Director Stephen Winter Has Been Ahead of the Curve; The Curve Is Finally Catching Up

“Energy, more activity, more and more story, more character, more jokes, more to look at, more to feel,” is how filmmaker Stephen Winter described his sensibility in a recent conversation with Jezebel. The occasion for our chat was the Criterion Channel’s recent addition of Winter’s two features—1996’s Chocolate Babies and 2015’s Jason and Shirley—to its roster. The kind of institutional co-signing from a respected brand has often eluded Winter’s films, much to his frustration, as discussed below. And yet he has persisted. His decades in the business have included not only directing but also producing (notably on the 2003 documentary Tarnation, which played Sundance and Cannes), writing, and consulting.

Just getting his films seen has been a struggle, which is a shame because Chocolate Babies and Jason and Shirley are a blast. They share the aforementioned energy and manage to be brainy without being stuffy. The former was Winter’s NYU thesis film, shot in the mid-’90s when he was in his 20’s. He cast it mostly via a production of King Lear he caught at a ballroom house assembly. Conceived and filmed during the “plague years” of AIDS before the life-saving advent of protease inhibitors, it concerns a crew of “Black faggots with a political agenda” who refuse to be discarded for their serostatus, as society would have them. It is an incredible, uproarious time capsule of Black queer life in the mid-‘90s, with wide-ranging influences from his time in the activist group ACT UP to the antiwar protests of gay Black Panther Ortez Alderson to Hollywood heists of the ‘40s.

Nearly 20 years later, Winter released his second film, Jason and Shirley, which imagines the behind-the-scenes operation of Shirley Clarke’s beloved 1967 documentary Portrait of Jason, a filmic profile of performer, storyteller, and sex worker Jason Holliday. Writer Sarah Schulman plays Clarke, while Jack Waters disappears into the role of Holliday. A movie-long interrogation of power, it renders the subtextual text as a kind of ideological X-ray of Clarke’s source film.

Winter and I discussed his urgent, funny, and exquisitely paced work, as well as his triumphs in and frustrations with the movie industry. A condensed and edited transcript of our chat is below.

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JEZEBEL: Your Black queer identity is evident in your work, but I wonder how important you consider it to be to your art.

STEPHEN WINTER: What I think of myself as an artist, I think about the artists who inform all the things that I have drawn from, consciously or not. Terry Gilliam is up there. Ken Russell is up there. Repo Man by Alex Cox is up there. Punk rock stuff is up there. Film is so dominated by white men that you can’t help but use them as your artistic spirit, your guides.

Being Black and queer is part of what makes me fabulous, and in sense, legendary. I have that fire in me. It’s always been there. And part of it’s being Black and queer and American at the time that I was, but also part of it’s all the other souls of the soldiers who came before me. When I think about myself in a specific political sense, like when the Census comes, I put down Black because I wanted to know the Black person is living here. You are what the cops think you are. But when I’m with myself and my people, I’m a first-generation American, part Jewish, half Christian, Rastafari, Jamaican, Czechoslovakian. That is possibly why I really love Terry Gilliam.

How important is being acknowledged by an institution like Criterion to you? What does it mean to have your movies streaming on the platform?

Well, it means first and foremost, finally, people will be able to see my work. As a director, my work has never been embraced or accepted by the “Indiewood” community. As a producer, they do, but something about what I do as a director has always slipped through the institutional cracks. And, I always thought, unjustly. I could sit here and say my stuff is very good, but that’s not for me to say. What I can say very specifically is that it’s unlike any other movies. It has its own language, its own thing going on. And that’s usually something that the film business gathers around, and lifts up. I know it was institutionally inconceivable in the ’90s for Chocolate Babies to be raised up because it did not center a white protagonist. It had Black people and Asians. It wasn’t until Kyle Buchanan wrote about it in the New York Times last year—the headline said it all “This is the Criterion Collection. It includes 1,034 feature films… Only four directors are African American.” They called them to the carpet, and the company held itself accountable and made changes. And a year later, here we are.

One thing about being a Black person in America—and James Baldwin, of course, said it much better than I might say it now—is that you have to have a strong engagement with fantasy. You have to fantasize that something can be possible when it’s not. So I never let go of the fantasy that what I’ve been up to would be recognized. Lionization is a whole different thing, but not being able to get up to bat and being told to your face that Black people do not direct movies, much less a queer one and have that be the institutional norm for so many years, unquestioned. I don’t put that on any one thing. Like many Black people, it took 45 and a pandemic.

I’ve heard that the early to mid-’90s were a bleak time for AIDS. Media coverage had receded, but rates were still going up and so those disproportionately affected were on their own before the arrival of protease inhibitors. Did anger or frustration about that catalyze the creation of Chocolate Babies?

The film was conceived and shot in the time before protease inhibitors. The sense was that if you were HIV positive, you had a year to three to get your affairs in order and do what you have to do. The matter of factness of the way that people went about that life, I still have trouble wrapping my head around it. Even though I was there, it doesn’t necessarily still even feel that real, that people had to endure that. And then in ’96, when the film came out, protease inhibitors were announced, and that was great, but what people tend to forget is that the first few years of that were very touch and go. People suffered tremendously on those cocktails. It was like playing Whac-a-Mole with your illness: Your viral load goes down, but then this thing comes up. My HIV-positive friends were always having to renegotiate with the varietals of what they were doing and weigh the options. Being HIV positive was a life event that never ended even when the life got extended. So that’s part of why the characters act the way they do. They literally have nothing to lose.

It wasn’t until nearly 20 years later that you directed your second feature, 2015’s Jason and Shirley. Did you expect to launch a directing career after Chocolate Babies?

I certainly expected that I would be in the mix and do the do. And I was and I did. I had a great gang of peers and we would be in L.A., in New York. And we wrote our scripts, had meetings, attended symposiums, collaborated. But what I did find very consistently is that no combination of luck and hard work was going to work for me because there was no institutional apparatus that was prepared to receive me—even if I wrote the whitest, straightest movie, something that might be suitable for Julia Roberts circa 1999. I had white friends who would get development deals and such and they would tell me what folks said behind the scenes when they proposed, for instance, “Can we cast this supporting role as a Black actor?” [Those in power] would say, “If you put a Black actor in one of the leads your film, you are reducing its value.”

It was very clear that I wasn’t going to get the opportunities that my peers were going to get. I got none of that until I pivoted into producing because—and I think it’s very classic America and whiteness—folks liked to see me in a role where I was facilitating someone else’s vision. I was being a Morgan Freeman-slash-Whoopi Goldberg mentor character to white filmmakers. And this came to be a great success in 2004 when I produced the film Tarnation that was made on iMovie by the amazing Jonathan Caouette, who was a Texas native, self-taught filmmaker and had 20 years of archival material about his life growing up queer in Texas. He synthesized this movie, but he needed somebody to help him organize it, condense it, and get it out there. And that’s when his life and mine collided. And we joined forces and I gathered the materials and the team to help him facilitate his vision and use my industry knowhow and contacts and resources to do this impossible thing.

It was then shocking that in the two or three years that Tarnation was living in this world as a force to be reckoned with, the fact that I, Stephen Winter, a Black queer artist had produced the film was always erased. Sometimes I would get cropped out of photos before they were published. And you know, that’s part of the magic of movies. They weren’t supposed to know who the producer is. But it’s not about everyone knowing. It’s about 500 people or 1,000 who run the industry. And I couldn’t get meetings with them. And when I did, they didn’t take me seriously. They wanted to know more about what white people I know were doing.

I took a few years off and then my old buddy Lee Daniels was making Precious, an indie film and he brought me in to help. I worked on his films. I worked in other films, I worked TV, I worked on a pot farm. I did a lot of things. And then one day, Sarah Schulman, comrade in arms, came to me and said, “Stephen, I’ve got a great idea. Let’s make a movie about the behind-the-scenes of the Portrait of Jason shoot. I’ll play Shirley Clarke and our mutual friend Jack Waters, he’ll play Jason Holliday.” And I said, “Hell no. There’s no way I’m going into that room.” I had just finished helping Lee with The Butler, so I had been all deep into the 1960s. It was like, “I don’t even want to think about this anymore. I’m going to take a month off and sleep.” And I did. And then I woke up one morning and the whole film was in my head. It just came. I understood everything that we had to do. I understood who the characters are and what the story could be and how we would take the historical record and fictionalize it in a fantastic way. And I said, “Yeah, let’s do it.”

You know, we every aspect of the source material, we turned on its head. So while Portrait of Jason is known for its long takes and its rolling camera that stays straight, we’re going to be everywhere at once all over the place. We’re going to be in color, but it’s going to be subtle, like the medium itself is about to explode or come alive.

Was there a lot of research that went into recreating the famous documentary’s shoot, or is your film’s text based on interpretation and inference?

The research primarily was that Jack Waters, Sarah Schulman, and I have been living with the particular Jason text for most of our adult lives. And we had been reacting to it and stewing with it and understanding it for years. So we had that as a base knowledge. We also knew power struggle: between men and women, between Black people and white people, between Black people and Jewish people, between wealthy people and poor people, between artists and subjects. So that was our primary, our primary lens. And then everything else is in the text. Shirley Clarke is an awesome character because she makes herself so clear. And Holliday’s a historic figure. Something Jack and I understood is that what white people may see as a Black person just doing what comes naturally, we see all the hard work and the tears, we see the subterfuge. And looking at the film and the story from Jason Holliday’s point of view, that is what the story is. It’s about two titans fighting for domination.

You have so many ideas flowing through this film, you start screening it, and the people responsible for restoring and preserving Shirley Clarke’s work—Milestone Films—come out against it. (In a statement, the company accused Jason and Shirley of a “complete lack of research and their numerous factual errors and falsehoods have betrayed everyone who was involved in making Portrait of Jason.”) Looking back, what do you think about that? Do you resent their reaction?

This happened in 2015, the year before the rise of 45. A year before Moonlight. There was no way to position the conversation in a way that could be understood. The conversation was needed to be about Black filmmakers, Black artists having the opportunity and the freedom to express their stories from their point of view without being suppressed, and because the institutional apparatus of film was still guarded by an unquestioned, if unspoken, racial hierarchy where Black directors are not given the same opportunities as white directors, their complaint was able to stand as this. Only a few people read the complaint, but everyone who did was in charge of something. And so all the opportunities for the film went away and I had no way to initiate a conversation as to why this was happening. And when I did, actually there were baseline questions that you still had to get through in order to get into the conversation I really wanted to have. “What do you mean there are no Black directors? Isn’t there Spike Lee? What do you mean?” All the things that the big conversation of 2020 finally made very clear was not part of the national conversation in the art world in 2015. This is also before Atlanta by Donald Glover. This is before Get Out. This is before all the magnificent strides that have been made by Black creators who have become moguls. There are so many now that we can’t name them all. In 2015, we could still name them all, and they were mostly working in episodic television. So the frustration of that moment was I wasn’t able to say that I have no quarrel with Shirley Clarke. The response that they brought us was as if that was the purpose of the film, to take down Shirley Clarke. That is not that was not any of our intentions. And that is indeed not what we did. What we did is we created a fictional story out of historical record as hundreds of thousands of white filmmakers have done over the years with the big difference being that it was coming from Jason’s point of view, more or less.

You know, the fact that the work that I presented was ahead of the curve is a result of me and my comrades being on the right side of history. That’s a term that’s thrown around far too loosely, but it’s about whether or not your actions speak louder than your words. And when you act in a way that’s community-driven and it’s about elevating voices that are heard less than others, you’re always doing the right thing. I’m glad I lived long enough to see it come around.