A portrait is a delicate transaction: the subject might look at it and, shocked, see not himself but how the artist feels about him. Next week at the Portage, Northwest Chicago Film Society presents one of the most audacious character studies to come out of the American underground cinema, Shirley Clarke's Portrait of Jason (1967); like many portraits, it's most fascinating as a document of a relationship. Clarke, a Jewish heiress, made a name for herself in New York directing the hard-edged urban drama The Connection (1962); one evening in December 1966 she invited Jason Holliday, a jocular, 42-year-old gay hustler, up to her penthouse apartment at the Chelsea Hotel and, with a film crew, spent 12 hours filming him against one wall as he held forth about his wild life. Clarke never appears on camera, and her questions for Holliday are short, simple, and infrequent. Yet the finished feature, running 105 minutes, speaks volumes about what these two people had in common—and what they didn't.
The main difference between them, obviously, was money. "I've been balling from Maine to Mexico, and I ain't got a dollar to show for it," Holliday laments in the film. Born Aaron Payne in Trenton, New Jersey, he spent years working as a houseboy, and some of his funniest stories touch on the wealthy white folks he flattered and learned to exploit. One woman in the rich Nob Hill section of San Francisco took a sleeping pill every day at 1 PM that would knock her out for three hours; while she was down, Holliday would take her dog to Aquatic Park and get high with all the hustlers and drug heads. Working for another woman in New York City, he'd pop a few "sparkle-plenty pills" (the dowager who got him started on them promised they'd make him "sparkle plenty") and clean the house. "Some things I broke on purpose, some things were accidents," he confesses, recalling how he knocked over and destroyed a beautiful vase. "I used to work in sunglasses," he explains. "That's so they couldn't see what I was thinking."
Compared to Holliday, Clarke had a comfortable life: born Shirley Brimberg in 1919, she grew up on Park Avenue and attended no fewer than four colleges as she studied dancing and choreography. Her father and maternal grandfather were wealthy manufacturers, and both she and her younger sister, the writer Elaine Dundy, clashed with their father as they sought professional lives for themselves. Clarke made her filmmaking debut with a dance film, studied with Hans Richter at City College of New York, and fell in with the dynamic crowd of young filmmakers (John Cassavetes, Jonas Mekas, Stan Brakhage, Lionel Rogosin) that championed the so-called New American Cinema. The Connection, a frank depiction of drug dealers, made her notorious, and her documentary Robert Frost: A Lover's Quarrel With the World, won her an Oscar. Her family had millions, and in Portrait of Jason her presence is felt mostly through the spare, upscale apartment that becomes the set: a high white wall is bisected by a lovely mantelpiece with a bulbous glass vase atop it, and off to one side are shelves minimally decorated with art books, a decanter, and a little human skull.
Clarke shot in black-and-white, and the contrast between the gleaming white backdrop and her dark-skinned subject is arresting. Her takes are continuous, and you can hear her ordering the sound man to keep the tape rolling even as the screen goes black and the camera man changes magazines. Holliday is inexhaustible, roaring with laughter as he shares his stories, and typically Clarke ends each take by blurring the focus and cross-fading to a new shot. As the night goes on, Holliday smokes, drinks, puffs on a joint, and eventually latches onto a bottle of scotch, which he sucks at periodically. Eventually other voices can be heard off-camera, in particular the actor Carl Lee, who begins firing contemptuous personal remarks at Holliday. The film reaches its climax when the two men argue and a tearful Holliday protests bitterly, "If you don't know that I love you, man, then you don't know anything about anything."
Portrait of Jason is embraced now as a cornerstone of LGBT filmmaking, and you can understand why: despite his tragic streak, Holliday is full of life, proudly gay, and brutally, disarmingly frank about his sex life. "As you know, I'm an experimental queen," he quips, rattling off the sort of kinky services he offers his johns. For ten years he's dreamed of becoming a cabaret performer, and with some money from a sugar daddy he's hired a pianist and put together a singing act. At one point he busts out "The Music That Makes Me Dance" from Funny Girl, and he's pretty good; donning a feather boa, he impersonates Mae West and Pearl Bailey and he's pretty awful. Holliday exults in the attention of having cameras on him, and he seems to realize that this little project may be the biggest thing that will ever happen to him: "This is my chance to really feel myself, and say, 'Yeah—I'm the bitch.'" He chuckles and smokes. "Believe it! You amateur cunts take notice: I'm the bitch!"
Knowing how Clarke grew up, you can't help but wonder what Holliday might have accomplished with the sort of advantages she had. Yet Clarke was drawn to subjects like Jason Holliday precisely because, despite all her money, she felt marginalized herself—written off as a woman, written off as a dilettante. "I identified with black people because I couldn't deal with the woman question and I transposed it," she told interviewer DeeDee Halleck in 1985. "I could understand very easily the black problems, and I somehow equated them to how I felt." With great resentment, she would recall being interviewed for a job by the legendary exploitation producer Roger Corman and realizing that he had no idea who she was. By the time she died in 1997 (a year before Holliday), her work had fallen into relative obscurity, though a recent initiative called the Shirley Clarke Project has begun to restore, distribute, and celebrate her early classics, including Portrait of Jason.
Interviewed in 1983, Clarke recalls that she went into the shoot hating Holliday but fell in love with him as the hours passed, and nowadays Portrait of Jason is debated as an example of cinema verite because Clarke so tacitly indulges Holliday's drama queen instincts, letting him turn a documentary into a one-man show. After a while you begin to wonder how much you're being hustled here, and whether Holliday might not see Clarke the same way he does the rich whites he doted on as a houseboy: "They think you're just a dumb, stupid little colored boy and you're trying to get a few dollars, and they're gonna use you as a joke. And it gets to be a joke sometime as to who's using who." The blurred line between truth and fiction, between portrait and self-portrait, makes Jason a fascinating experience long after he and Clarke went their separate ways.