It’s impossible not to notice the film’s gaping lack of tension and conflict, largely consisting as it does of surveillance-esque footage of Cunningham doing his thing: shooting photos of Manhattan’s finest sidewalk fashionistas like a bubbly papparazo. But the spectacle of Cunningham doing everything from run into traffic to hiding behind flowerpots to get that perfect shot is sufficiently fascinating to behold.
The film awkwardly juxtaposes images of the upper-crust society that Cunningham still circles—Brooke Astor’s 100th birthday party being a major highlight—with director Richard Press grilling Cunningham about his personal life, creating an uncomfortable shroud of mystery. It’s clear from the get-go that Cunningham feels uncomfortable talking about anything but his work, and while Press’s attempts to get the audience more acquainted with the man behind the camera are admirable, watching Cunningham mumble awkwardly about his lack of romantic relationships and rumors of homosexuality are more squirm-inducing than anything else.
Bill Cunningham New York amounts to the antithesis of last year’s Anna Wintour-fueled (and oddly enjoyable) bitchfest The September Issue. Gone is the self-importance of the high and mighty print fashion publication and obsession with waifish models. Cunningham himself wears a cheap blue poncho as his uniform of choice, and at one point rails against fashion that isn’t accessible for everyone. “It’s all about the clothes,” he emphasizes, not the way the person who wears them looks without them. He certainly couldn’t be more right, and it’s this lack of pretension on the part of both subject and director that makes this slightly fluffy if nevertheless fascinating documentary mesh together just so, somehow glamorous and humble at the same time.