How obsessive could one be about anything but still be controlled and balanced? Bill Cunningham has been obsessed with taking street fashion pictures since the 70s. The eighty-two year old is as passionate about women in interesting clothes, as forty years ago, and weaves the NYC streets on his bicycle. He is obsessed with clothes but disinterested in the celebrities, he is unsettled on the street but quiet in his own life of solitude.
Bill Cunningham shoots fashionable clothes, but could not care less about what he himself wears, at which he laughed in front of Richard Press’s camera: “It’s such a contradiction”. The contradiction of obsession and control defines Bill Cunningham’s world. Bill lives in a fantasy of fashion and beauty with his eyes, but has a workaday life at the New York Times. He spends evenings at high society extravagant social events, but his home is secluded in the file cabinet filled little apartment. In these contradictions, the personality of Bill Cunningham gradually and profoundly prevails in the bittersweet documentary.