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“The Only Film in the Canon Which had a Black, Gay Man as its Lead”: Director Stephen Winter on Jason and Shirley

Jack Waters in Jason and Shirley

“Free love? That’s the only love I can afford!” Stephen Winter’s Jason and Shirley is no mere behind-the-scenes reenactment of the circumstances that would add up to Shirley Clarke’s seminal 1967 Portrait of Jason, but rather a full-bore interrogation of what Clarke’s documentary cost its participants during shooting. To those ends, the film’s rendition of gay hustler Jason Holliday (portrayed here by Jack Waters) is remarkable: it sketches out Jason’s dreams and nightmares in brazenly emotional flights of inward fancy, made all the more jarring by Waters’ unflinching, body-pressurized performance. As Clarke, writer Sarah Schulman gives off an uncanny with-it ness that’s as surprising as it is seamless to the film’s bleary, cigarette-stained milieu, shot on a handful of concurrent Super-VHS cameras. And as Carl Lee — Clarke’s collaborator and lover (as well as Jason’s) — Orran Farmer lends the shoot-within-a-film a Mephistophelean anxiety that’s all too common to any director-subject relationship.

Riveting even when it appears to dip into heightened states of vampiness, Winter’s film returns again and again to reframing Jason’s celluloid image, the impossible goal conjoining and contorting its characters’ muddled intents. Winter’s film owes as much to Clarke’s projected notion of verite (and its underpinning naiveties, none of which are portrayed as slam dunks against Schulman’s Clarke) as it does to the fluidity of ’80s video art. Whatever Jason and Shirley risks losing in veracity, it more than makes up for with its psychological ambition and sheer narrative force. While centering exclusively on a cluster of people trapped in a Chelsea Hotel room by their lights and cameras, the film moves nonetheless.

Filmmaker: To begin, can you tell me a little bit about your own personal relationship with Portrait of Jason?

Winter: I saw it in the ’90s when I was a kid. It was then, and even today still is, mostly known only to cinema people, documentary people. It wasn’t widely known or discussed in the gay or black community, even though the film seemed to intersect those things. I was just looking around for films about hustlers, Private Idaho kinda stuff — found the description in a library catalogue, popped it in, and it was a shocker. Being so stark, black and white, relentless, the camera grinding on as Jason talks and talks and drinks and smokes, and seems to be happening in real time. He seems to have a nervous breakdown, although the voices attacking him offscreen also seem to be goading him into it. But he also comes across as very sly, very much a survivor, so it just brings all these questions: what is truth, what is lies, and fundamentally, the question of “Why are you alive? Why are you — this black, middle-aged, destitute homosexual in 1966 at the Chelsea Hotel — alive to tell this tale?” I was shocked I had never heard of it, I never wanted to see it again, though of course I’ve watched it multiple times over the years.

I realized, as an aspiring filmmaker, that this was indeed the only film in the canon which had a black, gay man as its lead. And it’s just a devastating portrait: in the history of film, fiction and documentary, there’s all kinds of gay, lesbian and LGBTQ characters played by white people — never a character like this. Never anything as singularly devastating, albeit brilliant, as Portrait of Jason. So emotionally it opened up a lot of questions; I knew one day I’d have to investigate it.

Filmmaker: Your approach is somewhere between dramatization and fictionalization.

Winter: Oh, it’s totally fictionalized. 

Filmmaker: Right, but it’s drawn along the lines of what wasn’t included, what circumstances precipitated the marathon shoot of Portrait of Jason. What I mean is, your film centers exclusively on that process.

Winter: That was a starting point; the only piece of research I did was looking to see how the film was made and finding out it was a nonstop, 12-hour marathon shoot. Which was shocking to me, because I never had asked myself over these years, how long did they shoot? What was on the cutting room floor? Portrait of Jason is brilliantly made because it makes you feel like you’re witnessing something in real time, but really, there’s ten hours lost to history. That’s where I figured my film is. My film is about a sort of Ali-Frazier, Thrilla in Manila type situation — two equals, battling for supremacy of truth. The Jason that I was always looking for was the one who talked about civil rights, the one who was aggressive, stood up for himself, who was in cahoots with the creators of the portrait, who was as responsible for its content as Shirley was. What Shirley did to get that performance out of him — that’s where I realized I needed to be living.

Filmmaker: What’s interesting is, it’s a drama but it exists in this kind of twitchy, reactive present-tense, with no hindsight or exposition. It’s the shoot and nothing but the shoot. So: when you’re adding or subtracting a dramatic turning point, how do you decide to structure that? Do you go back to Clarke’s film again and again, or the opposite?

Winter: I had spent a year and change working with Lee Daniels on The Butler. He had put me in charge of researching and putting together all the archival material that would appear in the film — anything on the TV or radio, the White House shots, various other research. So I had spent a lot of time looking at everything, cataloguing everything for use in this film. I said, “I’m gonna go to sleep for a month now that we’re done with The Butler.” When I woke up, it was all there, all done in my head.

I knew it would start in the morning and go into the evening; I knew every step of the way, and part of it was just sort of the emotional truth, being a filmmaker myself, of knowing how things go on set whether you’re working with actors or doing documentary with real people. I didn’t watch Portrait of Jason again after the idea of this movie came up, I just drew from my memory of it. I knew the themes he was talking about, the stories he was telling, and just plucked the right out of my head, [as] a Christmas Carol-like visitation of ghosts. It all just sort of came from inspiration. I thought if I just kept going with the emotional truth it would all be there, so I plotted out the story and started writing. I put Sarah in charge of Shirley and Jack in charge of Jason, and we just set a shoot date and kept writing until the day-of.

Filmmaker: Has your estimation of Portrait, or of Clarke’s approach at large, been influenced by this process, whether for good or bad?

Winter: What’s wonderful and amazing about Shirley Clarke is, first of all, that she existed: an avant-garde woman filmmaker in the ’60s, who dealt with outsider subjects, specifically — almost exclusively — black men, at a time when no other filmmaker, avant-garde or otherwise, was focusing on them with such intensity. Carl Lee was her longtime lover and creative partner, and her outsider subjects and her controversial techniques — plus being a woman — kept her on the margins of film society, in a general sense and for decades to come. It’s arguable that only in the last few years has Shirley Clarke been reevaluated as as essential as she really needs to be, but there’s still no books written or detailed documentaries about her. One of the few people of her era, so important and so influential, and still relatively unknown. So I always had mad respect for her as a filmmaker, and how she did what she did. My personal feelings about it, in terms of Portrait of Jason, got quickly mitigated once I began to concede to the story, and realize it’s not about David vs. Goliath, or Jason vs. Goliath. Like I said: two great thinkers, two arguably messy people, trying to work out something for the truth. My job was to tell that historical event from Jason’s point of view, and to have every aspect of my film — the aesthetics, the storytelling quality, the emotional resonance, the way it looked — reflect what I thought would be inside of Jason’s mind, as Portrait of Jason is a reflection of Shirley’s mind. From there it was easier to go forward, because there’s really no bad guy, there’s no good guy, there’s…. just people. But the respect I had for Shirley has increased. Significantly.

Filmmaker: Given your prior considerations of the film within the civil rights era, do you feel this is a moment when bohemia failed the bigger picture? All the players you’re talking about were people angling to escape their prior identities, Shirley Clarke not the least among them.

Winter: It would appear so. She was born in a well-to-do family and was considered, in her day, by some people, at some times, as a dilettante sort of buying her way into the avant-garde, although history has borne that out differently. Being a woman herself, Sarah Schulman could speak to this a little more specifically — it was important to her to be identified with black men, because in society’s eyes, they were lesser than her as a woman. One thing that Sarah said to me very specifically when we first began was, “In 1966, it was a man’s world.” It was not like, “I’m a woman in a man’s world” — it just was a man’s world. And it was hard to think of it in those terms, how stark that is, but it’s true. So just for stepping out into the room and saying, “I’m a film director here,” it was of tremendous importance that she did it. 

Maybe that’s part of why she was attracted to black issues of the day. The civil rights movement, of course, was the most important thing going on in America outside of its participation in the Vietnam War. It is interesting to see how other makers of her day, Warhol for instance, seemed to be completely oblivious to it. Gene Roddenberry, in the same year Portrait of Jason was shot, understood that it needed to be a multiracial crew, and multi-ethnic. Lorne Michaels certainly figured it out by ‘75. But the Pop Art people? The Chelsea Hotel people? The Warhol people? Even though it was all around them, they let it go, I think to the historical detriment of what the Pop world turned into. Maybe Basquiat wouldn’t have had to die in the ’80s if people had been coming up in the ’70s, clearing the path for him.

It’s hard to be the first one, much easier to be second. Jason is the first snap-queen on film; that (snaps fingers) thing that all the queens do, to this day, he was the first to record it. Not the first to do it, but to record it. Shirley is the first person to have it recorded; you know, she was as much a member of the avant-garde art world as she was a member of the barfly world, the jazz world. She had her fingers in many pies, and traveled through a lot of different societies within New York, thank goodness. Otherwise, it would have gone unseen.

Filmmaker: Like you said, the film is clearly not allocating blame one way or the other. But things do get more complicated with the 11th hour appearance of Carl Lee. Can you talk a little bit about that “twist”, as it were?

Winter: When I first saw the film as a kid, there was no explanation as to what was happening – so in the “third act” of the film, other voices besides Shirley’s start to come at Jason. It’s African-American slang, and the voices are very aggressive; there’s some kind of terrible relationship going on between Jason and this voice. At first it sounds like maybe the crew has turned against him; for a decade, at least, I was laboring under that assumption. “Wow! Whatever went on that day – it was rough! Even the camera people are yelling at him!” But that wasn’t the case; the case was that that guy, Carl Lee, was a renowned figure in the hip world of the ’60s, and he was the son of Canada Lee, best known to film audiences as the black guy in Hitchcock’s Lifeboat. Carl, his son, was widely thought of in his day as being the next black breakout star, because he was so talented, so magnetic. He was also a drug user and a drug dealer, and very much committed to the outlaw life. If there had been an opportunity for a Sam Jackson-type star to emerge in the ’60s or ’70s, that would’ve been Carl Lee. But there wasn’t, so he’s in the Chelsea Hotel yelling at his friend Jason.

Knowing that, I say, OK, that’s how Shirley got to meet Jason, that’s how Jason is there, because there’s this other black man linking the two of them. For however it happened, Shirley brought Carl in at some point during that day to get some truth out of Jason that was not otherwise coming, or some kind of performance. The dramatization of that is what went into my third act. The basics of the historical act are true; in Portrait of Jason, Carl does discuss with Jason, aggressively, the reasons why you’re saying it was a love triangle. He makes it a question, but of course there’s a love triangle. Obviously, somebody like Jason Holliday would be friends with somebody like Carl Lee, and something would go down. Shirley’s opinion of that is neither here nor there — 

Filmmaker: Or at least, stricken from the record.

Winter: Well, y’know, it’s the Chelsea Hotel. This is where Allen Ginsburg and Brendan Behan were, all the white guys doing all the crazy things and all the crazy drugs, Burroughs and the gang. This was part and parcel of what was going on — Janis Joplin and the messy business of relationships. Lou Reed and Patti Smith would show up in the next few years. It’s part of what fuels that time. In Portrait of Jason it’s a very cruel situation, where it appears Carl is bringing Jason to the brink of hating him, but what’s the flipside of that? It’s that these two are brothers, and they love each other, and Carl is the only person in the room who really knows what Jason is going through. So our Carl is the suave, tender side of Carl Lee, and the stern paternal side as well. It’s not to negate anything in the historical record of Clarke’s film but, again, to find the emotional truth of what happened that day.

Filmmaker: A slightly more practical question: the lingo is of its period, and yet the actors sound like they’re talking to each other in 2015, not 1966. Let’s say this is aligned with your decision to shoot in S-VHS — how do you work away from such an iconic moment within documentary history? Even when we see through the viewfinder in your film, the aesthetic doesn’t look like Portrait of Jason.

Winter: Absolutely not. I love the ’60s, I love the slanginess of it, but the last thing I wanted to do was evoke the ’60s by having everybody walk in and start talking all kinds of jive. My experience of watching all that archive footage for The Butler was that people talked how they talked, and they were not self-consciously jive-y. When cameras were pointed at folks in the ’60s for news or whatever, there was no expectation that they were going to actually ever see it. People would look at the camera and just sort of be themselves, without today’s instinct of running back around and looking at the picture. It was just sort of, “Yeah, I’m gonna be myself, right here in this moment, and expect to never see the footage again,” and they probably didn’t. Less studied-ness to the way folks behaved: that’s what I tried to impart to the actors when we were writing stuff. So, once in a while I’d throw in some kind of hand-jive moment, but for the most part, people talked the way they talked. My only thing was, “I want you to be natural, in the sense you’re not living this moment, you’re acting it.” If you use the slang I wrote on the page, great. If you don’t, also great.

We don’t want to be poking folks in the head; the Super-VHS was gonna do that for us. I knew that my DPs would know what I wanted; I knew the VHS would give me the freedom to make the film with my third eye, rather than the studied way that it usually happens. VHS is kind of alive, you know? It’s unpredictable; it can warp, it can change. I thought, “Let’s be like Sun Ra, let’s play the space within the notes rather than the notes, and let the cameras dive and weave and get in there, in that way that’ll make us feel like a fly on the wall. The crazy colors, gorgeous grodiness of S-VHS will automatically put people in a different place.” You’ve gotta sit forward and look into the film, because it’s so unusual. It’s evoking something, even for folks who didn’t live in the VHS era. And not always the most pleasant thing; VHS brings to mind, not just an antiquated format but also something that may be kind of illicit.

Filmmaker: It’s more voyeuristic than the classical period piece style, right? 

Winter: Exactly. I wanted it to feel like maybe we were being voyeurs, we shouldn’t be there, in that situation. That’s what Jason was feeling, as the man they pointed their cameras at for twelve hours. I mean, can you imagine? Twelve hours. Of being under hot lights, and being asked to present yourself, over and over and over and over again? I wanted folks to be feeling that immediately. As well as, on Shirley’s side, the tension of being a woman and trying — beyond gender, being an artist and trying. She had made two features prior to this, low-budget ones, both about black people, and neither were as big a hit as they should have been. The Connection got tied up with some censorship issues; The Cool World wasn’t marketed right. So when she got here, there’s something  almost plaintive about it. Like, now she’s gonna make a film in her apartment with the bare minimum: camera, film, three or four people on crew, and this guy. And that’s the film that became an international hit. That adds something in hindsight, but in the moment of the story, she’s making another feature, she’s doing her job, she’s doing what she was here to do. And I wanted that intensity to come out; her goal, to make this film right.

Filmmaker: I think I spotted a few anachronisms or hyperreal moments— a piece of sound recording equipment, a skyscraper through the window, or maybe even a prop or something that looks, frankly, dubious. But my thought was, it doesn’t matter a whole lot to the experience of watching the film — the camera is constantly aborting and restarting its inquiry. Did you want audiences to watch Jason and Shirley self-consciously at all times?

Winter: I want you to get immersed in this experience. And emotionally, wherever you come out at the other end is where you come out. So, not to be too hifalutin, but (laughs) like Brecht, I didn’t want this to be a culinary experience but instead something you’d get plunged into, and you’d have to figure your way through it. You know it’s not a historical document, you know it’s a construction, there’s a hundred different ways that we made that clear in the first fifteen minutes. The set has an artificial look, but it feels lived-in; there’s easter eggs throughout it, actually. I felt that all that stuff would be to bring us, the story and the themes, into 2015. I wasn’t trying to do a Capote which plunges you into the ’60s and keeps you there, about Capote and his life experiences — it’s not really about today. Portrait of Jason? Everything going on in that film is going on today. I wanted that to be the complete, bold, italic, underlying message of everything that happens in Jason and Shirley. That’s why I shot it the way I did, that’s why I didn’t worry about the modern-day microphone. Of course, we could have gotten the prop, but it was more important that you don’t completely fall into the illusion that we’re creating.

Jason and Shirley plays tomorrow, June 18, at BAMcinemaFest at 7. Tickets and information here.

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