Fifteen years ago, when City Paper last published a retrospective of staff photographer Darrow Montgomery’s work—to commemorate his 15th anniversary at the paper—our cover description read, just over his name, “Excerpts 1986-2001.” Heavy-hearted readers wrote in to say how tragic it was that such a talented young prodigy had died. (So maybe the type treatment was ill-considered.)

Fortunately, he had not then, nor has he yet, shuffled off this mortal coil. He’s still with us, and on the anniversary of his 30 years here, we (mostly he) have combed and culled and curated a selection of some of his most memorable work. Montgomery has quietly narrated the essential story of D.C.—not the feds, the tourists, or Congress, but the stories of the real city, the one teeming with characters, crime, and gentrification. Among other things, he knows where the wig stores used to be, the ones supplanted by J. Crew storefronts.

“He seems to tell us who we are, and if you look through the photos you get a portrait of who we are that’s not obvious, that’s below the surface,” says Jason Cherkis, a former City Paper staffer who’s now a reporter for The Huffington Post. “We know the yoga mat brigades that have invaded the city, but … he’s looking at the slow evolution of D.C. I feel like it’s sort of sacred.”

Montgomery first found his way here as an intern studying at Corcoran School of Art and worked under the tutelage of then-editor Jack Shafer, now with Politico. At one point, Shafer put the lanky young lensman on probation for casting too many shadows in his shots. It didn’t last.

And when other unsure, unshaped talents showed up, Montgomery knew a little something about how to bring them along. “I spent the majority of my time at City Paper just scared off my ass,” says Ta-Nehisi Coates, author and national correspondent for The Atlantic who got his start here. “The thing he gave me most was courage. He’s such a soothing presence.”

Coates recalls working on a story once about a troublesome panhandler. “It was deeper than that, as all City Paper stories are, but I was like, ‘There’s no fucking way this guy’s gonna talk to me, much less let us get a picture.’ But Darrow got that picture. Darrow knew the guy was gonna be fine. I was really so new to everything.”

At no point have Montgomery’s tools been the latest and greatest, perhaps fortuitous considering how many times he’s been robbed and burgled. At one point in the 1980s, Montgomery was using a Speed Graphic camera that was 40 years old even then. He’s navigated dark rooms and the digital revolution, trampled through the woods in search of Sasquatch, documented murders and the election of the nation’s first black president.

“Darrow … does not truck in easy stereotypes or cheap sentimentality,” says writer Eddie Dean. “He goes straight to the soul of his subjects, and his most enduring subject is the city of Washington, D.C. His photographs are a lifelong poem to the city and to its people. An assignment with Darrow was always an adventure, and he always got the goods.”

And always softly. He can calm even the tensest, most disagreeable room, make small talk with prostitutes and pimps, suits and drag queens, grandmas and skaters. “Going out on shoots with Darrow, he lowered the emotional temperature,” says Michael Schaffer, a former City Paper editor who now helms Washingtonian. “He would small talk with them, and he wasn’t asking questions. He was just working.”

As Amy Austin, City Paper publisher emeritus puts it, “He’s the guy. He’s always the guy”—the one writers want to work with, the one subjects feel easy with, the one beer lovers want to drink with. More than that, “You see a Darrow photo and you immediately think of City Paper.”—Liz Garrigan

Photographs by Darrow Montgomery