Please allow me a moment to commiserate with the subject of a documentary by director D.W. Young, photographer James Hamilton. Toward the end of the film, “Uncropped,” Mr. Hamilton, talks about his stint at the New York Observer and, in particular, when it changed ownership. The paper underwent significant alterations after Jared Kushner — yes, that Jared Kusher — bought the Observer from its founding publisher, Arthur Carter.

An owner has every right to do as he sees fit with his enterprise, but for many of those who worked at the paper — I was an art critic there for a good decade — Mr. Kushner’s purchase heralded mixed tidings. Disagreements about politics were the least of it; pay and editorial purview figured into our worries. So, when Mr. Hamilton tells of the joy he experienced when his foot was run over by a truck at a Brooklyn intersection, I couldn’t help but laugh. Significant bodily injury provided a viable reason for one staff member to up and  leave the Observer.

Those familiar with Mr. Hamilton’s photographs — and it’s difficult to imagine longtime New Yorkers who aren’t familiar with them — will know him primarily from his tenure at the Village Voice, where he worked for close to 20 years. A good portion of the film is dedicated to the Voice — more than is good, I think, for the ostensible subject of the movie — as well as the vital role the alternative weekly played in the city’s life and culture. Those who came of age thumbing through the paper’s inky pages will undergo a pang of nostalgia revisiting its halcyon days.

“Uncropped” is the latest addition to a cinematic sub-genre I’ve come to call “Boomer Lamentations”: that is to say, films that pine for the good old days of second-hand bookstores, record emporiums, semi-affordable apartments, an upstart music scene, and an abundance of repertory movie theaters. Bohemia, in so many words, and one is reminded of how far we’ve come — or, perhaps, sunk — upon seeing brief footage of the Strand Bookstore. Praise the Lord it’s still in business, but, then, even the Strand isn’t what it used to be.

Cynics of a certain age like to grumble — as they do during “Uncropped.” Mr. Hamilton’s Village Voice colleague, photographer Sylvia Plachy, bemoans how the digital age has robbed us of face-to-face contact with one’s colleagues and, concomitantly, a workplace one could call home. 

Mr. Hamiton is a low-key and affable guy, a man who likes to take pictures and doesn’t use up much oxygen in the room. At several points during “Uncropped,” you get the distinct feeling that he’d rather be anywhere except in front of Mr. Young’s camera. Still, Mr. Hamilton’s skills found him traveling to many fascinating places and some dangerous events — revolutions, wars, and the crack-infested streets of 1980s New York City among them. An inveterate movie buff, Mr. Hamilton’s encyclopedic knowledge is daunting. That may go some way in explaining why celebrity portraiture is his strong suit.

Mr. Hamilton’s street photos, however adroit, take a back seat to those of Martha Cooper, Helen Leavitt, and Lee Friedlander — clear influences, all. But, then, Mr. Hamilton would probably tell you the same thing. As it is, he’s provided signature images that you forgot you remembered: of B.B. King, Jack Nicholson, David Lynch, Joni Mitchell, an ebullient Alfred Hitchcock, and a stern Bing Crosby. 

Mr. Hamilton has woven himself, with consummate modesty, into the grain of New York City. “Uncropped” proves a wayward testament to his gifts.