Film Review: Jason and Shirley at BFI Flare

On Saturday, December 3, 1966, filmmaker Shirley Clarke sat down to interview local hustler and aspiring cabaret performer Jason Holliday about his life.   The interview, which took place in the living room of her apartment at the Chelsea Hotel in Manhattan, lasted an unimaginable twelve hours.   The following year that marathon interview was edited down to an hour and forty-five minutes and released as the acclaimed groundbreaker Portrait of Jason.

But what about those ten hours of unseen footage? What happened that night that we couldn’t see, didn’t hear and don’t know about? The 2015 film Jason and Shirley, which screened at this year’s BFI Flare LGBT Film Festival in London, ponders that question with a fictional reimagining of the evening.

Jason and Shirley

Jason and Shirley stars Jack Waters as Holliday and Sarah Schulman as Clarke – who were each tasked by writer, director and producer Stephen Winter with writing their own parts for the film.

What the three of them put together was an entirely possible (and maybe even highly probable) dramatization of the events of that evening with very little, if any, of the raw footage to draw upon. But given the fact that Holliday was gay, black and of very humble means while Clarke was straight, white and born into privilege on several levels, the sociopolitical dynamics at play during the filming of Portrait of Jason was a deep enough well to draw from in establishing the interrelationship between Holliday and Clarke at this time. But the film wisely avoids harping on those specific sociopolitical dynamics and instead — whether intentionally or otherwise — allows those to serve as an undercurrent to their story.

It is established early in the film that Jason was running late by at least two hours. Was it a power play on his part? Who’s to say? When he finally does arrive, it’s with such a flourish that you would think he was coming in to spontaneous applause from a live studio audience. And as Shirley repeatedly tried in vain to corral him into the actual interview – particularly with questions about his father, Jason requested more money for his participation, more alcohol and more “candy” (from a more mutedly fabulous dealer played by Bryan Webster). And then Jason did everything BUT answer her questions by regaling her and the crew with stories, observations and rather inappropriate comments about the super cute production assistant Nico (Eamon Fahey).

At the same time, you wonder if there is a reason behind the perceived lack of cooperation. Was Jason testing Shirley? Did he even trust Shirley? This was the late 1960s and tensions between the races were still smoldering — with flare-ups that continue to his very day.

With that in mind, is there a legitimate reason behind his mistrust? Beyond the mere aesthetics of their racial disparity, could Shirley really be trusted? She is a filmmaker after all (and one of the few women in the field at the time), so at the very least she just wants to get SOMETHING usable on film. And what exactly is a straight white woman looking to gain from an extended interview with a gay black hustler? Was she just exploiting an oppressed minority looking to establish a career as a performer and entertainer by giving him this opportunity to talk about himself? Or was she truly looking to hear about the gay black experience (at least this aspect of it) from the vantage point of a gay black man during that turbulent decade? Once again, who’s to say?

Eventually Shirley tires of Jason’s antics and calls in the cavalry in the form of the actor Carl Lee (played by Winter’s brother-in-law, Orran Farmer) to “break him” so that she can get some actual truth out of him.

But has she been getting it all this time without realizing it? What truth was she looking for? Tears? Hysterics? And is what she actually got from Jason really his truth? Did Jason show up with absolutely no intention of cooperating of giving Shirley what she wanted? And if that was the case, why agree to the interview at all?

The question of who is playing who – if anyone is playing anyone at all – is a fascinating aspect of Jason and Shirley. Waters and Schulman embody these two seemingly enigmatic figures very well — aided, I imagine, in no small part to Winters’ insistence that they write their own character’s parts. Together with Winters, they crafted a fascinating film about a fascinating moment in gay pre-Stonewall history.

Holliday and Clarke both died in the late 1990s, so there is a lot about the night of Saturday, December 3, 1966 in Clarke’s apartment that we will never know about – and for the sake of Jason and Shirley, this is a good thing as it allowed the film to live and breathe on its own without the constraints of having to be faithful to the events as they happened. And because we don’t know, Jason and Shirley has the benefit of reflecting this moment in time as opposed to having to re-enact it – which it does very well.

5 Stars

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All pictures reproduced courtesy of Stephen Winter

Terrence Moss

Terrence Moss

Film Critic
Terrence Moss is a Los Angeles-based blogger and writer who works at a media buying agency to pay the bills. He also contributes to the internationally-distributed Kraven Magazine, co-writes a web series called "Child of the 70s" and performs every week at Musical Mondays in West Hollywood. Terrence also watches a lot of old TV shows, gay indie flicks and other web series -- so he's quite single.
Terrence Moss


I wrote an episodic novel called I AM ERICK DAVIDSON. I also maintain a blog, operate a website, co-write a web series and have a column on GAY ESSENTIAL.
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