“Bill Cunningham New York” chronicles a man who is obsessively interested in only one thing – the pictures he takes that document the way people dress. Bill has lived in the same small studio above Carnegie Hall for fifty years, never eats in restaurants and gets around on a worn-out bicycle– his sole means of transportation. The contradiction of his monk-like existence and the extravagance of his photographic subject matter is one aspect of his private life revealed in the movie.
The film’s cast of characters ranges from the downtown New York eccentrics Bill has photographed over the years to the uptown fixtures of New York culture (Tom Wolfe, Anna Wintour, etc) and pillars of “New York Society” who have never before appeared in a movie but who agreed because of their regard for Bill (David Rockefeller, Brooke Astor, Annette De La Renta, among others). The range of people reveals something of the delirious and delicious romp through New York that composes Bill’s world.
A sartorial Weegee, habitually dressed in a blue work jacket, Bill Cunningham has tried to live his life as an unencumbered man. He wants only his independence to be able to point his camera when beauty crosses his path. With this singular goal, he has managed to create a poignant and ongoing chronicle of the intersection of fashion and society in New York over fifty years — in effect, a portrait of New York City itself. [Synopsis courtesy of official site]