I haven't seen Portrait of Jason. I imagine as much will be true of many people who happen upon Jason and Shirley at festivals and other screenings. Those who have seen the film, which is said to be an entry in the canon of queer cinema, will perhaps glean more from Winter's film. Whether that "more" would cause celebration or consternation is difficult for me to say, though I must soldier on and look at what Winter presents.
Opening titles set the scene. Fresh off of an Oscar win, Clarke takes on some controversial subject matter: an intimate interview with a gay African-American man, Jason (Jack Waters). It's 1966, a time of change and charged political feeling in America, and the resulting film would present a frank, startling portrait of what it was to be a (double) minority during those electric years. Though the camera didn't roll all through the day, we're informed that audio recording never stopped, and thus, Winter imagines what was happening behind-the-scenes, giving us a sort of bottle episode of a film, almost a two-hander as the peripheral characters come and go and fade into the background.
Winter employs a found footage aesthetic: Jason and Shirley looks like a home video, the image almost framed within the Academy ratio. As far as the film tells us, there's no diegetic source for the images we see, no other person filming the proceedings. Instead, we are flies on the walls, seeing a slice of Vertov-esque "truth," though it is, of course, constructed and imagined. The film sometimes breaks from this visual presentation, even bursting from its aspect ratio in a particularly stunning scene. Though Clarke is calling the shots, not always heeded by her subject, we are more at Jason's mercy, going on psychedelic and kaleidoscopic flights of fancy, fantasy, and memory. We are mostly bounded by the four walls of the suffocating hotel room, with barely enough room for the three members of the crew to move around, but Jason frees us to see other spaces, and other aspects of his person.
The film, perhaps wisely, doesn't delve too deeply into the racial and sexual revelations that made Portrait of Jason such a sensation. Leaving to Clarke what is Clarke's, Winter instead mostly grapples with the theme of truth, particularly in documentary film. After hours of filming, Shirley tells Jason that she barely has any usable footage, and wonders if he has been depicting himself as he wants to be seen. A boisterous, lively performer, Jason bristles and barks and emotes with aplomb when the feeling strikes, but mostly, he's the definition of an uncooperative subject, worrying more about when and how much he'll be paid, and where he can get his next high (that exchange is one of the film's more pointed racial explorations).
Schulman and Waters both deliver strong performances. Schulman buries Clarke's directorial authority in a flexible nonchalance, often speaking on the verge of a monotone, (mostly) knowing how to respond to Jason in all of his quickly-changing seasons. The film is mostly a showcase for Waters, who gets to play with stereotypes and also gets to chew some scenery, singing and dancing and lying on the floor. He's a powerhouse performer who, following this debut, will hopefully go on to even greater things.
I hope the same is true for Winter, who crafts an interesting, but ultimately unsatisfying film here, his first feature since 1997's Chocolate Babies. He clearly shares passions that outspoken lovers of film are vocal about: female directors, the representation of minorities on screen, queer characters of color. Jason and Shirley feels like a passion project through and through, the sort of small, specific film that might not find a wide audience, but will hopefully stir something deeply in those who see it.