Terminal Bar, located across the street from the Port Authority Bus Station, was once known as the roughest bar in New York City.

But Sheldon Nadelman—who, in the ’70s and ’80s, worked at the dive his father-in-law owned—doesn’t think that’s quite true. It was certainly rough—frequented by pimps, prostitutes, and drag queens—but it wasn’t the roughest.

Mostly, he said, his customers just needed a place to go in a world that wasn’t always hospitable. And Nadelman would know: He got to know his customers better than most barkeeps in the city. Besides pouring drinks for them, he also took their portraits.

“After 10 years I had a couple thousand portraits. It was simple as that. I was on a mission—don’t ask me why,” he said.

And while Nadelman calls himself a “half-assed artist,” his photos are really quite beautiful, capturing in black and white a wide cast of characters and the occasional bar. They’re now collected in a book, Terminal Bar, out last month from Princeton Architectural Press.

“In the beginning it was just the regulars and they were willing and able to be photographed,” Nadelman said. “Then there were just faces that came in and I knew I wouldn’t see them again. But they looked interesting. I’d say 90 percent of the people were willing to be photographed.”

Nadleman worked at the bar until 1982, when it closed. Then he opened his own bar in New Jersey. After that closed, he got a job at a photo lab, where he worked for the next two decades.

After living in the city for 40 years, Shelly has stopped going there almost completely. (“We’re divorced,” he says of Manhattan). Meanwhile, the Times Square area changed drastically. The space where Terminal Bar once stood is now occupied by the headquarters of the New York Times.

After lying mostly dormant for years, Nadelman’s photos finally saw the light of day after his son, Stefan Nadelman, digitized his negatives, and then created a documentary about them, which won the 2003 Sundance Jury Prize, among other awards.

Nadelman remembers Terminal Bar with mixed emotions: His time there was pivotal in his development as a photographer, but he said it was often disturbing to look on as many of his customers (and subjects) “destroyed themselves” with alcohol. And while his photos have inspired much interest about a place that, in many ways, represents an era of New York long past, Nadelman claims not to completely understand the nostalgia.

“My father-in-law loved the place,” he said. “I can’t imagine anyone could love a stinky bar like that.”