Stephen Winter’s Jason and Shirley dramatizes a rich subject: the filming of Shirley Clarke’s landmark documentary Portrait of Jason inside the Chelsea Hotel over a 12-hour period on December 3, 1966. In that film, Jason Holliday elaborates on his life as a gay black hustler, or, in his words, “a stone whore” who’s been “balling from Maine to Mexico.” Holliday claims to want to be a star, perhaps a cabaret performer, but, as Clarke makes abundantly clear, he’s already a significant artist: a brilliant orator capable of spinning rich, ribald tapestries of the seamy, exploitive dimension of American life that rival Ralph Ellison’s Invisible Man for their confessional intensity.
Portrait of Jason also has a legacy of controversy, predominantly revolving around the probability that Clarke exploited Holliday, which is ironic considering that exploitation is one of the film’s subjects. This hypocrisy is what Jason and Shirley homes in on, facing an immediate issue of redundancy, as Portrait of Jason is already eaten up with the humanist compromises inherent in its making, understanding even this context to be symptomatic of the racist, classist culture that torments Holliday, that wants him to assume the role of tormented negro as a way of assuaging the privileged guilt felt by people inhabiting Clarke’s white, upper-class, and, in her case, Jewish milieu.
These wrinkles of self-awareness and self-hatred are implicatively felt by Clarke nearly as acutely as Holliday, and this is partially why her collaboration with him remains so vital and morally unresolvable. Portrait of Jason is a monument not only to the African-American experience, but to the Caucasian American’s hopeless attempt to process it.
Jason and Shirley only highlights the sadism that might’ve informed Portrait of Jason’s creation, ignoring the transcendence the latter captures as inconvenient to its thesis about the latter’s creators as ugly, superficial people who may have accidentally made a classic. It’s difficult to tell what Winter and his leads and co-writers, Sarah Schulman and Jack Waters, actually think of the film they’re attempting to contextualize.
Stephen Winter’s film doesn’t earn the gall it evinces by pissing on Shirley Clarke’s masterpiece.
Schulman’s Clarke is defined mostly by the hat she wears to partially eclipse her eyes in a gesture of elusiveness. There’s no hint in her performance of Clarke’s empathy for Holliday, which is as palpable in Portrait of Jason as her manipulation of him. Schulman’s face is curled in disgust throughout, and Clarke’s always saying things that serve to retroactively editorialize her. Such as when she instructs boyfriend and collaborator Carl Lee (Orran Farmer), an old friend of Holliday’s, to “break” Holliday so that the film can have the “reality” she desires, which is to say the traditional pathos stereotypically associated with a ruined, self-hating gay black male. As Carl says to Waters’s Holliday, Clarke “wants the tour of Niggertown.”
Holliday has been even more punishingly marginalized than Clarke, reduced essentially to the “queen” role that the real Holliday played with beguiling, emotionally complicated finesse. Like Schulman’s Clarke, Waters’s Holliday is prone to artlessly summarizing the context of both Portrait of Jason and Jason and Shirley for us, whether he’s professing his desire for freedom or proclaiming that “My experience is very quickly becoming everybody’s experience.” Waters gives a livelier performance than Schulman, who’s dreadful, but he’s weirdly more irritating because we have the real Holliday available to us for contrast. We know what we’re missing.
Winter, Schulman, and Waters rarely directly recreate scenes from the documentary. Instead, they imagine the filler that Clarke presumably discarded when shaping her cut of the film. In other words, we’re watching a fantasy of unused detritus that’s meant to tell us how fraudulent these artists were in their real lives. Winter doesn’t display the confidence that the real Clarke did when she kept her camera solely on Holliday. Alternatively, the director stages a variety of limp, confessional fantasy sequences—call them Fosse-lite—in which Holliday frolics with a white woman he worked for as well as a white boy who might’ve broken his heart. It’s all so impossibly banal and garish, so insultingly broad and meaningless. Jason and Shirley doesn’t earn the gall it evinces by pissing on a masterpiece.