Becoming a Scoundrel in Key West
During the winter I was nineteen, I drove from Seattle to the Keys and learned to tend bar from a queen while I fell in love with three enchanted redheads
Dear Readers,
Key West is a place like no other. It’s where pirates mingle with drag queens, and the ghosts of writers like Hemingway drink cocktails with the phantoms of musicians like Jimmy Buffett.
Closer to Cuba than it is to Miami, it’s a place where beautiful, lost people hide out, playing in the sun until hurricanes make landfall. Where US Route 1 ends at the southernmost point, then it drops into the sea.
I got to live in Key West once, and it’s where I learned how to be a scoundrel. This story is about then…
When I was nineteen years old, I lived at the southernmost tip of the continental U.S., two blocks from Ernest Hemingway’s old house in Key West, Florida. My home was a one-bedroom shotgun bungalow with four other young bohemians. Two of them shared the bed, two shared the closet, and I was the lucky one who got the couch.
Despite my good fortune as the scalawag who landed on the couch each night, I didn’t sleep at our bungalow often, because I was lying in the beds of three redheaded enchantresses. A perfume paramour from Connecticut, a snake charmer from San Francisco, and a Georgia peach from, well, Georgia. And I was in love with each one.
But before I became involved with them, I learned to tend bar from a handsome, pepper-bearded older man named Daisy at a restaurant and dance club called Mangoes off Duval Street. It’s possible I was in love with him, too.
Daisy was a self-described old queen among the flock of fabulous queers who worked at Mangoes. I was the youngest of them all, and the only one to call himself straight. The staff all seemed to wait impatiently for me and my young, skinny self to change my sexual preference. At least to something more fluid.
But I was devoted to young women then, and each night, after my shift ended at midnight, I would rendezvous with the perfumist, the charmer, or the peach.
I had left Seattle the day after New Year’s Day, 1992, and drove down the coast in a two-door Corolla with a Wiccan priestess and a broken-hearted acrobat. The car’s transmission was going out, so I held the clutch down halfway with my foot for the one thousand miles to San Diego, where we stopped to party with a pack of surfers, and then we turned east.
After a week spent with methheads in Phoenix, we moved on to Kerrville, Texas, and the transmission stayed intact long enough to reach our destination. There, we helped destroy the last of a wine cellar from a bankrupt restaurant on the river. Afterward, the priestess and acrobat returned west, and I continued east with the restaurant’s former proprietor, Alaska Dan. His family lived on Big Pine Key halfway down the Florida Keys.
Soon after our arrival with Dan’s family, I discovered that his parents were apocalyptic, rapture-driven, born-again Christians who were hoarding large amounts of ant-infested food for the end times. So, I slipped out early one morning while everyone was still asleep and hitchhiked south to the end of the Keys.
Sporting long hair and a goatee like a rock ‘n’ roll pirate, carrying a heavy metal-frame backpack, and wearing wingtip shoes, I arrived where US Route 1 stops. The end of the road…in Key West.
Upon arrival, I knew immediately that my shoes had to go. I bought a pair of Huarache sandals for fifteen dollars on the waterfront and found a room at a hostel under the palm trees. There, I met a cadre of young bohemians from around the globe, and four of them became my bungalow mates.
Deadhead Micah was a clown who made balloon animals on the waterfront at sunset for tourists. British Bryan was teaching himself to play guitar while looking for work, so he didn’t have to return home. Tina from Phillie was bookish with fashionable glasses and searingly intelligent, and she cleaned rooms at a local motel. And Steve the poet was a cook at Jimmy Buffett’s Margaritaville.
The five of us moved into our shotgun near Hemingway’s ghost and the many descendants of Ernest’s cats who lived around his house. We couldn’t afford electricity, so we ran a long, brown extension cord to a neighbor’s house and stole power so that we could play our stereo and turn on our one single-bulb lamp. The shower ran only cold water, and music always played.
Each day, buses filled with tourists drove by on a historical tour. Before they rounded the corner to Hemingway’s, they would discover us and our friends hanging off the front porch, dangling like smoking monkeys. Tropical hoodlums, hippies, and alt-culture punks waving hello to the tourists became part of the tour.
I was running out of the measly amount of money I had saved from working as a barista at Pike Place Market in Seattle, so I had to get a job. One afternoon, I wandered down Key West’s main drag, Duval Street, peering into various establishments, until I saw Mangoes.
It was a beautiful outdoor restaurant, with tables under white tablecloths, a long, elegant wooden bar, and ceiling fans gently blowing. It was Casablanca with Leonard Cohen playing through the overhead speakers instead of Sam at the piano. Far from the frat and sorority parties down Duval toward Margaritaville. It was a magical place filled with Europeans and queer New Yorkers on holiday.
Sauntering in with my shirt open, I looked like a reject from Alice In Chains. Inside, the bar manager, Glenn, was cleaning the mirror behind the bottles. He was gruff, short, and flouncy.
“Who are you?” he asked with a groan as he wiped.
“Gentry. From Seattle,” I said. “I’m looking for work.”
“And…you want to do what?” he growled with a sparkle in his eyes.
“Bartend,” I said. I was cocky and under skilled.
“Well, we do need someone for the bar. Can you start tonight?”
“Absolutely.”
“Change your filthy clothes and be here at 3:00. You’ll be barbacking for Daisy. He’ll looove you.”
I procured a pair of khaki pants and a billowy white shirt that accentuated my pirate-ness, then I returned to the restaurant. Naive and spirited. I was entering a new world, and the eccentricity of the employees at Mangoes drew me in quickly.
There was The Contessa, a bearded and obesely overweight queen with a sparkling attitude and extraordinary wit who worked the back bar. In the kitchen, the head chef was Tony, a Sambucca-quaffing Italian who never cooked anything, and he was surrounded by a line of long-haired, tattooed cooks and dishwashers. Smoking a cigarette in a shadowy corner of the bar, there was a skinny, pockmarked Cuban who was always grinning and greasy; he was our restaurant manager, Raul.
Playing, serving, and twirling among all of the customers were a myriad group of extremely good-looking party boys. Chiseled and coiffed. All business at the restaurant, but afterward, drinks flowed, music pumped, dancing began, and ketamine, cocaine, and Molly were snorted and swallowed.
On my first night, standing behind the bar like the regal queen he was, Daisy was waiting for me. Early-50s, strikingly good looking, with short brown hair, needle blue eyes, and a cocky and feminine swing of the hips.
Daisy taught me to make everything. Sidecars, Grasshoppers, Brandy Alexanders, Negronis, Pina Coladas, chocolate liquor-based ice cream cocktails in tall glasses, and tropical rum rainbows in bowl-shaped stemware. While he instructed, I did all the work. He never picked up a bottle and never poured a thing. He just leaned against the bar, watching me lean over the beer cooler to pull out Amstel Lights and bottles of Chardonnay. After each customer paid, he also picked up every tip.
“You’ll see what you get from our tips after I see what you’ll do for me later,” Daisy said that first night.
At the end of my shift, I got to pour myself a stiff Tanqueray and tonic. Then, Daisy said, “Come over to my bungalow. It’s in the jungle. I’ll give you your money there.”
“Aaah…okay. But I do have friends to meet later,” I said.
“You can meet them afterward, honey. I’ll put on a Liz Taylor movie. You like her, I’m sure. And I have some outfits I want you to try. I don’t want them anymore, and I want to make sure they fit you.” Then, he nonchalantly winked. “It might get you a bigger cut of our tips.” As he said the last part, he made sure to punctuate tips.
At 1:00 am, we walked slowly to his bungalow in the jungle; Daisy pushing his bicycle and me walking beside him. The house was small and densely covered by palm trees.
Before we opened the front door, Daisy said, “I collect dolls. But you might not like them. They’re kitsch. Remember that.”
Inside, it was a small, cozy, and covered in collectibles and old dolls. Aunt Jemima, Little Black Sambo, and other teddy bears and dolls in black-face from the early 20th century sat on every surface and the few pieces of plush, vintage furniture.
Daisy had been sober for several years and offered me nothing alcoholic. To keep me there, he intended to ply me with hipster clothes from previous decades. To get them, I was asked to model. I went to the bathroom, stripped down, and changed, emerging to pose as Elizabeth Taylor yelled at Richard Burton in the background on the TV screen.
Finally, after much flirtation and many wardrobe changes, I was given a small percentage of our total tips, and I left the bungalow at 3:00 am. Though my evening take was small, I still had time to get to the bars, which were open until 4:00 am. I ran out into the sultry night carrying a small pile of clothes and a wallet filled with cash to spend on cocktails.
That pattern continued for the first several nights I worked with Daisy.
Each morning after just a few hours’ sleep and before my afternoon shift, I’d climb off my couch and walk several miles around a fenced-in military base to get to the locals’ beach. The ocean and the sand were my sanctuary. I’d drop my towel and plunge into the warm water, then slowly stroke backward as the small waves rocked me. Thinking of Seattle and music. No matter how far away I was from the Emerald City, I dreamed of making music there.
Then, I’d swim back to the beach and let myself dry off while I wrote lyrics and poetry. Scribbling strange and pretentious phrases as I lay on a towel on the soft sand. I focused on the words flowing off my pen onto the page until I fell asleep. Usually face down.
I’d wake in time to walk back, take a cold shower at the bungalow, put on my pirate’s bartending costume, and head back to Mangoes to tend bar, then gather my tips from Daisy in the jungle, and party with my friends until the sun had nearly risen.
It was a magically inebriated, carelessly lyrical, and hard work-filled time.
Then, Anathea, the perfumist, appeared during one of my late-night romps.
Anathea was twenty-two years of attitude, and she strutted through the bar I was in one night. Her long, muscular legs poured into high heels that seemed to make her nine feet tall. Ravishing red streaked her hair and bounced over the diabolical look in her eye. A succubus from the Northeast.
She walked directly up to me, parting my friends like a sinning Moses might a sinister sea, and said, “Hi. I’m Thea. I like you. You look like one of the Lost Boys.”
“The movie about vampires or Peter Pan’s friends?” I questioned.
“Both,” she said. “Buy me a drink.”
And I did.
That night, a tropical storm rolled in, and as the wind gusted and the rain fell, Thea took me by the hand to the end of the dock at the southernmost point. There, we drunkenly had mad sex like sea creatures as the waves banged the dock and covered us in water and foam.
After that, nights with Thea multiplied. I’d end up in her bungalow after work, where she would tell me I was too young for her. In the morning, after a rousing morning of sex, she would dress for work and head out to her Aromatics and Parfum Shop, which she owned.
Before she left, she’d say, “Leave the key under the conch shell outside.”
After only a week, she told me she loved me, then she put a cassette in her boombox and played Nirvana’s song Come As You Are. As the song played, Thea sang her own lyrics.
“Anatheeea,” was sung over Kurt Cobain singing, “Memoriiies, yeah.” And when the song ended, she said, “No matter what happens, you will never forget me.”
Daisy was both unimpressed and jealous of my new paramour, but Glenn had promoted me to a full bartender and moved me to the back bar in place of The Contessa, who was busy preparing for a drag show. So, I no longer needed to depend on my flirting in the jungle surrounded by racist dolls to get my full tips.
One day, I showed up to work and Daisy had dyed his hair red to match Thea’s. He had fallen for me as I had fallen for Thea, but both loves weren’t meant to happen.
After a full moon party, I ordered a round for Anathea and me at a rickety sailor’s bar we frequented, and then I went to the bathroom. When I returned, I discovered that she had stiffed me on the tab and left without saying a word.
The bartender looked at me and said, “That girl’s wild. She went to Miami Beach with a girlfriend to meet boys.”
Devastated, I left and wandered Duval Street in a drunken daze.
I was sliding down the street diagonally when I gazed into an open window. Standing by a black baby grand piano in a cafe, with a long waterfall of blazing red hair to her sumptuous bottom, wearing a short, flowery dress, was the snake charmer, Elyss.
She turned to see me standing there in the street. Piercing green eyes swallowed me. “You coming in?” she asked.
I smiled and weaved my way through the swinging wooden doors.
Inside, I played the piano, she brought me drinks, and then Elyss took me home to her room, which was a converted garden shed. She put me in a small boat in the canal behind her house, and after I was too wet to wear my clothes, she removed them and had her way with me for much of the night.
Elyss was a twenty-six-year-old hippie goddess. I called her the snake charmer because she owned two boa constrictors, her skin seemed to crawl like a snake’s, and her eyes entranced like one, too. Afraid of snakes since I was a child, Elyss and her serpents were a dangerous infusion of sex and death.
Like Thea just days before, Elyss and I became linked quickly, and I began to spend most nights with her, only stopping at my shared bungalow for a different pair of pants.
Elyss and I whirled through Key West and beyond. We took Molly and watched The Contessa perform opening night of her drag show at The Copa. We drove Elyss’ Dodge van to Bahia Honda to skinny dip in the daytime sun, where we filmed having sex by strangers on the beach. And we took a trip to tour the Salvador Dali museum in St. Petersburg, then saw Pearl Jam at a small club that night.
I had moved from one redhead to another quickly. Anathea to Elyss. Hungry, horny, and nineteen. It was all drugs and drink, lust and the beach. I was driven by desire and the need for more. For experience. For life to open up wide and swallow me whole. Living like Sonny Crockett in Miami Vice, all while behaving like a pirate gigolo at the edge of the world.
So, it strangely made sense that when I met the Georgia peach, I fell in love with her, too.
Heather was a character straight out of a Tennessee Williams production. Twenty-one years old with a shy-but-come-hither attitude and a coquettish Southern accent. All giddy and giggling, hips and curves, swerving through life in the Keys under a tousle of strawberry red curls. I was the bad boy. The scoundrel. And she liked that.
“You’re from Seattle? Like Nirvana?” she asked, several cocktails in at an Irish bar.
“I am. Well, I lived there. Before I came here,” I said.
“And you’re a musician, too, huh?”
“Yeah, I am.”
“If I find you a guitar, will you play me somethin’?”
“I’m a terrible guitar player. But I sing. And I’m not too bad on the piano.”
“If we can’t find a piano, then you can sing for me, baby.”
Heather and I found ourselves on the bathroom counter of her upstairs bungalow. The water was running in the shower, and we intended to get in it together. But we had become distracted by each other’s bodies, so we didn’t know the shower was overflowing and flooding the downstairs neighbor’s shop until we heard pounding on the front door.
It was that simple. Innocence mixed with lust. A third redhead (not counting Daisy) had entered my life. My sensuous chaos continued.
I continued to have affairs with both Heather and Elyss. When one worked, I played with the other. When I worked, I played with Daisy and all the pretty boys at Mangoes.
Moving from woman to woman and partying like a faux rock star, I began to not know what I was doing, but I was a young man, driven by want. The small sliver of land called Key West felt like it was closing in on me, and it was my fault that I felt the claustrophobia.
When Thea appeared at Mangoes one late Saturday afternoon just before Easter, she said she had gotten pregnant, had had an abortion, and wanted me to pay for it. We had never been exclusive, but it certainly could have been mine.
I didn’t give her any money. I was brash and naive, and I still held a grudge about her leaving me high and dry. And I had become a scoundrel.
That night, the Mangoes club had a dance party, and the DJ was pumping. Whirling from Thea’s news, I decided to get out of my head.
I danced with all the sweating boys and girls on the floor, flying high on the music. When my friend Don, an alt-rocker from Wisconsin, and I were offered Fantasy, I didn’t say no. Fantasy was a psychedelic mixture of LSD and Molly, and Don and I decided to take it at 3:00 am, just one hour before the club closed.
As the Fantasy began to elevate our senses, the lights came on, and all of us club goers were asked to go home. It was 4:00 am, and we were left to the night’s leftovers and the hum of the tropics with drugs dancing in our systems.
Don and I spilled out in the night and made our way to the two-story, tin-roofed bungalow where he was staying, and where I was sleeping with Heather.
We didn’t want to wake anyone up when we arrived, so we went out to the patio overlooking the street, hoping to relax in a hammock. But I was restless, and the whir of the drugs was increasing.
“Let’s get naked, man,” I said, buzzing wildly, the world opening and closing with tropical breath.
“Aaaw, no way, man. No way,” Don mumbled.
“I’m doing it. Then, I’m getting on the roof.”
I stripped naked and climbed onto the steeply slanted roof of the bungalow. It was silky and soft under my hands and feet, the metal warm to the touch. I climbed up as high as I could and lay my naked body across its warmth near the peak of the roof. Then I spread my arms wide open, inviting the world in.
Time had ceased to have measurement, and I stared out at the night above me. It was thick, dark, and molasses.
Don peered up at me from below, whispering, “Man, I can’t get up there. It’s too smooth. How’d you get up there?”
I laughed, arrogant, young, fearless. Then, I felt raindrops.
Moments later, the sky opened on both of us. A tropical storm had burst and was pouring down on my naked body. I was elated. It pounded on my skin and rained a blanket down on the roof. Don hid under an awning, and I laughed between the huge, heavy drops.
Tropical storms came quickly and left even faster. This one was gone in twenty minutes, and when the rain stopped, the clouds broke open. Streams of sunlight blazed through the clouds’ parting, burning down on my naked body. Day and its light had arrived, and church bells began to ring, echoing through the streets.
I realized that it was Easter morning, and I was naked on a wet, tin rooftop in Key West, lying in a crucifix pose aimed toward the street at sunrise.
My chemical-fueled mind was burning with esoteric questions. Who am I? Am I a sopping wet sinner? Crucified for the sainthood of all the party boys, all the redheaded enchantresses, and all the other scoundrels like me?
That’s when I realized the roof was too wet for me to get down. Sliding down was a bad option because it was too slick. Then people started emerging from their houses to go to Easter Sunday church services.
It turned out that the answers to my internal questions had nothing to do with being a soaked messiah. Oh, my god, I thought. I am a drug-addled ignoramus. I am a dumbass.
Don whispered loudly up to me, “Gentry! You gotta get down, man. There are people. People everywhere, man!”
“Oh, shit,” I hissed to myself. “Shiiiit.”
I got myself prepared to slide down the side of the roof, possibly breaking bones. It was very steep and very wet, so I did my best to get my feet ready to land. I wiggled until my momentum began and I rocketed down, too fast to have time to be concerned about where I would hit, and dropped onto the patio hard.
“Fuck! You all right?” Don asked.
“Yeah. Damn, man. We gotta get inside!”
We slipped through the patio door and into the living room, panting, soaked, high, swiveling on our own thoughts, gravity changing, and then I remembered I had to work the Easter brunch shift at Mangoes’ main bar at 10:00 am. That was only a few hours away.
Easter Sunday was a dark mirage among all the colorful clothing and smiling customers. Elyss and Heather appeared at the bar, each separately, happy to see me. I thought, they have to know about each other, and they probably did. At least, I tell myself that now.
The next day, I went to a travel agency and bought a one-way ticket to Seattle, but I didn’t tell anyone, except for Glenn.
He said with a sneer and a smile, “The season’s almost over, and I think it’s time. Work your last week of shifts. Then, go make music. And don’t grow up too fast.”
People learned about my departure shortly afterward, but I kept it a secret that I wasn’t returning.
There was an impromptu going-away party thrown the night before I left. Micah, Tina, Don, Bryan, and Heather were all there. We drank like a hurricane was coming, I received many drunken hugs and kisses, and music pumped into the night.
Steve the poet was not there. After we learned he plagiarized all his poetry and was addicted to ketamine, he stole Bryan’s guitar, drove west to save Los Angeles, and was later thrown in a mental institute.
Elyss was also not there. We got together before the party. A goodbye for just us. She said she’d see me when I got back, but I knew she knew I wasn’t returning.
Anathea never appeared again other than in gossip and rumor. I still wonder if the pregnancy was mine, and I think of her when I hear Come As You Are.
Daisy was sad to see me go, and I was sad to say goodbye. His hair was still red when I left. Seven years later, I learned that he succumbed to AIDS and died in his bungalow in the jungle.
Heather got me to the airport at 5:00 am on that last day of April, still half drunk on scotch. Her lips were the final lips I kissed in the Keys. Then, I stumbled out onto the tarmac and walked up the short stairway into the plane.
I landed in Seattle on the day of the Rodney King riots. Paradise displaced by revolution.
As I watched the city burn that night from Capitol Hill, I thought about gentle waves, the smell of coconut oil, and the enchanting curves of all those I loved, on the opposite side of the continent, where the road ended in Key West.
An early, two-part version of this story was published by The Memoirist in April 2022.
This is dedicated to Daisy. Thanks for teaching me how to make the rainbow in a rum punch, you handsome, old queen.
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I love the images that this story brings to mind. Makes me want to have a piña colada. ☀️
What a wild story filled with romance, travel, and some unscrupulous rogue behavior! I loved it! After reading that adventure, it's nice to know that your life is a bit calmer and that you have Whitney now. :)