I learned to bartend from a handsome, pepper-bearded, and self-described “old queen” named Daisy in Key West, Florida when I was 19. It was at a restaurant called Mangoes off Duval Street, and I was the youngest and only straight bartender.
During that time, I lived two blocks from Hemingway’s old house in a one-bedroom shotgun gun house with four other young bohemians. I didn’t need to spend many nights there because I eventually had three magnificent redheaded girlfriends: a Perfume Shop Owner, a Snake Charmer, and a Georgia Peach. There at the southernmost tip of the U.S., I learned how to tend bar, be a lover, and a scoundrel.
I had driven down the coast from Seattle in a two-door Corolla with a Wiccan priestess and a broken-hearted circus acrobat. Then, in Kerrville, Texas, I continued east with Long Hair Dan. In Big Pine Key, Florida, I discovered that Dan’s parents were apocalyptic Born-Again Christians who were hoarding large amounts of spoiled food for the End Times, and I decided to hitchhike to Key West.
Sporting long hair and a goatee, carrying a heavy metal-frame backpack, and wearing wingtip shoes, I arrived and knew immediately that the shoes had to go. I bought a pair of huarache sandals for 15 dollars and found a room. I met a number of other travelers there and ended up renting a shotgun house with a few of them.
We could not afford electricity, so we ran a long extension cord from a neighbor’s house and pirated power so that we could play our stereo and a lamp. The shower ran only cold water and music always played. A bus filled with tourists drove by several times each day to point out our historical house en route to Hemingway’s around the corner. We would hang off the front porch, dangling our young selves like smoking tropical monkeys, and wave to the tourists passing by. Hoodlums, hippies, and alt-culture punks. It was marvelous.
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. I wandered down Duval Street one afternoon 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. Far from the frat and sorority parties down Duval toward Jimmy Buffett’s Margaritaville. A magical place filled with Europeans and gay New Yorkers on holiday.
Sauntering in with my shirt open, I must have looked like a reject from Pearl Jam. It was very early 1992 and the world was aflame with the sounds of Nirvana, Soundgarden, and Temple of the Dog. Inside, the bar manager, Glenn, was cleaning the mirror behind the bottles. He was gruff, short, flouncy, and liked me enough to hire me on the spot. I started that night as a barback for Daisy.
I procured a pair of khaki pants and a billowy white shirt, then returned to work. Young, naive, spirited, and anxious. I was entering a new world, and the diversity and eccentricity of the employees at Mangoes drew me in quickly.
There was The Contessa, a bearded and overweight queen with sparkling beauty and attitude, working the back bar. In the kitchen, the head chef was Tony, a Sambucca-quaffing Italian. And smoking a cigarette beside him was the skinny, seedy-looking restaurant manager, Raul, from Cuba.
Playing, serving, and twirling among all of us was a myriad group of extremely good-looking party boys. All business at the restaurant, but afterward, drinks flowed, music pumped, dancing began, and Special K, cocaine, and Ecstasy was snorted and swallowed.
Reigning behind the bar like the regale queen he was, Daisy stood waiting for me that first night. Late-40s, strikingly good looking, with brown hair, needle blue eyes, and a cocky and feminine swing of the hips. My being straight made me alluring but also irritating to him.
He taught me to make everything. Sidecars, Grasshoppers, Brandy Alexanders, Negronis, chocolate liquor-based ice cream delights, Pina Coladas, tropical rum rainbows, and coffee bean cocktails. 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 my ass bend 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 for a tip after I see what you’ll do for me later,” Daisy would say.
At the end of my shift, I got to pour myself a stiff gin and tonic. Then, he asked me, “Do you want to come over to my bungalow? It’s in the jungle. I can give you your tips there.”
“Um, ok. I have friends to meet though.”
“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 don’t want anymore. You can try them on to make sure they fit,” 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.
We walked slowly to his bungalow in the jungle, him 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 “black-faced” teddy bears and dolls from the early 20th century sat on every surface and on 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 clothes. Wonderful hipster clothes from previous decades, and to get them, I was asked to model. I went to the bathroom, stripped down, and changed, emerging to pose and dance as Elizabeth Taylor yelled at Richard Burton in the background on the TV screen.
Though there was much flirtation, Daisy was a gentleman. I was given 25% of our total tips and left his bungalow at 2 am. My evening’s take was small but I still had time to get to the bars, which were open until 4 am. I ran out into the sultry night carrying a small pile of clothes and a wallet full of tips to spend on cocktails.
That pattern continued nearly every night I worked with Daisy.
Within a week, tips in hand, I would meet Anathea, the Perfume Shop Owner, during one of my late-night romps.
Anathea was 22 years of attitude and strutted through the bar with 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 Connecticut. That night, we ended up drunkenly fucking wildly at the end of a dock at the southernmost point during a tropical storm. Waves banged the dock as we did the same.
Nights with her multiplied and I’d always end up in her bungalow where she would tell me I was too young for her. In the morning, after a rousing morning of sex, I’d stare up at the ceiling fan, wondering what time it was and how would I get my head to stop spinning before I needed to get to work.
After she told me she loved me, she said that I would never forget her name. Then she would sing it to me in place of the lyrics for Nirvana’s song Come As You Are.
“Anatheeeea,” would replace “Memoriiiies, yeah,” as the Nevermind album played on cassette in her home.
One night, she stiffed me on a tab and went to Miami with a pack of girlfriends. That night, pissed off and slightly drunk, I met Elyss, the Snake Charmer from San Francisco.
I was sliding down the street and gazed into an open window. She stood by a black baby grand piano in a cafe where she worked, with a long waterfall of blazing red hair to her ass, wearing a short, flowery dress. She turned to look at me standing there. Piercing green eyes swallowed me and brought me inside. A 26-year-old hippie goddess from the West Coast.
She took me home, put me in a small boat in the canal behind her house, and then fucked me roundly and completely all night, slithering like a reptile. I called her the Snake Charmer because she owned two boa constrictors and I had been afraid of snakes since I was a child. Her skin seemed to crawl like a snake’s and her eyes entranced like one, too.
She and I became linked, spending most nights together right away. We’d take Ecstasy and watch The Contessa sing karaoke at the Copa. We’d drive her Dodge van to Bahia Honda to skinny dip in the daytime sun, then be filmed having sex by strangers on the beach but never tell them we knew they were there.
I had moved from one redhead to another quickly. Anathea to Elyss. I make no excuse. Hungry, horny, and 19. It was all drugs, women, drinks, and dreaming of music. I allowed desire and the need for experience to control me.
That was when I was introduced to Heather, the Georgia Peach. She was a character straight from a Tennessee Williams play. 21 years old with a shy Southern accent, all giddy and giggling, hips and curves, swerving through life in the Keys under a tousle of strawberry hair. I was the bad boy. The scoundrel. And she liked that.
As Easter approached, I began an affair with her. One day, we flooded out the downstairs apartment below the bungalow she was staying in while having mad sex on the bathroom counter and leaving the shower running.
I really began to not know what I was doing, moving from woman to woman, sleeping behind their backs, and partying. My secrets were building and I knew my time was ending in Key West. I felt constricted, this small island closing in on me, and I knew it was my fault.
The day I went to the bar and saw that Daisy had dyed his hair red like Heather, Elyss, and Anathea, it became comical and Kafkaesque.
That night in late April, the club in the back of Mangoes had a dance party and the DJ was pumping House music. I was dancing with all the boys and girls, flying high on the music when my friend Don and I were offered Fantasy. A psychedelic mixture of LSD and Ecstasy. We decided to take it at 3 am, just an hour before the club closed.
As the combined drugs began to elevate our senses, the lights came on and all of us clubgoers were asked to go home. We were left to the deep night and the hum of the tropics with drugs dancing in our systems.
Don was an alt-rocker from Wisconsin with long razor sideburns and a mop of blond hair. He and I spilled out in the night and made our way to the 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 the 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, 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 come quickly and leave 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. Daylight was here and church bells began to ring all around. The deep resonance and high singing of the bells echoed through the streets.
It was Easter morning and I was naked on a wet, tin rooftop in Key West laying 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’s christ? Crucified for the sainthood of all the party boys, all the redheaded enchantresses, and all the 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 am a drug-addled ignoramus. I am a fucking dumbass.
Don whispered loudly up to me, “Gentry! You gotta get down, man. There’re people. People everywhere, man!”
“Oh, shit,” I hissed to myself. “Shiiiit.”
I got myself prepared to slide on my bare ass down the side of the roof and possibly break 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 rocketed down, too fast to have time to be concerned about where I would hit, and dropped onto the patio hard. Don, the true savior, helped to catch me and soften my fall.
“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 brunch shift at Mangoes main bar at 10 am.
I made it through that day, but it was a dark mirage. 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. Anathea never appeared in my life again other than in gossip and rumor.
Shortly after that Easter Sunday, Glenn told me the season was ending, so it was probably time for me to go back to Seattle. I booked a flight and left Key West behind within a few days of that conversation. Daisy was sad to see me go and I was sad to say goodbye. His hair was still red when I walked out on the tarmac to catch the plane.
Warm breezes, the smell of coconut, and the soft beds of tropical redheads were soon replaced by misty rain, the smell of fire, and the Seattle music scene. I landed the day of the Rodney King riots, paradise displaced by revolution.