The famous BilL Cunningham has been roaming the streets of New York for over fify years. This Schwinn-riding cultural anthropologist has been obsessively and inventively chronicling fashion trends and high society charity soirées for the Times Style section in his columns “On the Street” and “Evening Hours.” Documenting uptown fixtures (Wintour, Tom Wolfe, Brooke Astor, and David Rockefeller— who all appear in the film out of their love for Bill), downtown eccentrics and everyone in between, Cunningham’s enormous body of work is more reliable than any catwalk as an expression of time, place and individual flair. In turn, Bill Cunningham New York is a delicate, funny and often poignant portrait of a dedicated artist whose only wealth is his own humanity and unassuming grace.
Bill Cunningham New York is Richard Press’ feature film debut. He has written and directed several award-winning short films, including 2÷3, which premiered at the New York Film Festival and received a jury prize at The Berlin International Film Festival; Rambles and Expecting, both of which premiered at The Berlin International Film Festival. His film project 
Virtual Love, developed at the Sundance Filmmakers Lab, received the Sundance/NHK award at the 2005 Sundance Film festival. He is at work on The Farnsworth House, a narrative film that he wrote and will direct about the scandalous romance between architect Mies van der Rohe and his client, Edith Farnsworth.
Bijan Tehrani: How did you come across the subject of Bill Cunningham New York?
Richard Press: Well, you know, I grew up in New York City and I grew up reading the New York Times and the Sunday times and I followed Bill’s columns since I was a kid and I just never knew who he was and never knew what he looked like. About ten years ago when I first started making movies, I was actually working at the New York Times as an art director and I worked with Bill on one of his pages. Therefore, I knew him professionally that way and soon after meeting him I just thought, “Oh my god, this person is a singular individual and someone should make a movie about him!” And that was my initial influence to make this film. While I think his work is really important, my inspiration for the movie was really the matter of who Bill is, as a person, and trying to capture how he is trying to live his life, his work ethic, and his religious obsession with what he does; that was really the influence for the film.
BT: Bill Cunningham New York deals with the Bill’s character rather than telling the story of his life. I have to tell you, this is one of the reasons I appreciated this film. Why did you choose this angle for your film?
RP: Well, thank you for appreciating that—it is very gratifying. The biographical details of Bill’s life were not so much as interesting to me as finding out who this man is. I was not interested in making a biopic, I was really trying to capture something a little less tangible; to show Bill Cunningham’s spirit and his essence. I wanted to show who he is through his work and the people he photographs and the way he documents the New York City.
BT: When did you start shooting with him and how did you work with Bill?
RP: Well the movie was made in a very unconventional way. There was no “movie crew” per say, and there was no sound person or boom operator. Bill would never allow a movie crew to follow him around, so it had to be a very intimate situation. I had never been a cinematographer on my own movies, but I shot this film along with Tony Senatolla who is a staff photographer at the New York Times. He actually has never shot a movie but Bill knew, trusted, and liked him, so we did it that way. And then Phil, the producer, has known Bill for 15 years because Phillip was an editor at the New York Times—so it really was the three of us. I used very small cameras that did not even look like professional camera to film all of the cinema vérité footage, so it did not even look like we were making a movie it just kind of looked like we were hanging out with him.
BT: Can you tell us about the old footage used in your film?
RP: I came across the old footage when I was trying to find any kind of archival footage on Bill. The old footage is actually part of a small in-house movie that was made at the New 
York Times about women fashion editors, and Bill was interviewed for that film. Bill had agreed to appear in that old in-house film only if he didn’t talk about himself, but about other people. Finding that old footage was like discovering a gold mine, it showed that, thirty years ago, Bill looked almost the same as he does now! It shows that he has kept his passion and joy for what he is doing. Both archived footage and new footage show that he is simply so true to himself and he is just doing the same thing.
BT: Was there any trick to dealing and making him confortable in front of the camera? Also, how much of the film was structured in the editing room?
RP: There is an inside joke that it took 10 years to make the movie, and eight of those years were spent trying to convince Bill. He is a very reluctant subject; he is completely modest and humble and doesn’t think he deserves any kind of attention. Even when he agreed to appear in our film, he did not quite agree and there was always a bit of a negotiating going on. It was a bit of a dance, trying to get his cooperation to let us film him going on his rounds on his bicycle.
About shaping the film, part of the movie was structured in the editing room and it was really a reflection of Bill, revealing himself as a person over-time to us. That became one of the narrative threads throughout the movie.
BT: Was the creation of the film a process of discovery for you? It seems as though you were uncovering a lot of new information during the shoot.
RP: Yes absolutely, I really did not know anything about him personally. I knew that he lived in Carnegie Hall and I had no idea that his apartment was the way it was. I did not know anything about his neighborhood, and I didn’t know about him being evicted from his studio. I knew Bill worked hard, but I had no idea how singularly devoted he is to his work, and that really is all he does. Therefore, all of it was really a surprise, a delicious surprise. There were people in the movie and they say they have known Bill for 30 or 40 years, but they don’t know anything about him because he is just very private.
BT: Every filmmaker should love the subject of his or her film in order to make a successful film. What drew you to this film, Bill’s life, and his attitude toward his art?
RP: I think Bill has lived his life on his own terms and he has just dedicated his life to doing something that he loves, and loves for the right reasons; he is not looking for fame or fortune or any kind self-aggrandizement. He takes pictures for the pure joy of doing it and sharing it with other people.
BT: How did you come up with the final visual structure of the film?
RP: As I was shooting, I was starting to see certain narrative threads emerging, so I started to follow those threads as I was shooting the film. I really did not know anything in terms of the structure of the film until I got into the editing room. I had a wonderful editor, Ryan Denmark, and we just locked ourselves in an editing room for over a year to create the 
movie.
BT: Has he seen the film since it was finished?
RP: No, Bill has not seen the film. We tried to get him to see it, but he knows what’s in it and he has given us his blessing—he just says that he is too busy.
BT: What has the reaction been to Bill Cunningham New York?
RP: The reactions have been really great. People just seem much moved by him, and it really is all about him as a person in the most practical sense. We were told that it is breaking all of these box office records in New York.
BT: Any future projects lined up?
RP: Yes, it is actually about another artist and it’s called the Farnsworth House. It is about a scandalous love affair that Mies van der Rohe had with his client Edith Farnsworth that occurred during the building of the first glass house in Chicago, the Farnsworth House. They went from being lovers to being brutal enemies and suing each other, so it’s really about all of the blood on the floor and the creation of this masterpiece.