feature image photo by David M. Benett / Contributor via Getty Images

“Oh hi there. I’m Zackary Drucker. I’d like to communicate to you some of my experiences being a real-life, full-time, continuous, self-actualized… person.”

Delve into Zackary Drucker’s extensive body of video art, performance art, and documentary, and you will find the shimmering soul of a singular artist. The pieces may vary in topic and presentation, but they all belong to the same ever-evolving voice.

Whether painted gold while unmummified or — quoted above — introducing a drag performance with the combined cadence of old Hollywood glamor and new Hollywood realtor, Zackary has long been interested in the parody of wealth. To be a woman is, after all, one of the most expensive things a person can do. Our society values a femininity only money can buy — especially if that femininity happens to be attached to a transsexual.

Zackary’s four-part HBO Max doc The Lady and the Dale focused on a trans entrepreneur’s pursuit of the American dream. Now she’s back with a new film, Queenmaker: The Making of an It Girl, that focuses on a very different trans woman and a very different American dream.

Queenmaker tells an Edith Wharton tale set in the other turn of the century. It’s the early aughts, and New York high society is the latest trend. By starting broad before narrowing in on its unlikely protagonist, Queenmaker is a dreamy, sticky, and thoughtful look at a culture of wealth and misogyny that was enviable until it wasn’t.

I talked to Zackary about finding the film in the edit, the ethical challenges of being a trans documentarian, and the female musicians who inspired her youth.

Drew: I want to start by talking about how you first became aware of Morgan and this story.

Zackary: This story came to me. I was finishing The Lady and the Dale in December of 2020 and MRC, the studio behind the film, reached out. They had heard the pitch and were looking for directors. And they came to me because of my personal connection to the material, having been in New York at the time as a young person. I had never heard of Morgan. But Morgan is going to be a big surprise to everyone. Certainly in the story itself, she kind of comes out of left field and steals the film.

Drew: It’s clear from some of the interviews that not all of your subjects knew where the film was going. When you’re approaching an interview how much do you let people in on the overall premise?

Zackary: Well, the premise was evolving. Truly. I knew that Morgan existed, I knew that she was the writer behind one the blogs, but the proportion of the film focusing on Morgan shifted. We had the backdrop: New York, the aughts, Tinsley, Olivia, Kelly Cutrone, the iconoclasts of that era. Morgan was just one part we were playing with.

The untold story behind the film is that we reached out to a lot of socialites and heiresses and other people and they just had no interest in talking to me. (Laughs) It was not an easy yes for a lot of people. They have more to lose than they have to gain putting their stories out there. And they were certainly skeptical that I was a woman named Zackary and that I was a trans person. If we had procured more of those interviews, the proportion of the film may have changed. But Morgan was always there and always game and open-hearted and willing to unpack what that time meant to her. As the door was slammed in my face over and over again by these other people, I was like helloooo this is the story, this is a microcosm of the American dream. Or the myth of the American dream.

Drew: So when you said you were hired because of your personal connection, did you mean your personal connection to this era in New York rather than a trans personal connection?

Zackary: It was probably both. As a filmmaker, it was clear we had an A story and a B story. And this is often the quandary as a storyteller. How do you structure? How do you weave? And ultimately, I think we wove the story really well. All the seeds that are planted in act one have something to do with a later piece in the story. We want the investment to pay off. And Tinsley and Morgan were the investment that paid off. It’s because they were both so willing to interrogate their own histories and go there with me. They could be seen in more complex ways than they had been, and have more control in the ways they’re represented.

Drew: I’m interested in the way Morgan’s transness is a reveal. Was that something that was found in the edit?

Zackary: Yes, it was. There were so many different versions. There were more versions of this film than any other project I’ve worked on. We continued to retool it over and over again. In radical ways. We tried every version.

Drew: What were the discussions around those versions?

Zackary: Do you start with the reveal? Or do you wait? Do you hold it? There was a real process of figuring that out. And we really sat with versions of the film for a long time until we realized that maybe we should try it this other way. It was a storied edit. (laughs) Of all the things I’ve worked on, this one was… storied. That’s the word for it. We were working on it for MRC, and then Hulu came in and there were more cooks in the kitchen. They had their own ideas about what would make the best story. And I was thrilled by that, because my goal is to reach different audiences every time. I want to get our stories out there. We all have to do this simultaneously for the rest of our lives, so I think about it practically. Hulu is a different audience. Hulu is an audience that watches reality television. So we were guided by the executives on how to reach that audience. How do you create a secret piece of trans activism in a story that’s extremely mainstream? (laughs)

Drew: It’s interesting, because it feels like a desire of “the suits” to have a trans reveal, but at the same time it doesn’t feel like any of the story’s integrity or Morgan’s humanity is sacrificed in service of that. It’s well-balanced. But I can definitely see an audience going into it and being totally surprised. As a trans person, I had an idea. I think the narration is a nice touch, because I heard a trans voice and had a guess where it was going to go.

Zackary: There’s a spectrum of legibility. And ultimately, I am always trying to speak to you, to my enabling audience, to the people who have the most advanced level of understanding. And, besides, the more specific you are, the more universal it becomes. I also want to create something that has enough layers in meaning that people can watch it again and get new things out of it.

Drew: Were there versions where you covered more of Morgan’s transition? Because that was something that was really interesting to me. You portray her life pre-transition and you portray her life now but you don’t get into the transition story.

Zackary: We did. We definitely did. There was a version that started with her transition. The version that we sat with the longest was beautiful steadicam footage of her checking into a doctor’s office to have a gender related surgery. It wasn’t about the surgery she was having, it was just her name and all the questions she was asked and her answering in really direct ways. It told you everything. It told you her name is Morgan Olivia Rose, that her legal name is James Kurisunkal, that she was a writer in New York. She tells this version of her story, and that was how we started. We said this is a trans person, this is who is at the center of the film, and then she drifts off into general anesthesia and it kind of brings you into the story. That was one version.

There’s a challenge as a storyteller. In the real world, if someone changes their name and their pronouns, you just refer to them always as that. But how do you tell something chronologically and still respect someone’s identity? There are nuances with Morgan’s story because many of the people who are referring to her are not in her life and don’t know that she’s trans. You have people still referring back and as a documentarian you’re not going to interject and correct them. It’s a very interesting position to be in as a trans creator with these stories that have not been told yet, figuring out how you do this in a way that doesn’t exploit or sensationalize somebody’s transness, but is still something everybody can understand.

Drew: Speaking of ethical dilemmas in documentary, I want to talk about the moment when you appear on camera to talk to Morgan. Obviously, as a filmmaker, a moment that raw is gold. But, after the fact, do you show a moment like that to Morgan and ask for explicit permission to include it? Or once the camera is rolling does everything feel like fair game?

Zackary: That’s something else that was in other versions of the film — conspiratorial conversations between Morgan and I about what she wanted to say and how she wanted to say it. There’s a version where we included some of our Zoom conversations where we’re collaborating. Because, for me, it’s always a collaboration with my subjects and my editor. There wasn’t anything on camera that we hadn’t already talked about.

That moment where I step in reveals how the toxicity of that misogynistic culture manifested internally for Morgan. You realize the self-talk that she learned from worshiping that culture had a deteriorating effect on herself. It’s very palpable in the women who I talked to. Even Tinsley would surprise me with things she would say, self-hating things. And I was just like, wow, that’s how you see yourself? It’s surprising sometimes. Like she’s the most beautiful woman with everything she ever wanted and still has a very pejorative way of seeing herself.

Drew: Do you watch reality TV? Is reality TV something you participate in as a viewer?

Zackary: No.

Drew: (laughs)

Zackary: (laughs) There are reality shows that I have watched and loved. I loved Small Town Security. But ultimately no. Because I’ve been a subject in reality shows, and I know how produced they are. There are writers on reality shows! They write the story and then you’re just a pawn in the story. Reality shows are very produced. They’re also listening to everything you say even when there’s not a camera on you and you’re just having an aside with somebody. They’re listening and taking notes and then a producer is reading it.

Drew: Do you think of it as like bad documentary filmmaking or do you see it as a whole separate genre?

Zackary: I have so much respect for the crews behind reality television. They work around the clock. They’re non-unionized labor, so there’s no limit to what they are asked to do. They are the hardest hustlers I have ever known in production. I want to say that. Production assistants, crews, anyone who works on a reality show is hardcore in a way that makes documentary look high-falutin. But it’s all a spectrum. Compared to scripted, documentary is very scrappy and very DIY. So I don’t want to reinforce the way I delineate between reality and doc. It’s just that one is usually much more manipulated and produced.

Drew: How do you feel your early experimental work influences your current documentary work?

Zackary: I approach all these works as an artist and a storyteller. I think as a young artist, I just never thought that I could exist in a mainstream area of culture. But I was like, okay, there are weirdos in the art world and that’s a place where I can get a job.

Drew: (laughs)

Zackary: You know?

Drew: Yeah.

Zackary: Then Transparent changed that. It was really the first show where somebody was like, let’s invite trans folks into this process as more than a consultant who comes on-set for a day, talks to an actor for a day, and then shows up for the premiere. That was the standard before. I’ve lived in LA for 18 years. There was no respect for us. Trans people were always associated with the underground world.

I think Queenmaker more than anything encapsulates my touch as an artist. Especially in the reenactments we do with Morgan. This is my third collaboration with Awesome + Modest, artist friends of mine. They always create a world that’s amazing but we really went ham on this. We were like let’s be weird, let’s make this look like early internet art from Paper Rad, this art collective out of Rhode Island in the aughts that were like so hot, or Assume Vivid Astrofocus, this other collective of artists that were creating interesting work. So all of that comes into play in creating a visual world.

I also never want to do the same thing twice. I think focusing the camera on me and my relationships as a young person was a really helpful way to construct an identity. And now I’ve expanded the view.

Drew: When you were a teenager, who were your models of femininity? Who did you look to the way Morgan looked to this New York elite?

Zackary: Truly, it was musicians. It was Ani DiFranco, Kathleen Hanna, Tori Amos. It was much more…

Drew: Lilith Fair.

Zackary: Oh yeah. I went to the first Lilith Fair. I was more counter-culture. By the time I moved to New York and was witnessing that culture of white, wealthy women, it was not my thing. I was not interested. I had a very critical understanding of class and equity. I was in college! I was steeped in theory.

Drew: (laughs)

Zackary: You know what I mean? I was like, what are these people participating in?

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