Watching Portrait of Jason was a cross between sitting in a room with your favorite aunt or uncle, listening to them tell interesting, engulfing stories and a social experiment. Jason Holiday is the center and sole subject of this documentary. He is a former “houseboy,” hustler and aspiring nightclub act.
In the beginning, Jason entertains everyone with stories of orgies, jazz singers, hustling and working as a “houseboy.” However, as the documentary progresses you can’t help but feel a little sadness for this man who eventually begins to tell stories of rejection from family and loneliness due to hustling so many people.
Although, I have mixed feelings about this documentary, I still think it’s worth the watch and conversation.