At the corner of Duval and Petronia streets, part of what’s affectionately known as Key West’s “pink triangle,” the 801 Bourbon Bar stays open until 4 a.m. Pink fluorescent lights spill out onto the street, where the crosswalks are painted in rainbow colors, and the sounds of ABBA can be heard from two blocks away.
Inside, the first-floor bar resembles dozens of others in Key West: alcohol, music, conversation, fun. But we weren’t here for that, and instead headed for the staircase in the corner.
“He is with me; we are doing an interview,” a grinning Jobie Jacomine told a bar employee while leading the way.
We headed upstairs, where he, Jobie, would become Puddin Taine, the well-known drag queen who has called Key West home for the past four years.


On the second floor, an intimately small stage awaited the evening’s performers and two bartenders set up a pink bar. But the black curtain and what lay beyond made this bar different. The curtain was heavier than I expected, and I hoped Jobie didn’t see me struggle to move past it. The room beyond, with its mirrors and makeup stations, could fit no more than three people, and my legs seemed to take up too much space, making me feel even more out of place.
The walls were obscured by more wigs and costumes than I knew existed — blonde, brown, red, pink; sequins, feathers and ruffles. Jobie sat me down at the mirror next to his, its corners covered by news clippings and photos (some I dared to look at only once). The counters, once black, were overcome with glitter.
This night would be different.
I found myself keeping my head down, unsure (or perhaps scared) of what I may see. Next to me, another drag queen joked, “Puddin’ is such a celebrity.” The subject of multiple articles and the recipient of several drag awards, she’s not just media savvy; she’s a media master and she wasted no time, first summarizing her routine on show nights:
5:45 p.m.: Cat nap.
6:30 p.m.: Wake up. Double espresso. Three cigarettes.
7:15 p.m.: Freshen up. “You have to be clean shaven for this job.”
7:45 p.m.: Get to the bar, always on time. Park in the semi-illegal spot in the alley.
7:50 p.m.: Apply Mehron makeup. Highlight first, then base, then powder…”Are you writing this down?” Contour with powder. “Blending is the most important step.”
(I had yet to ask a question.)
8 p.m.: Head down to the street below to welcome wandering crowds and promote the upcoming show.
Jobie had returned from New Orleans earlier that day, having spent the week performing and partying at Mardi Gras. Now, Puddin’ Taine would do the same back home in Key West.
Sitting on the sidewalk outside the bar, “Let’s hear it for the boy,” blasting in my ear, I witnessed the show before the show, promoted by the sales queen herself in a puffy black wig, bright green dress, a cigarette and club soda in hand.
Puddin Taine commands attention and each passing face bore a different emotion — fear, delight, excitement, disgust. People hugged her, swarmed her, talked and took selfies. Others looked away, even headed to the other side of the street (via the rainbow crosswalk). But all of them received the same unfaltering exuberance from Puddin. “Take a walk on the wild side,” she called, dancing to the music. She would continue advertising the night’s show until the place was full or it was time to head upstairs.

It’s showtime
Around 10:45 p.m., 15 minutes before showtime, I was told to sit at the bar for the performance. I chose a stool close to the back and farthest from the stage, hoping to observe without being noticed. Seats and tables surrounded the stage, which juts into the room like a short fashion runway. The crowd would fill in around it, with all but one couple sitting up close near the stage. They were in the back at the bar near me, also trying not to be noticed.
When the lights dimmed and the show started, my straight, 21-year-old eyes widened. This show was unlike anything I had ever seen or imagined. Five drag queens performed about 15 numbers. (I felt comfortable watching maybe three of them.) Reny Marie, 20, performed to Beyonce, then Michele, 67, paid tribute to Madonna, followed by Puddin dressed as the Liberty Bell.
It was mayhem for someone as out of their element as I, yet also somehow intoxicating. At one point, Puddin dragged an audience member on stage, ripping his shirt off before lifting and twirling him. (I missed the conclusion of that number due to the lack of clothes.) “He was heavier than I expected,” Puddin later recapped.
Working the crowd, she found the quiet couple in the corner whose eyes now filled with fear. “Honey, how y’all doing over there? Usually the straights are scared away by now,” she teased. They chuckled nervously, but she didn’t scare them off. Puddin made sure the crowd laughed with them, not at them.
Then her eyes met mine. When she told the audience she wanted them to meet a special guest, I grew concerned. When she beckoned me to the stage, I panicked. Standing on the edge of the stage, the attention had shifted. The eyes that had been on Puddin throughout the evening were now on me.
Proudly boasting that I was there to interview her, Puddin introduced me and told the crowd I was straight. It was one of the first things she had asked when we met, and I appreciated her willingness to make it known everywhere we went.
Standing on stage in a t-shirt, shorts and Crocs, I yearned for the obscurity of my seat in the back. I was out of my element, a naive newcomer, and yet Puddin and the queens had a way of distracting the uninitiated from their own discomfort. After the show, Puddin came over to check on me and asked my reaction.
“I saw things I never knew existed,” I said. it was a line she’d repeat to everyone we met for the rest of our time together.
Wait, what’s next?
We agreed to meet back up the next day at 11:45 a.m. — for the all-male, clothing-optional pool party she hosts every Saturday at the pool bar behind the Bourbon Street Pub Complex, diagonally across the street from where we were the night before. I went from being proud of myself for surviving night one to worrying frantically about day two, and my face apparently showed it.
“Only stay as long as you are comfortable,” she said.
When we met up the next day, Puddin was in the alley, smoking a cigarette and showing her friend pictures from Mardi Gras. “Don’t make it seem like I just smoke cigarettes all day,” she pleaded. i promised her I’d try.
Much more comfortable on our second encounter, I asked questions while she did her makeup. I learned about her drag family, her passion for stage play writing, and her dream of one day escaping to a farm. I learned about her weekday job at Blue Heaven restaurant, her love for her hometown of St. Bernard Parish in Louisiana, and the “cash-only Italian restaurant” job she had when she first came to the Keys (though she wouldn’t give many details). I heard about the difficulties of daytime drag in the heat, and some other, more personal, drag queen challenges. We sat and talked in a way that was more friendly conversation than formal interview. By the time we headed across the street to the pool party, I had filled eight pages of notes, and knew more about her than I did some of my friends.
To get to the pool, we went through another bar, this one darker than 801, and out a back door adorned with a sexually suggestive sticker. I took a deep breath and opened the door to whatever lay beyond.
Despite an entire childhood in Key West and a local’s familiarity with Duval Street, the existence of this pool and its surrounding garden bar area was news to me. There was a tiki bar, an upstairs sun deck and one men’s restroom. A Greek sculpture flanked the bathroom, and, much like many of the people around the pool, it didn’t hide much. A DJ was setting up under a tent in the corner.
Puddin again introduced me with the same “he’s straight” spiel, to which an older gentleman replied wryly, “That’s what they all say at first.”
Even as a writer, I was lost for words.
I then met 305 Mari. He was the DJ for that day and it was his second time ever working a queer event. As welcome as I’d felt by Puddin, the presence of another straight man was a welcome comfort. We talked for a bit as he set up, laughing about the uniqueness of our situation and the awkwardness of his first queer DJ gig. This time, he said, he’d brought a different playlist.
As the pool party progressed, it became increasingly difficult for me to look anywhere other than my notebook. Puddin had warned me that I would want to leave before everyone got too comfortable, and I started to understand why. A voice stopped me as I started to say my goodbyes, my eyes locked on the floor.
Conversations & connections
“You know, we are fun, cool gay people worth talking to as well,” said an older gentleman sitting next to a younger guy wearing large designer glasses. Despite their starkly different appearances, the two are happily married.
For the next 10 minutes, Jeff McQuary shared his story.
Upon coming out at age 15, he feared his military parents would send him to a “lunatic asylum” instead of college. He told me how his mom, up until his marriage, had relentlessly tried to set him up with women.
The marriage was set in motion by a former Republican state congressman in McQuary’s home state of Indiana. McQuary, a Democrat, had also worked in politics, and had celebrated when the powerful Republican state Rep. Sam Turpin was charged with bribery.
But McQuary had no idea, back in the mid-1990s that he and Turpin would become close friends 15 years later. And he certainly couldn’t have predicted that Turpin would help him meet his husband. The lesson, McQuary concluded, “Be careful who you are evil to.”
Like Puddin, conversation with the couple came easily. I was a tourist in their world and they were proud to be my tour guides. There was a sense of pride in everything they told me, and they clearly enjoyed showing off their lives to someone who had never seen anything like it. Puddin had told me she never viewed her job as unique or exotic, but there was always a sense that she knew it was chaos, and loved it. Despite her plans to one day escape it all, her passion for the lifestyle was obvious.
As I left through the bar and walked into the Duval Street sunshine, Puddin’s mic echoed from the pool bar and seeped onto the street out front. I chuckled at the idea of the outside world overhearing her and felt a tiny bit like an insider.
Before meeting Jobie/Puddin, I assumed we lived very different lives. It turns out, we occupied two different worlds. But I was welcomed into that world from the moment I entered and I experienced nothing but genuine hospitality (and some lighthearted ribbing). My two days in the queer world were intimidating, awkward and unpredictable, but unparalleled, eye-opening and unforgettable.
Guided by its celebrity ambassador, Puddin Taine, I was welcomed into the world of Key West drag. And while I never felt that I belonged, I was never made to feel that I didn’t.