Almost 10 years ago, the world fell head over heels for a one-of-a-kind fashion maven, compulsive photographer, and charming eccentric. The documentary Bill Cunningham New York celebrated an elfin tastemaker who speeded around New York City on a bicycle in his trademark blue jacket, compulsively chronicling street fashion for the famed weekly New York Times Sunday Style page. Cunningham’s modesty and love for his work drew people in; his high-pitched hoot and irrepressible optimism sealed the deal. In the last few years of his life, the world was in love with Bill Cunningham.

It’s now 2020, Cunningham passed on in 2016, and a great deal has happened in fashion, photography, and the world. Mark Bozek’s documentary The Times of Bill Cunningham seeks to keep the Cunningham flame alight. The film is a fun, gossipy outing, to be sure, even touching in parts, but a little on the shallow side and lacking the scope and kinetic momentum of its predecessor. Although apparently meant as a life-affirming pick-me-up, it may also awaken deeper (even darker) reflections among some viewers about cultural shifts in the years since Cunningham’s creative peak.

The Times is largely based on an extensive, resurfaced interview from 1994, which Bozek marries sometimes awkwardly to a narration by Sarah Jessica Parker. (Note to writers: “The Nostradamus of fashion” does not mean what you think it means.) Cunningham recalls his conservative Boston childhood, his escape to New York at 19, and the day he got his first camera. Living with other free spirits in the studios above Carnegie Hall, the budding artist mixed with le tout New York. He name-checks Marlon Brando, Norman Mailer, Judy Garland, as well as dustier cafe-society names like Brooke Astor, Babe Paley, and the Duke and Duchess of Windsor. Cunningham’s mostly black-and-white photos of both the city’s famous and everyday people show off the scope and energy of his talent.

We don’t get to see Cunningham buzzing about on wheels through the city in this documentary, nor do celebrities make appearances to balance the self-portrait, so the film can feel narrow. The photographer still lets loose with his trademark self-deprecating gratitude: “I’m just a normal guy doing something I want.…It’s the greatest luxury. I love my work.” He also tirelessly boosts New York: “This city is extraordinary.” However, hints that all may not be hunky-dory surface when Cunningham suddenly breaks down in front of the camera, once in response to the AIDs crisis and once triggered by something he can’t seem to name—curious cracks in the cheery facade.

And in a way the near-tears hint at the film’s function—perhaps unintended—as an elegy: 2011 was the very last gasp before the explosion of the smartphone, which made carrying a camera 24/7 routine and reduced photographs to exponentially replenished Instagram content. The days are gone when the New York Times Style section commanded mass attention. Even trendsetting New York City seems nagged by the sense that it has lost some of what made it special. ”Everyone always thinks oh, it was better then,” declares Cunningham in a rebuke to nostalgists. “Never!”

The past may not be better, but it was radically different, and The Times of Bill Cunningham makes that difference clear. From a relatively fluffy take on a fashion fixture comes an unexpected, unspoken observation on where we’ve arrived.