History Of New York’s Fascination With The Flatiron Building

New York City is filled with famous landmarks, but few buildings capture the imagination quite like the Flatiron Building. Standing at the dramatic intersection of Fifth Avenue, Broadway, and 23rd Street, the Flatiron Building has fascinated New Yorkers, tourists, photographers, architects, and filmmakers for more than a century. Its triangular shape, steel-frame design, and almost theatrical presence along Madison Square Park have made it one of the most recognizable buildings in New York City history.

Flatiron Building in New York City

Photo: Brian Kachejian 2018

Most tourists who travel to New York City plan their visits around the Empire State Building, the Statue of Liberty, the World Trade Center, St. Patrick’s Cathedral, and Rockefeller Center. Obviously, those are exciting places to visit if you have never been to New York City. However, many tourists somehow never make it to the Flatiron District. The out-of-towners do not know what they are missing.

New York’s Flatiron Building has always been one of the most fascinating buildings to ever line the New York skyline. It has also become one of the most photographed buildings in the city’s history among New Yorkers. The fascination that New Yorkers have had with the building over the past century is simple. There has never been another building that has come close to resembling the architecture of New York’s Flatiron Building.

Visiting The Flatiron Building

Visiting the Flatiron Building is, for the most part, an exterior experience. The building is owned by private businesses, and the only views one may have from the inside are in a small hallway lined with photographs and the building’s history. Most visitors will not get past the initial hallway, as security stops anyone from entering deeper into the building. One day, Alice, we will find a way.

Flatiron Building interior hallway

Flatiron Building Interior. Photo: Brian Kachejian 2018

History Of The Flatiron Building

There is a misconception that the Flatiron Building was named for its shape. The fact is that the section of New York City in which the Flatiron Building was built was already nicknamed the Flat Iron because of the triangular intersection of Fifth Avenue, Broadway, and 22nd and 23rd Streets.

In 1867, a wealthy New York banker, Amos Eno, purchased the triangular plot of land where the Flatiron Building would eventually be built. “Eno’s Corner,” “Eno’s Triangle,” and the “Flat Iron” were often used to describe the parcel of land Amos Eno had purchased.

In 1899, after Amos Eno had passed away, his son sold the land to Mott and Samuel Newhouse for just over $800,000. Two years later, in a shining example of the power of New York City real estate values, the Newhouses sold the same plot of land they had purchased for eight hundred thousand dollars to the Cumberland Realty Company for two million dollars. Only thirty-three years earlier, Amos Eno had bought that same land for just thirty thousand dollars.

The Fuller Company And Daniel Burnham

The Cumberland Realty Company was connected with the Fuller Company. Harry S. Black, CEO of the Fuller Company, hired Chicago’s Daniel Burnham to design the skyscraper he intended to build on the triangular parcel of land his Cumberland Realty Company had purchased. The building was supposed to be named the Fuller Building in reference to the general contracting Fuller Company. However, the building’s location on the Flatiron parcel of land and its triangular shape led it to inherit the name Flatiron Building.

The brand-new skyscraper on 23rd Street was not exactly met with open arms by everyone. In Keith Jackson’s brilliant book Empire City, the noted historian and professor noted that early-twentieth-century writer Henry James argued that buildings like the Flatiron were destroying the aura of the city. James described buildings like the Flatiron as not works of art but rather “giants of the mere market and part of the steel-souled machine room.” Harry James had no idea of the transformation that awaited New York’s Acropolis over the next century.

Historic Flatiron Building photograph from Broadway and 22nd Street

Photo: Art and Picture Collection, The New York Public Library. “Flatiron Building from Broadway and 22nd street, with eight stories in terra cotta.” New York Public Library Digital Collections. Accessed February 26, 2018. http://digitalcollections.nypl.org/items/510d47e0-ce75-a3d9-e040-e00a18064a99

Flatiron Building exterior

Photo: Malinda Kachejian 2018

Why The Flatiron Building Still Stands Apart

Henry James may not have realized how extensively the skyscraper boom of the early twentieth century would develop over the next one hundred years, but he did recognize the transformation of the city’s landscape in the shadows of the new model of building design. While that transformation continued consistently, the design of the Flatiron Building would stand alone to the present day.

Simply stated, there is no other building in New York City that looks anything like the Flatiron Building. The Flatiron Building’s design, centered on that small triangular patch of land at Broadway and Fifth Avenue, has made it one of the most fascinating buildings ever erected in New York City.

There are times when walking down Fifth Avenue, one takes a look at the Flatiron Building with the same astonishment as seeing the Roman Colosseum standing in the middle of the modern-day streets of Rome. In one breath, it seems so out of place, as if it just appeared out of thin air in some sort of Twilight Zone episode reproduction. On the other hand, it feels like a part of New York City that has always belonged.

The way the sun casts the shadows of other buildings upon its flat side is a mesmerizing sight. On cloudy days, it looms above Madison Square Park with its pointed front edge staring down at the park like a ship breaking the shoreline. Its architecture, just in its shape alone, is daunting as it stands starkly at one of the most exciting intersections in New York City.

Flatiron Building from Fifth Avenue

Photo: Brian Kachejian 2018

The Flatiron Building In Movies, Television, And Photography

New Yorkers’ fascination with the Flatiron Building stems from the need to capture its spirit on film and in print and digital media. The Flatiron Building has a long history of being utilized in television shows and on the silver screen. Fans of the legendary Spider-Man movie series have been treated to the Flatiron Building’s use as the host of the fictional Daily Bugle newspaper. The iconic television series Friends often utilized shots of the Flatiron Building in transition scenes. From film to print, the Flatiron Building’s majestic architecture has challenged artists to interpret its aura in creative ways.

Flatiron Building up close from the front

Photo: Brian Kachejian 2018

Flatiron Building corner view

Photo: Brian Kachejian 2018

Flatiron Building side view

Photo: Brian Kachejian 2018

Flatiron Building Broadway entrance

Photo: Brian Kachejian 2018

Flatiron Building street view

Photo: Brian Kachejian 2018

Flatiron Building facade

Photo: Brian Kachejian 2018

Flatiron Building sign

Photo: Brian Kachejian 2018

Historic Flatiron Building illustration

More New York City Landmark Stories

If you enjoy reading about New York City landmarks, take a look at our features on Grand Central Terminal, St. Patrick’s Cathedral, the Second Avenue Subway, and Eataly in the Flatiron District.

Source: Jackson, K.T., Dunbar, D.S.: Empire City: New York Through the Centuries. Columbia University Press, New York, 2005. p. 477.

Article updated June 27, 2026.

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