Though Bill Cunningham’s weekly fashion photo spread “On the Street” had been a mainstay of the New York Times for over two decades by the time that Richard Press’s Bill Cunningham New York premiered in 2010, the documentary was many people’s introduction to this singular personality. Photographer, ethnographer, and fashion historian, Cunningham would occasionally stop by a fashion show or a glitzy soiree to grab a few pictures of the latest haute couture styles. But he was more in his element on the streets of New York, which he’d traverse on his trademark bicycle, snapping photographs of passersby with one of his old-school Nikon cameras. Though essentially a conventional profile documentary, Press’s film lingers in the mind thanks to the fascinating peculiarity of its subject: a painfully shy ascetic who found a joy in his work that he denied himself in all other aspects of his life.
Mark Bozek’s The Times of Bill Cunningham—largely consisting of footage from a lengthy and wide-ranging 1994 interview with Cunningham, fleshed out with archival photos and some voiceover narration by Sarah Jessica Parker—offers a broader overview of Cunningham’s life than Press’s film. It covers everything from his early days as a milliner to his work with Chez Ninon on Jackie Kennedy’s wardrobe to his time spent cataloguing the preparations for each of Diana Vreeland’s legendary exhibitions at the Museum of Modern Art. But it also ends up covering much of the same ground as the earlier documentary, including Cunningham’s legendary frugality, his shocking disinterest in his own wardrobe, and his cave-like apartment above Carnegie Hall. The shadow of the earlier film looms so large over Bozek’s that one of the most revealing moments in the latter is an anecdote about the former: When Bill Cunningham New York premiered in New York City, Cunningham photographed attendees on the red carpet but refused to attend the screening and never saw the film himself.
Throughout the interview, Cunningham’s smiley self-effacement belies his serious contemplation of fashion and its place in the world. Cunningham saw himself not as an artist nor as a journalist but as a historian, a documenter of politics and social upheaval as reflected in the things people wear. And Bozek’s film hints at the deep sadness and loneliness Cunningham appears to have lived with his entire life; when pitched a relatively innocuous question about what, if anything, makes him sad, he immediately chokes up before revealing his deep despair over the AIDS epidemic. Later, the film notes that, after his death, it was revealed that the pinchpenny Cunningham had donated millions of dollars to both the Catholic Church and various charities combating the epidemic.
There’s an obvious tension between those two recipients of Cunningham’s generosity—one so strongly tied to the gay community and the other such a fierce opponent of gay rights—but the documentary never probes the man’s conflict between his faith and his ties to gay activism, if there was any in the first place. Rather, Bozek emphasizes the latter, noting Cunningham’s pioneering coverage of New York’s pride marches, while largely avoiding any discussion of the former. (Cunningham, widely rumored to be gay, once deflected a query from Press about his love life, claiming that the question of whether he might be gay had never even occurred to him, and he seemed to have lived a life completely devoid of romantic encounters.)
The Times of Bill Cunningham is content to offer a largely breezy survey of its subject’s life and legacy, one that’s informative and, thanks to Cunningham’s garrulousness, frequently delightful. But Bozek often undermines his subject’s natural charm with some clunky, even amateurish, filmmaking—cheesy Moby needle drops, awkward Ken Burns-style pans over digitally pixelated photos, and a flowery, superficial narration that feels directed more at the Manhattanite fashion elites who desperately craved to have their photo appear in one of Cunningham’s pieces in the Times than to the broad, popular audience for whom those pieces were designed. Cunningham was always the consummate outsider in an insider’s world, recording ritzy, hyper-exclusive events while refusing so much as a glass of water.
At its best, The Times of Bill Cunningham gives its subject the space to lay out his deeply populist vision of fashion, one that maintained a skeptical distance from the designer-driven, top-down approach taken by magazines such as Vogue. At its worst, however, the film undermines Cunningham’s egalitarianism by linking him directly with the kind of elite snobbery and wealth fixation he abhorred. When Parker starts fawning over the monetary value of the artworks and diamonds discovered in Cunningham’s apartment after he died, or approvingly cites Anna Wintour’s famous quip, “We all get dressed for Bill,” you can practically hear the legendarily humble Cunningham rolling over in his grave.