One night in 1966, Shirley Clarke and her crew convened at the Hotel Chelsea to film self-described gay hustler Jason Holliday as he spun tales, sang, donned costumes and reminisced about good times and bad behavior. The result is a mesmerizing portrait of a remarkable, charming and tortured man who is by turns hilarious and heartbreaking.

Almost 50 years later, Portrait of Jason remains 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.