Directed by Shirley Clarke • Documentary • 1967 • 108 minutes

On the night of December 2, 1966, Clarke and a tiny crew convened in her apartment at the Hotel Chelsea to make a film. There, for twelve straight hours they filmed the one-and-only Jason Holliday as he spun tales, sang, donned costumes and reminisced about good times and bad behavior as a gay hustler, sometime houseboy and aspiring cabaret performer. The result is a mesmerizing portrait of a remarkable, charming and tortured man, who is by turns hilarious and heartbreaking.

Ingmar Bergman called it “the most extraordinary film I’ve seen in my life.” When it first screened in a sneak preview, the audience included Tennessee Williams, Robert Frank, Thomas Hoving, Amos Vogel, Norman Mailer, Andy Warhol, Arthur Miller, Elia Kazan, Ruby Dee, Ossie Davis, Rip Torn, Geraldine Page and Terry Southern.

PORTRAIT OF JASON is also a potent reminder of what the world was like for black gay men in the heat of the Civil Rights movement and before the Stonewall Uprising. Holliday talks about serving time at New York’s Riker’s Island jail after propositioning (or being propositioned by) an undercover cop. And his observations on the casual racism he experienced are funny, stinging, and painful.

People fell in love with Jason Holliday in 1967. In 1995, Marlon Riggs asked the question in his brilliant Black Is…Black Ain’t, “How long, Jason, how long have they sung about the freedom and the righteousness and the beauty of the black man and ignored you. How long?”