'Jason and Shirley': Outfest Review

Courtesy of Jason and Shirley
This look at the making of a landmark doc is only intermittently effective.

Director Stephen Winter recreates the meeting of indie film pioneer Shirley Clarke and male hustler Jason Holliday as they shot acclaimed doc "Portrait of Jason."

At a time when the press has zeroed in on the very few women directors working in film, a movie that highlights a female pioneer is of special interest. Jason and Shirley, which has been making the gay festival circuit, centers on Shirley Clarke, an indie filmmaker who won an Oscar for directing a documentary about Robert Frost in 1963. Her narrative movies — The Connection and The Cool World — were grittier examinations of drugs and race in American culture. In 1966, she decided to do a feature-length interview with a black gay hustler, and the finished film, Portrait of Jason, was controversial but memorable for exploring a side of American life that was definitely under wraps.

The protagonist of her film, Jason Holliday, is less remembered than Clarke. But Stephen Winter, the director of this new movie, clearly wanted to give equal attention to the groundbreaking filmmaker and her outspoken subject. He succeeds only intermittently, which means the film has limited commercial potential.  But it’s intriguing as an attempt to honor a milestone in the early indie film movement.

The film takes place over the course of the day that Clarke filmed her interview with Holliday at the Chelsea Hotel in New York. It starts out with Clarke and her small crew waiting impatiently for Jason to arrive. When he finally saunters in, he seems determined to take charge of the interview and present the image that he wants to convey. A battle of wills ensues, in which there is no clear winner.

Winter seems respectful of Clarke, though he presents her as something of an opportunist who will try anything to get the naked truth that she seeks. This is probably an accurate picture of the single-mindedness of most artists, but some of Clarke’s admirers have understandably objected to the portrait. However, Sarah Schulman gives a skillful and engaging performance.

But the main reason to see the film is for the performance of Jack Waters as Holliday. (Waters and Schulman co-authored the script with Winter.) Sly, charismatic, alternatively evasive and bluntly honest, Holliday captures the unpredictability of a man who refuses to conform to anyone’s sexual or racial stereotype. Any documentary interview is going to be something of a mating dance between director and subject, and the film makes it clear that Clarke met her match when she invited Holliday to perform for her camera.

There are a few other characters in the piece, including Clarke’s cameraman and sound engineer, Jason’s drug dealer and an actor friend whom Clarke enlisted to try to break down Holliday’s resistance. But these characters don’t register very forcefully. There are also a few arty flashback or fantasy sequences that dilute the central narrative. The camera work is only serviceable, and the musical score by Drew Brody is overbearing. In the end, the film fails to do justice to its subject, but Waters’ performance is definitely worth a look.

Cast: Jack Waters, Sarah Schulman, Tristan Cowen, Eamon Fahey, Tony Torn, Mike Bailey-Gates, Orran Farmer

Director: Stephen Winter

Screenwriters: Stephen Winter, Sarah Schulman, Jack Waters

Producers: Stephen Winter, Ned Stresen-Reuter, Bizzy Barefoot, Jason Ryan Yamas

Executive producers: M. Blaine Hopkins, Jake Perlin

Cinematographer-editor: Ned Stresen-Reuter

Production and costume designer: Bizzy Barefoot

Music: Drew Brody

No rating, 79 minutes