Bill Cunningham New York

Well into his 80’s, Cunningham is a workaholic maverick photographer who prowls New York on his bicycle, photographing the trends he sees on the city streets for his regular On The Streets column in the New York Times. Cunningham is not interested in celebrity, for him it is all about the clothes, the fashion, and as such he is also a historian of sorts whose photographs become a record of various trends across the ages. At night he attends fashion shows and lavish society gatherings.
 
Despite his reputation though, he enjoys a modest lifestyle. He dresses frugally, and lives in a rent controlled small apartment in Carnegie Hall, which is crammed with filing cabinets full of the negatives of every photo he's ever taken. But with the iconic concert hall about to undergo renovations, the management are in the process of evicting him and several other long-term bohemian residents that have called the place home for decades. This subplot adds a poignant note to an otherwise bubbly and relatively lightweight documentary.
 
First time feature filmmaker Richard Press took several years to gain the trust of the reclusive, private Cunningham, and the result is an intimate, warm and affectionate documentary that gives us a glimpse into his life. Press and his cinematographer Tony Cenicola follow Cunningham through his busy working days, detailing his professionalism, his meticulous eye for detail, and his long work hours that would wear out a man half his age. And despite having led a similarly hectic lifestyle for the past four decades, the enthusiastic, energetic Cunningham shows no sign of slowing down. Press also draws upon some archival footage to give Cunningham’s life some context. We briefly learn about his early career as a milliner but get only scant details about his family, who, it seems, were disapproving of his interest in photography. Although happy to let the cameras follow him, Cunningham seems a little reluctant to talk about his sexuality, the importance of religion, and how his obsession with filming fashion trends has left him little time for a personal life or relationships.
 
What comes across is a portrait of an unassuming, humble, warm, perennially upbeat and genial man with a self-effacing sense of humour who obviously loves what he does. Such is his reputation and status amongst New York’s elite that the likes of legendary Vogue editor Anna Wintour, the elderly and colourful Iris Apfel, socialite Annette de la Renta, designer Michael Kors, and novelist Tom Wolfe happily sing his praises on screen.