The Bowery Mission.

“This is a street that predates Manhattan. It has been one of the finest addresses in the city and it has been skid row, and now it’s changing again,” said Bill Wander, offering an extremely brief history of the Bowery.

We were standing with Mr. Wander, historian for McSorley’s Old Ale House (yes, McSorley’s has a historian), in the Bowery Hotel, surrounded by other historians, preservationists, punk rockers, poets, Italian bakers and many a downtown bar veteran who had gathered to celebrate the Bowery’s recent listing in the National Register of Historic Places.

As it happened, the Bowery Hotel was a very fitting place to contemplate the past, present and future of the formerly gritty thoroughfare. With its dark wood, velvet furniture and red-tasseled room keys, the hotel capitalizes on the nostalgic leanings of its well-heeled clientele, evoking a faded opulence that seems plausibly Gilded Age. But the hotel, which opened in 2007, is only emblematic of just how quickly that past is receding.

A historic photo of the Germania Bank Building at 190 Bowery.

The Bowery of old was a place where a person found a flophouse rather than a $400-a-night hotel, a knife fight instead of the Crime Scene Bar & Lounge. Or, as Mr. Wander put it when we asked: “I’m not quite sure what it’s becoming. But 20 years ago, drinking on the Bowery involved a brown paper bag, and now it involves a sommelier.”

It was, at this point, rather difficult not to feel self-conscious sipping the evening’s signature cocktail—“The Bowery”—a vodka, elderflower syrup, lemon juice and splash of club soda concoction served in a champagne coupe. But, we reminded ourselves as we took a sip, the occasion was a celebration. Even if it sometimes felt like a dirge.

Last month, the Bowery was added to the National Register, a designation that provided long-overdue recognition for a street that has shaped, and been shaped by, every era in Manhattan’s history—from its beginnings as a Lenape foot trail to its years as an entertainment district and, later, a punk rock mecca. The designation, however, offers little in the way of practical protections from the luxury condo era—something that neighborhood groups say is essential to preserving not only the diverse, low-rise architecture that lines the street, but the creative, freewheeling character of the Bowery itself.

“The ferocious pace of development on the east side of the Bowery is destructive,” said David Mulkins, who heads the Bowery Alliance of Neighbors, the community group that is leading the preservation effort alongside Two Bridges Neighborhood Council.

“I think the planning commission at this point has not considered the Bowery as a whole, they’re not considering it as a place,” said Kerri Culhane, an architectural historian and the associate director of Two Bridges.

After years of seeking, and failing, to get city landmark status for even small, largely intact, stretches of the Bowery, the groups have recently intensified efforts to convince City Planning to create an overlay zoning district that would cap building height on the eastern side of the street to 85 feet, reflecting zoning restrictions that are already in place on the western side of the street. “To do justice to the Bowery, you really need to do justice to both sides of the street,” said Ms. Culhane.

The effort has attracted supporters among local businesses, restaurateurs, museums and even Martin Scorsese, who last week penned a letter to planning chair Amanda Burden. The filmmaker wrote that “having grown up on Elizabeth Street, the neighborhood and residents of the Bowery became clear catalyst for turning me into a storyteller. Whether it’s Mean Streets or Gangs of New York, the influence of the Bowery—the grittiness, the ambiance, the vivid atmosphere is apparent.”

A zoning change won’t do much to preserve the grittiness, we’re afraid, but it could protect a lot of the old buildings. Preserving a neighborhood’s architectural character isn’t quite the same as preserving the underlying emotional character—but the two are entwined. And over time the Bowery has proved, if nothing else, to be both protean and resilient.

“We’re talking about one of the oldest stretches of America before it was America. It was a highway for humans that goes back no one knows how long. This is where the mores and culture of America were established, the cradle of pop culture,” former Landmarks Commissioner Kent Barwick told the Observer. “There’s probably no stretch of New York that has more history per inch than the Bowery.”

Indeed, if the Bowery has been anything, it has been everything: a Native American footpath, a Dutch farm road, the place where George Washington stopped for a drink before watching British troops leave the waterfront, and where Abraham Lincoln gave the anti-slavery speech that got him the Republican presidential nomination. It has been home to both Astors and drug addicts, a place of circuses, movies and brothels. It has nurtured tap dance, vaudeville, Yiddish theater, Abstract Expressionism, Irving Berlin, Patti Smith and punk rock and now ... well, no one really knows what comes next. Just that the thoroughfare should remain as central to the New York experience as it has always been.

“It was always so quintessentially New York—a little bit naughty, the underside of the city, the underside is always the real city,” reflected Mr. Barwick. “The Bowery still has that sense of being the real New York, something special, the place where talent is more important than connections. But it’s on life support.”

kvelsey@observer.com

Zapata and Vergara. (Eugene Mim/Patrick McMullan)

“I turned the penthouse of The Bowery in to my studio ... I have a studios in Paris and L.A., so I go back and forth,” Domingo Zapata said as he moved intimately among a crowd of familiar faces. If upstairs was the studio, then the second floor of the hotel was his gallery space. Large canvases of his art, all paying homage to American pop culture, were on display—works exhibiting a distinctly playful nature, exemplified best by a painting of Superman flashing a peace sign, proclaiming he was available for hire.

“I love sharing my work with my friends. It's intense, but good.”

With friends like his—a bevy of beautiful muses including the likes of Kim Kardashian, Eva Longoria, Lindsay Lohan and attendee Sofia Vergara—he's not exactly lacking in inspiration. 

Ms. Vergara, wearing a faint-inducing mini-dress, shared the red carpet with Mr. Zapata, without her new fiancé Nick Loeb. She did manage to find time to take a few (more) photos with Mr. Zapata, though. The room abuzz, packed with buyers and boozers alike, we squeezed through the wall-to-wall crowd, taking in Mr. Zapata's whimsical interpretations.

“I wanted to do a tribute to the Bowery and East Village and Manhattan and the graffiti that you see around the city. I also love movies and classics like Superman and Pink Panther. These represent all that coming together.” Keen to express his broader artistic philosophy, he continued, “there is not such a thing as good art or bad—there are 50,000 artists in New York City. It's not about the quality, its about the creation; without creation we don’t even exist.”

Outside, a beautiful fall evening beckoned, with gorgeous women and cocktails abounding. Was tonight to be all work?

“We are going to a place called Provocateur in the Meatpacking District—it’s going to be a long night.”

Was this a common occurrence?

“There are 12- to 14-hour days where I'm painting. I have a lot of projects coming up; for instance, I’m working on paintings for the lobby of the World Trade Center.”

We left the artist to his own—which was cozily in the middle of a ever-growing crowd holding out hands to shake his—wondering if we were worthy of his canvas.