The Lipstick Building Of NYC: From Eyesore To Icon
Photo by The Empire City Wire
A New Building
When the Lipstick Building first opened its doors in 1986 at 885 Third Avenue, it was met with a mix of confusion, criticism, and outright mockery. Designed by Philip Johnson and John Burgee, the 34-story elliptical tower—with its burgundy granite and stainless steel cladding—looked nothing like the boxy, angular skyscrapers that dominated the Manhattan skyline. Its rounded, tiered form earned it the nickname “The Lipstick Building,” a comparison that, while playful, wasn’t always flattering.
Critics at the time didn’t hold back. The building was labeled “silly,” “cartoonish,” and “out of place.” The NY Post even listed it in an article on 10 Buildings We Love To Hate. In a city where sleek minimalism was considered the height of architectural sophistication, the Lipstick Building’s curves and color palette felt jarringly different. It was architecture with personality in a city that, at the time, seemed to prefer stoicism.
Source: The U.S. Department Of Justice. Public Domain
The Madoff Scandal
The Lipstick Building’s distinctive architecture isn’t its only claim to fame. For years, it was also the headquarters of Bernie Madoff, whose multi-billion-dollar Ponzi scheme became one of the most infamous financial scandals in American history. Madoff operated out of the 17th floor, a relatively nondescript office space tucked inside one of the city’s most visually recognizable buildings.
In the aftermath of the scandal, the Lipstick Building became a symbol of financial deception as much as architectural quirk. Media crews camped outside its entrance during Madoff’s arrest and trial, and images of the building became closely associated with the scandal. For a time, the building’s elliptical curves were shadowed by the infamy of what had taken place inside.
But, like many things in New York, the story evolved. The building wasn’t torn down or shunned—it endured. And today, the association with Madoff has faded into the broader context of the building’s history. If anything, it added another layer of New York mythos to the structure. In a city where architectural icons are often tied to cultural moments—some glamorous, some sordid—the Lipstick Building simply joined the ranks of structures that have seen too much to be forgotten.
Photo by The Empire City Wire
Time Reshapes Perspective
Today, the Lipstick Building has settled into its role as a recognizable, almost beloved, fixture of Midtown. Its bold shape, once the subject of ridicule, now reads as a refreshing contrast to the glass-and-steel anonymity of newer developments. In fact, some New Yorkers argue it’s aged better than the ultra-thin, ultra-tall “pencil towers” now piercing the skyline. Those new additions, designed with wealth and height as primary virtues, have drawn sharp criticism for their shadows, their empty investment-unit floors, and their overwhelming presence. Compared to these monoliths, the Lipstick Building suddenly doesn’t seem so outrageous.
There’s also something comforting in its distinctiveness. While other buildings blend into a sea of reflective façades, the Lipstick Building’s curved exterior still draws the eye. Its form is confident, even playful—a reminder that architecture doesn’t always have to take itself so seriously.
One of the most underrated features of the Lipstick Building is its elegant colonnade at street level. The tall, slender columns that encircle the base create a sense of rhythm and openness, offering a graceful transition between the sidewalk and the structure’s dramatic elliptical form above. These columns not only add to the building’s sculptural quality, but they also give it a surprising lightness—inviting pedestrians in rather than walling them off. In a city where many skyscrapers meet the street with hard edges and blank walls, the Lipstick Building’s columned base feels both intentional and humane.
A Fixture In The Skyline
In a city that reinvents itself block by block, the Lipstick Building stands as proof that not every controversial structure is doomed to be torn down or forgotten. Sometimes, the things we think are ugly just need time to grow into their place—and into our collective affection.
Today, the Lipstick Building is still standing, still gleaming, and still undeniably itself. And in a skyline increasingly dominated by sameness, that’s no small feat.
