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Stephen Winter Explains the Challenges of Being a Gay Black Filmmaker and His Controversial Decision to Reimagine a Classic Film

Stephen Winter Explains the Challenges of Being a Gay Black Filmmaker and His Controversial Decision to Reimagine a Classic Film

In 1966, legendary underground filmmaker Shirley Clarke invited the exuberant New York street hustler Jason Holliday to her Manhattan apartment and filmed him telling colorful stories from his life over the course of a 12-hour shoot. The resulting one-man odyssey, “Portrait of Jason,” finds the alternately hilarious and tragic figure proudly explaining his lifestyle while growing increasingly intoxicated. A radical, progressive look at an openly gay metropolitan figure both ahead of his time and trapped by it, “Portrait of Jason” was warmly received but only found broader acclaim decades later, when a restored version was released in 2013. 
Now, filmmaker Stephen Winter has revisited the project with “Jason and Shirley,” a freewheeling, comedic look at the rambunctious “Portrait of Jason” production that imagines the chaotic process through which Clarke coaxed a candid performance out of her real-life star. Littered with inside jokes about the New York experimental film scene of the sixties and the reckless abandon of filmmakers working far outside the commercial arena, the appeal of “Jason and Shirley” boils down to a simmering tension between its eponymous leads (played by Sarah Schulman and Jack Waters). The irreverent result suggests Christopher Guest by way of P. Adams Sitney — a playfully satiric look at the avant garde world through an intensely neurotic lens. 
Though “Jason and Shirley” has found supportive audiences at New York’s BAMCinemaFest and screens next at Outfest on Saturday, not everyone is so pleased. Milestone Films, the husband-and-wife team responsible for restoring “Portrait of Jason” as well as numerous other treasured Clarke films, posted a damning assault on the movie’s depiction of Clarke and various facets of the production on the company’s website. Calling the film “bad cinema and worse ethics,” Milestone’s Amy Heller complained that while “the filmmakers may call it an homage…their complete lack of research and their numerous factual errors and falsehoods have betrayed everyone who was involved in making ‘Portrait of Jason.'” 
In advance of the movie’s Outfest screening, Winter spoke to Indiewire about his inspiration for the project and his thoughts on Milestone’s criticism.
What has been your relationship to Shirley Clarke’s work over the years?
I remember one week in the ’90’s when James Lyons and I – James being the accomplished editor of Todd Haynes films and I was his young pal — went to see [Robert] Zemeckis’ “Contact,” which has a bravura sequence zooming from Earth far out of our galaxy with the historical noise of our TV and radio broadcasts trailing, until it gets to the silence of space – beautiful and terrifying.
Also that week, James and I watched “Portrait of Jason.” It was my second or third time seeing the film. After we compared the use of diegetic and non-diegetic sound in “Contact” and “Portrait,” and how wild Clarke was to interrupt her own film with her off-screen voice or edit Jason’s nonstop talk with silent surreal moments where cigarette smoke reverses, James was the first to explain to me that “Portrait of Jason” was shot in the Chelsea Hotel, and offer some background on Clarke’s relationship to her male peers. He explained the “evil” voice berating Jason at the end wasn’t a rogue camera crew but Carl Lee, a legendary actor as well as Shirley’s lover. James told me all he knew of Clarke and her concerns: “She was obsessed with ‘truth,’ even more obsessed with black men, and didn’t care what anybody thought of her.” He was very funny and very invested in getting me more interested in Clarke – and Jason Holliday. It worked.

Over the years, I always returned to her work and biography. But I still saw Clarke as just another reference point in the amazing yet maddeningly world of infinitely white film auteurs. Years later I remember thinking about James, now dead from HIV complications, while at another screening of “Portrait of Jason.” He would be pleased I was back at Clarke. 

What stood out to you about Jason Holliday when you first saw “Portrait of Jason”?
“Portrait of Jason” is the only film in essential cinema that stars a black gay man as its lead character. It’s not that there are a dozen films with black gay men and “Portrait” is the best. It’s not three or four films of different genres featuring gay black men and this is the doc. No. “Portrait” is all there is.
As a young gay biracial kid, a film student, a cinema lover and sensitive soul watching “Portrait of Jason” for the first time, I saw how unfair and terrifying my life in cinema was going to be. The intensifying isolation of “Portrait of Jason” cannot be overstated. I love movies. And this is the only vision it has to reflect me? What a sinister and predatory feeling, beginning and ending with Jason’s defeat and lack of agency from off-screen voices who seem to pummel him into submission. Jason has charm, nerve and a blaze of experience — but the film’s mise-en-scene is bleak, his prospects slim, and there’s no romance or hope. There’s only Shirley’s relentless camera, which makes Jason seem trapped in the frame in real-time.
Do you find that problematic?
Remember, during my first viewing of “Portrait of Jason” as a kid, I didn’t know from Shirley Clarke or understand the theoretical areas she was drawing from. All I could see was Jason, black and gay, sad and lonely – being yelled at by overseers just out of frame. Jason and the film ends with the subtle suggestion if the Jason Holliday in “Portrait” is the only Jason that exists, and if Jason Holliday is the only black gay man in the movies, he must be the only black gay man that has ever been. And he is a man defeated. Not a role model or “positive” image, or even an effectual tragic figure, just a tired clown, pinned under light. “Portrait of Jason” left me shaking with a new conviction: “I must never end up like Jason Holliday.” 
How has your relationship to the film changed?
“Portrait of Jason” has lived with me and many other people for decades, and since it remains the only essential cinema with a black gay man as its lead it was necessary for me to make my statement on it – in fact, the situation demands I do. “Portrait” is like the “Star Wars” of black gay man cinema — by way of [Pasolini’s] “Salo.” I use that comparison carefully, as “Salo” is a controversial vision that explores themes like abuse of power and sexuality, and although not strictly a horror film, contains a terror unique in film history. Black folks must freely critique representations of our image and provide images of our own.

There are some people who think Clarke was enabling Jason by letting him get increasingly more intoxicated over the course of the shoot. How do you feel about her methods and the ethics of the film itself?
My take after over 20 years of viewing is that Jason is not only complicit in his exploitation but ultimately the film’s primary engineer of narrative and characterization. Remember, Jason’s profession was hustling and part of the hustle is to take more for your service than what was originally offered, and hold your liquor longer than the mark. Shirley is the one who seems to give up and say, “End, end, end,” when she can’t stand to film anymore. But even though Jason is exhausted, blotto, sliding off the chair, you still get the sense he would do his Lauren Bacall impression or just about anything else if asked. He seems to consider this film more like a screen test in the “Hollywood” sense than a documentary. That’s the gloomy tragedy I find in “Portrait” — it’s like watching Jason endlessly audition for the role of himself – and still not get the part.   
Did you anticipate Milestone’s criticisms of your project?

I created “Jason and Shirley” to generate dialogue, so I welcome all viewpoints and ardent responses. The film was conceived, written, cast, shot, with editing well under way before “Portrait of Jason” was made widely available to see on home video or streaming platforms. In the decades between 1967 up until Milestone’s restoration, it was near impossible for an average person to view “Portrait” outside of academia. You had to be lucky enough to live near a revival house. So right now is an amazing moment for it to be widely available. The work Milestone put in to make that happen will always have my highest regard and gratitude. But I was aware that the relationship between fiction and reality in my film could be really intense to negotiate in a public forum. Jason Holliday doesn’t apologize for who he is. So by nature my declaration as a gay black artist to examine him in a film authored primarily by my assessments as a black and gay person, I knew there would always be someone out there who would see something completely different in my art than what I imagined. Such is the nature of art. My film is a work of fiction.
Did you do any research on the history of the production by reaching out to Milestone or others with background information?
It was never my intention to replicate that day, but rather to reimagine its historical and emotional significance from Jason’s point of view. So contacting people whom I don’t know wouldn’t help me get to the film I wanted to make. I wasn’t crafting a documentary, or biopic, or a remake. I needed to go deep into the archive of my own life to find the emotional truth of Jason. I had to get to the Jason within me so I could reveal the Jason within us all.

READ MORE: Ann Hornaday and David Sterritt Discuss Shirley Clarke’s Newly Restored ‘The Connection’

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