Over the past few years, Zackary Drucker has created an ever-growing body of documentary work about complicated trans women. In addition to co-directing The Stroll, her work on the docuseries The Lady and the Dale and her film Queenmaker: The Making of an It Girl challenged the kinds of trans women we usually see on screen. The series focused on a notorious con artist and the film focused on the writer of a high society gossip blog. In this work, perfect behavior is not a prerequisite for interest nor empathy.
Her latest, Enigma, tells the story of two very different trans icons: April Ashley and Amanda Lear. April was outed in 1961 and embraced her trans identity to much struggle throughout the rest of the 20th century. Meanwhile, Amanda always denied her transness allowing her a different kind of mainstream success. She still denies it to this day — even to Zackary in the film.
I spoke with Zackary about her idolization of Amanda, how she approached the ethical complexity of that interview, and the importance of embracing our ancestors even when they’re hesitant to embrace us back.
Drew: Can you talk about the genesis of this film? Did it start with April or Amanda or was it always both of them?
Zackary: I always start the story in 2001. I moved to New York City and my first friend was a fledgling trans woman who was obsessed with disco music and was a huge Amanda Lear fan. And at the time I guess I knew Kate Bornstein, but other than Kate I didn’t have anybody to look to in terms of a possibility model. So Amanda became my original archetype for being a woman. When I saw a photograph of her, I was amazed by how incredibly beautiful she was and I realized I could be a beautiful woman too. She inspired in some very deep, private part of me my own self-construction over many years. I’ve always been fascinated by her trajectory and her ability to invade. She’s somebody who had no tethers to her past, to her relationships, to a community. She’s completely self-made. And I think that’s a fascinating way of moving through the world.
Years later when Noah Levy, a producer on the film, brought the possibility to me to meet Amanda, I jumped at the chance. It was the opportunity of a lifetime. Never in my wildest dreams did I think that I would have the chance to meet her. And there are so few of these women out there at this point. The women in this film are the first generation of medicalized transsexuals. I think April was only the eighth person that Burou operated on. She was certainly the first person to have a surgery and then be outed, and I think her story explains so much about Amanda’s decision-making. It gives you all the cultural context you need to see how much entrapment the media could create for a person. And April is indomitable and so honest— well, she wasn’t honest about everything. (laughs)
Drew: (laughs)
Zackary: April definitely embellished. There were definitely stories where I was like did she really meet Albert Einstein? Nobody can really confirm. There are certain things like that, but by and large she was very honest and she paid the price. Amanda, on the other hand, created herself as a global superstar. And I thought they were emblematic of the two paths of trans life in the 20th century.
Drew: So when you went into your interview with Amanda, what was the context? How did you introduce yourself and what did she think the film was about?
Zackary: I mean, she was interested in telling her story in a documentary— in an HBO documentary. She agreed to the terms of the interview. She knew that everything was going to be on the table. Or, at least, that we would ask anything. She needed no media training or coaching. Her whole life has prepared her for this moment. It’s all part of her life as a celebrity. She’s been doing interviews like this throughout her life.
She didn’t necessarily clock that I was trans until I was there. And we didn’t talk about it until the last day of the interview. So that scene between us — the longest scene in the film — was after hours of interviewing her over three days. I just said, “You get to take a break. I’m going to tell you about me.” And I told her about being 18 years old and finding my way to her. And I told her what brought me to her. I explained my motivation and what she meant to me. The material is in the film, but not necessarily my backstory which is what I led in with.
Amanda is a Gemini. I have a Gemini moon. There’s a lot of identification happening. And that’s easier for me and I think more challenging for her in a way. But I didn’t anticipate how warm she would be when the camera cut. It could have gone either way. I was bracing myself— Of course, we were all bracing ourselves to get expunged from her home. The surprising thing was that she leaned in. And that’s the beauty of relational healing. Sometimes people surprise you and it’s cathartic. It’s beautiful. And I think there’s some kind of repair that happened in that exchange. For both of us.
These were not new questions for her. They were questions she’s been asked. But it was just who was asking and with what motivation.
Drew: I’ve noticed a bristling in some of the responses to the film from people who were not familiar with Amanda and who maybe are not familiar with your work in general. There’s this attitude: Just leave her alone. Don’t push. She wants to not be out, so don’t ask these questions.
Zackary: Don’t look at your hero! And don’t talk about her!
Drew: I have my own answer to these critiques, but I’m curious if you have a response to that way of thinking
Zackary: I don’t think it’s coming from trans women, I’ll say that.
Drew: Well…
Zackary: (laughs)
Drew: I have seen— Look, no offense to our community, but I do think trans audiences can sometimes be harsher on trans filmmakers and in general be quick to critique. But, I mean, did you think about this at all?
Zackary: Of course! All the time. Absolutely. I still think about it. And I was learning in the moment of interviewing her. It’s all happening on the job. And there’s vulnerability for both of us in that.
But when you author something, you never have any control over how it’s consumed or perceived, and it’s futile to try to exercise your will.
Drew: (laughs) Maybe I’m more interested in how you approached this issue separate from any responses to the film.
Zackary: I think it’s informed by my intergenerational friendships with other women like Amanda who were non-disclosing for much of their adult lives. Then at the end of their lives, they want to know that they have a legacy, and they do often approach the community again. I was curious if Amanda wanted that and I was curious if she knew that she had a legacy. Of course, she says, I don’t think about that. I don’t know. And it makes perfect sense, because she doesn’t have a youth culture adopting her and loving her. So I think it’s important whether they claim us or not to honor them. And this is my way of doing that.
I also think there are so few of these legends alive. I mean, they’re slipping through our fingertips. Two of the women who introduced me to Bambi and Dolly, one of them, Holly White, passed away this year and another is terminally ill. And it’s like how can we tell these stories while these people are still here?
If you’re a different filmmaker mining community for people who inspire you, there’s a much bigger pool to choose from. We don’t have a ton. (laughs) There are not a lot of these legends out there. And Amanda is probably the most accomplished person of our experience of the 20th century. So to say, no you can’t look at that person? This is my one life to tell these stories.
And I don’t know if you feel this way too, but I think people often have a paternalistic protection of trans women that’s actually infantilizing. I’ve noticed this argument isn’t coming from trans women — that I’ve heard! — but I have heard it from other people who say they want to protect trans women. And I’m like no you really don’t. (laughs) You really have never cared until right now.
Drew: Also Amanda is fine. No question from you is going to hurt her. As you said, she’s heard them all before.
I do wonder, as a filmmaker, how you find the balance between establishing a personal relationship and getting the footage that you want. You’re gaining trust and it’s not that the trust isn’t real, but you do have another goal.
Zackary: Absolutely. It’s a tremendous responsibility. And, ultimately, it’s consistent with yours which is to journalistic integrity and facts. You can only report facts. As a documentary filmmaker, we’re held to the same ethical standard. And trans people have always hit up against this. It’s always been a thing, right? Verifying who a person is often reveals that they didn’t go to that school under that name, etc. And in 2025 we’ve reached a place, thankfully, where there’s a trans person behind the camera who is making these decisions with more nuance and it’s not the kind of prurient, exploitative thing that it would be otherwise. Or that it often was historically.
I don’t know how much compassion Amanda has gotten from her audience and from her interviewers. So there was an element of healing in the exchange. I just learned so much from her in those moments.
Drew: Well, thank you for continuing to make work that’s complicated about trans women who are complicated.
Zackary: Yes! And I’m a complicated woman. Just like Amanda.
Enigma premieres tonight at 9pm on HBO and HBO Max.
