Review: The Times of Bill Cunningham Discovers the Man Behind the Photographs

In 2011, I saw a wonderful documentary about New York Times “On the Street” photographer and fashion historian Bill Cunningham called Bill Cunningham: New York. At the time, Cunningham was still very much alive, negotiating the streets of New York on his bicycle looking for examples of and trends in fashion on ordinary people. He was given a full page every week in the newspaper to provide dozens of examples of the latest looks and colors that seemed to be dominating the city’s fashion sense. He saw himself as more of a chronicler than a photographer, but in truth, he was both.

Times of Bill Cunningham Image courtesy of Siskel Film Center

Cunningham died in 2016, an event that inspired director Mark Bozek to dig out an interview he did with him in 1994. The conversation was only meant to go 10 minutes, but lasted hours and wove through Cunningham’s youth growing up in a conservative Catholic home in Boston. Not surprisingly, his decision to be a part of the fashion industry didn’t sit well with his parents, and while he never once discusses his sexuality, we have to assume that his parents didn’t want him near an industry populated by a great number of gay men. One of the great paradoxes in Cunningham’s life is that, during his lifetime, he gave millions of dollars to AIDS research charities, as well as the Catholic church.

Using the 1994 interview as the blueprint for the documentary, the film journeys through Cunningham’s years as a milliner, a passion that was borne out of observing the ladies in church in their elegant hats. In his time in this profession, he dressed a who’s who of famous heads, including Marilyn Monroe and Ginger Rogers. He eventually moved into the famed apartments over Carnegie Hall and had neighbors like Marlon Brando, Norman Mailer, and Leonard Bernstein; and before long, he was convinced to move out of crafting fashion and into photographing it.

He become known among the elite in show business, fashion and everything in between, and while he wasn’t a big fan of portrait photography, he did still cover social events where he could capture the rich and famous in their natural environment, not necessarily posing for him but being themselves. Narrated by Sarah Jessica Parker, The Times of Bill Cunningham is a wild and vibrant tour through hundreds of candid shots by the subject, and in the end, that’s the most important and impressive aspect of the film. Among the images we see are many unpublished candids from every Gay Pride Parade in New York City (he never made any of those photos public in his lifetime). Cunningham is a man you wish you could have been friends with; his warm personality and intimate knowledge of the world he photographed combined to make him ideally suited for his job. Bozek’s film is a fitting, moving, and lovely tribute to a true artist in his field.

The film opens today for a two-week run at the Gene Siskel Film Center. Director Mark Bozek and former model and fashion advocate Bethann Hardison are scheduled to be at the Film Center’s Gallery/Café for a Q&A following the 6:15pm screening on Friday, February 28.

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Steve Prokopy

Steve Prokopy is chief film critic for the Chicago-based arts outlet Third Coast Review. For nearly 20 years, he was the Chicago editor for Ain’t It Cool News, where he contributed film reviews and filmmaker/actor interviews under the name “Capone.” Currently, he’s a frequent contributor at /Film ( and Backstory Magazine. He is also the public relations director for Chicago's independently owned Music Box Theatre, and holds the position of Vice President for the Chicago Film Critics Association. In addition, he is a programmer for the Chicago Critics Film Festival, which has been one of the city's most anticipated festivals since 2013.