Bill Cunningham New York (2011)

Thanks to newbie director Richard Press, I’m in love with a man more than twice my age. The object of my affection is the eponymous subject of Bill Cunningham New York, an octogenarian fashion photographer for the New York Times.

Then again, fashion photographer may not be the right term. As Cunningham tells us in this documentary look at his life and career, he hardly considers himself such. He has neither a studio–unless you count the middle of Fifth Avenue with taxis whizzing by–nor models. He has street muses: the men and women of New York City who get dressed with the kind of energy and originality that have demanded to be chronicled in the Sunday Styles section of the paper every week for the last 40 years.

As a documentarian of sorts himself, Cunningham makes an unlikely subject for this type of film. He has spent his entire career shunning money and fame, although such luminaries as Anna Wintour and the late Brooke Astor count him among their friends and fashion idols. His devotion to being the man behind the lens is so dogged that he sometimes still gets cussed out by women on the street for being a dirty old man taking their photos. Even those who have known him longest couldn’t tell you where he was born, whether he was raised rich or poor, and what his sexual orientation is. He’s a rare and dying breed in our world of self-obsessed culture, where talent means little and biography is all.

Bill Cunningham New York attempts to peel back a layer of that uncontrived mystery. The film functions as respectfully, if not quite as insightfully, as its subject. Only Press and his cinematographer Tony Cenicola, also a photog for the New York Times, follow Cunningham on his daily bike rides uptown and downtown to track fashion. Their hands-off style allows us to see the man in his element, racing after a woman in a sequined cocktail dress and almost getting hit by a car without even noticing, for example. That footage is intercut with interviews of those who know him, including the delightfully daffy celebrity photographer Editta Sherman, who has shared residence in Carnegie Hall with Cunningham for decades.

We learn that, up until he was evicted a few years ago, Cunningham lived in a tiny artist’s studio in Carnegie Hall, surrounded by filing cabinets of every roll of film he’s ever shot. Other than that, his worldly belongings seem to include only a twin size mattress, a ton of fashion books and magazines, and a classic Schwinn (his 29th, the first 28 having been stolen). His wardrobe consists of a tuxedo for when he photographs evening charity events, a pair of khakis, and a few blue smocks with plenty of pockets for film. He purchases them for $20 from the same discount store where Parisian street cleaners buy theirs.

Yet this man with the Buddha-level ascetic lifestyle is also a congenial bon vivant with a bygone Yankee drawl and a quick and easy laugh. He may take his meals alone (the cheaper, the better) but the whole world tickles, inspires, and engages Bill Cunningham, especially “the kids” in their brightly colored clothes, sky-high heels and avant-garde makeup. Press’s documentary reveals that Cunningham began his career as a milliner in the 1950s and moved on to writing and photographing for Women’s Wear Daily and the original Details magazine before beginning his long stint at the Times.

It’s the length and depth of his career that makes Bill Cunningham New York such a fascinating picture to watch. Cunningham is the last of a generation. He was there when Dior unveiled his New Look after the first World War and has watched the evolution of everything we consider fashion–from the Paris couture shows he attends each year, to the eveningwear styles of the rich and famous (though he’s so uninterested with celebrity he can’t remember most of their names), to the urban street-wear trends he was the first to realize were worth following. As such, his knowledge is encyclopedic. He can reference 18th century theatre costumes and John Singer Sargent paintings in one breath, gay underground club kids in the next, and connect them all through Yves Saint Laurent for good measure.

Still, there’s a way in which we don’t get to know the subject of Bill Cunningham New York. In one scene, Press asks Cunningham about whether he has had any romances in his life. Cunningham laughs warmly and asks, “Are you asking me if I’m gay?” That he answers the question with such a disarming, but guileless, question of his own tells you everything you need to know about the man and his work.