual identity, can participate in gay life. And by making the gay world more available to anyone who cares to partake of it, the meaning of drag shows transcends the merely performative nature and becomes a greater statement on acceptance and equality. You don’t need to be a gender studies scholar to appreciate the nuances of a show in which a man named Roger Hultman can so convincingly transform himself from a club kid to a Swedish bombshell named Inga and wow a gay couple from New York City as much as someone who lives a more conservative lifestyle.

Interviewed in a Key West newspaper for a story about drag queens in Key West in the early 2000s, Sushi said, “We’re not just lip-syncing up here, we’re changing lives by showing people what we’re all about.”

Because the shows are so entertaining, and because they’ve become synonymous with Key West, they attract viewers who otherwise wouldn’t be exposed to gay culture. And in so doing, as Christopher Peterson articulated, they’re perhaps accelerating that “slow creep into the cultural consciousness” to the point where we’re not just experiencing one drag “moment,” but a phenomenon that will endure in its current intensity until the distinction between drag entertainment and non-drag entertainment is as blurred as Maya Montana’s flawless contouring. ¦

2 responses to “WHAT A DRAG!”

  1. Lynda Adele Frechette says:

    Laura Richardson’s article was exceptional as Laura herself. The Drag Artists in Key West are pure magic who spread joy to all and take us on a unique journey when they perform. Laura’s article was right on.

  2. Linda Park says:

    What. No mention of the drag shows at Delmonico’s? No mention of The Monster? Shirley Bassey’s, “This is My Life” was a masterful way to end her show (sorry…I don’t recall her name). It was powerful! 💃 👄

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