Stephen Winter’s ‘Jason and Shirley’ Cuts Deep Into a Black, Gay Classic of Essential American Cinema

Re-run for tonight’s Evening With Stephen Winter at MoMA

“It’s the only film that’s part of Essential Cinema that has a black gay man as its lead protagonist,” says director Stephen Winter about Oscar-winner Shirley Clarke’s seminal 1967 documentary Portrait of Jason, which serves as the basis for his latest film Jason and Shirley. As Winter’s first feature-length narrative work since 1997’s Chocolate Babies, his new movie takes Clarke’s now-iconic film and turns it inside out. Nearly half a century since Clarke turned the camera on Jason Holliday—a downtown legend, entertainer, and hustler with a larger-than-life personality—to deliver a radical and captivating documentary about persona, race, sexuality, and performance, Winter presents a fictionalized version of the chaotic 12 hours Holliday and Clarke spent together in her Chelsea Hotel apartment. 

In Jason and Shirley, Winter gives us a behind-the-scenes look at the making of Portrait of Jason, capturing everything from the exhausting push-pull of Clarke and Holliday’s director-subject power play to the provocation of Holliday’s astonishing emotional breakdown and the hidden memories of his painful past. Starring downtown theater veteran Jack Waters and Sarah Schulman (who also co-write the film), Jason and Shirley plays out with anxious fervor that builds slowly before coming apart at the seams before our eyes. 

This week, Winter’s film will have its world premiere at BAMcinemaFest. To honor the occasion we spoke with him to get a closer look at his personal connection to Portrait of Jason, how he and his collaborators crafted the film, and the cultural significance it holds today.

When did you first see Portrait of Jason and what was its immediate effect on you?

I first saw it when I was a kid, probably 21 years-old. It had a cataclysmic effect on me because it was the only film that’s part of Essential Cinema that has a black gay man as its lead protagonist—and it’s a devastating portrait. It’s hilarious, it is riveting, it’s brilliantly made, but it would appear, upon first watching, that Shirley is goading Jason into greater depths of emotional despair as the films grinds on. Then Jason himself is a black, gay prostitute; he hasn’t fulfilled his dreams of being a cabaret singer, and he seems to have a great deal of notoriety but not a lot of love in his life. He’s constantly chain-smoking, drinking, and referring to all kinds of drugs and the adventure of his past. It’s very intense. 

When you compare that to every other film ever made that has white gay people in it, it’s pretty rough. So it took me a long time to come back to it. Everybody who’s black and gay and into art goes through Portrait of Jason, and everyone interested in documentaries or essential cinema goes through it. Also, as the years went on, I noticed that although it’s on the top of the list for people who are interested in essential cinema, it’s not a film that’s embraced by gay people or black people—possibly because it has a whiff of exploitation, possibly because it’s so dark in its subject matter, or possibly because Jason is sort of a “bad subject” and not a positive role model. Although, you could look at the coded gay figures that appear in Hitchcock movies as murderers and such, they’re not great role models either, but they do get on the list of like, The 50 Gays Films You Have to Watch. But Portrait of Jason falls through the cracks. That’s also possibly because Shirley Clarke, although an iconoclast genius, as a female director in the 1950s was marginalized because of her gender. She always showed difficult subjects, mostly about black people, which also marginalized her. Even though she was a member of the Chelsea Hotel and was a legend, nobody writes books about her and nobody teaches classes about her. 

Where did the idea to invert the film come from, to show it from Jason’s perspective?

Fast forward years later, the idea of the film came up and I leapt on it. Taking that historical event and putting it in Jason’s perspective, I thought it could not only bring a full circle resolution to the questions and the pain that surrounds Portrait of Jason, but also reintroduce it to a whole new group of people—be it feminists, millennials, black people, or anyone who’s interested in issues of the human condition. Portrait of Jason should be up there with Paris is Burning and Fahrenheit 9/11, as one the most important documentaries. Jason Holliday, this historical figure who was a real person and lived in New York and was running around with Miles Davis and in the same circles and James Baldwin, he should be up there as one of the great creative figures and personalities of our time. He was living his life openly, brazenly, and with pride. After you’ve looked at Portrait of Jason multiple times, it’s amazing how much less of a victim and how much more of a human figure who’s a survivor he is—and that’s what’s so exciting about it.

How did you, Jack Waters, and Sarah Schulman begin assembling the film together?

It started with Jack Waters. Sarah, Jack and I have known each other for years, and they’re both geniuses. Sarah is an activist, journalist, and playwright; Jack is a legendary downtown performer and artist. The idea was bouncing around them that Jack should play Jason in something, and Sarah had the idea of: Why don’t you [Jack] play Jason, I play Shirley, and Stephen Winter write and direct it as a film? She called me on that just as I was going to start working on The Butler with Lee Daniels, where I was sort of his right-hand man in archival material. So when Sarah called me with this idea, I was so filled with the 1960s, but I was also exhausted. I said, “Let me think about it,” and went to sleep for a month. When I woke up, it was all there in my head: the perspective I wanted to take, the way I wanted it to look, what I wanted the ending to be. Everything that Jason and Shirley turned into was fully formed into my head. So it was a real organic creative process to create this emotional truth based on the historical fact.

Did your questions of exploitation in Portrait of Jason effect how you approached writing these characters and structuring the dynamic between them?

The only piece of research I did was looking up the making of Portrait of Jason, and the very first fact that flew out at me was that it was shot over a 12-hour marathon; it was just a nonstop shooting period. I was shocked because I had never asked myself that fundamental question: How long did they shoot? It’s ingeniously constructed because it’s all long takes looking at Jason and you hear Shirley Clarke’s voice on screen, and when the film rolls out it goes to black with audio, but then it comes back. So it gives you the illusion that it’s happening in real-time, that you’re watching, in real-time, a guy have a nervous breakdown—but it was actually twelve hours. So it was a 12-hour film with 10 hours cut, and that means the world is in there, and that means all the questions that I have are in there. So if it took her 12 hours to get that performance out of him, which a lot of people thought was Jason playing himself, then this is a story about two geniuses battling over supremacy of what is the truth. 

It was her wanting, him resisting, him wanting, her resisting. Now in real life, Shirley’s the director and she gets the final word. She gets to cut her film. In my film, it will be everything that was not in Shirley’s film, so it would be all those 10 hours now lost to history. I have my characters and what the goals are. It’s not about him versus her or her versus him, it’s that classic Rocky versus Apollo, that battle of the fittest. In real life, of course, Shirley cuts her own film, makes her a work of art, and she has the last word. But in the emotional life, it was Jason, from his perspective, who wins because he gets to be remembered, he gets to give a titanic performance unmatched in the history of film, and he gets to live on forever, which is an amazing thing.

He was also the first snap queen ever put on film. He snaps several times throughout the film, as we now do today. He’s the first person to talk about gay prostitution in such a frank way and talk about what like was like before Stonewall. If he’s not the first, he’s the first to give such a rigorous view from that world. If he hadn’t shown up that day, if he blew it off or Shirley hadn’t chosen him, imagine what would have been lost in history. So the fact that he did get into the room and he did give that performance and he got recorded, that is so beyond legend. It is shocking that up to now so few people have actually seen it.

How does Jason and Shirley, as well as Portrait of Jason, translate to cultural today? Why are these films vital now, and what do you want audiences to take away from the movie?

In terms of our national conversation around race, class, sexuality and gender—especially now that we’re at the end of the Obama era—the nation has done a lot of growing up, and it’s been a hard growing up for some. Sometimes it’s very empowering and sometimes it’s devastating as you look at the blood on the street. All people across the board are more alive to these things and more aware of these things than ever before. We’re not talking about skin color and sexuality or gender, we’re talking about the human right to be alive. This film was shot a year and a half after the Voting Rights Act of 1965 , and barely a hundred years after slavery ended. Think about that! Barely a hundred years. So this film asked, “Why are you alive, Jason Holliday?” Then my film is like, let’s go full circle on that question, and let’s all ask ourselves, why are we alive and why we sometimes feel apart from each other when we really should be together.

If there’s one thing I want to see on the cover of magazines in the next year, it’s black gay men, dressed as men, presenting themselves—not as something that’s unusual or is objectified or not understood, but just as people, as any other person. As a natural progression it’s gone from Neil Patrick Harris to Laverne Cox, and now it’s time for this. So often when you see black gay men in the media presenting themselves it’s around some issue. They’re depicted with some kind of grave expression on their face—that, or they’re being fabulous, which is fine, but not even a fraction of the whole. I’m just looking for humanity. I’m looking to make it no longer unusual. I met Laverne a couple of years ago when she was still an emerging actress, and she was like, “I’m here to be an actress, a trans woman who’s also an actress, and will play all types of roles.” I was like, “Well, hell yea.”  She also wanted to be the voice of the future to defend trans people, and she does. So black gay men next, without the qualification, just a person.

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