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 Silverman, 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.