Iconic Buildings

An extensive collection of vintage pictures of some of New York’s (and the world’s) most iconic buildings including the Empire State, Chrysler, Woolworth and Flatiron buildings, the Times Tower, Grand Central and Pennsylvania Stations, the New York Public Library, and more.

Flatiron Building, 1907

Flatiron Building, 1907
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East River Skyline, c. 1955

East River Skyline, c. 1955

The Manhattan Skyline viewed from Roosevelt Island in 1955 looks strikingly familiar to a contemporary viewer. The art deco spires of the Chrysler Building and the Empire State Building spear the sky, and the cigarette-box-shaped United Nations waits impassively for the better world its construction was supposed to help usher in. But the majestic giants of the second half of the Twentieth Century are conspicuously absent. The Citigroup Center, the Bear Stearns Building, the MetLife Building, and many others have yet to replace their smaller, forgotten predecessors.

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East 42nd Street and Second Avenue, c. 1932

East 42nd Street and Second Avenue, c. 1932

Looking west along Forty-Second Street from Second Avenue, you can see the Third Avenue Elevated Line and, beyond it, the Chrysler Building. The street is quiet, with only a few cars parked at the curb and a few pedestrians in winter coats walking briskly past the City Coffee Pot. The newly-constructed Daily News Building is on the left, just beyond the Coffee Pot.

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Main Entrance of Grand Central Terminal, 1914

Main Entrance of Grand Central Station, 1914

Seen from this angle Grand Central Terminal is indeed the cathedral of transportation it was intended to be. This photo was taken not long after GCT entirely replaced Grand Central Station, which was torn down in phases between 1903 and 1913. The perspective here is approximately eye-level with Mercury, who anchors the statue "Transportation," which faces south at East 42nd Street and Park Avenue.

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The Empire State Building Under Construction, 1930

The Empire State Building Under Construction, 1930

At the time of this photo, the Empire State Building was just surpassing the Chrysler Building as the tallest in the world. Completed in 1931, the Empire State Building was for forty years the pinnacle of skyscraper architecture. The portion that is still being constructed in this photo is not the familiar antenna that we know today, but what was intended to be a mooring mast and dock for airships. The first few attempts proved the impracticality of this idea. Imagine being a passenger disembarking across a gangplank 102 stories above Fifth Avenue.

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Central Park near East 62nd Street and Fifth Avenue, 1940

Central Park near East 62nd Street and Fifth Avenue, 1940

It's a beautiful summer day in 1940, and from where you stand in Central Park, you can see two of the most luxurious hotels in the world, the Sherry Netherland and the Plaza. The Plaza is perhaps the better known of the two, but sadly will eventually become a luxurious residence. The Sherry Netherland, however, will remain the pinnacle of New York City luxury for some time to come.

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Flatiron Building, 1902

Flatiron Building, 1902

A view south towards the Flatiron Building at the intersection of Fifth Avenue, Broadway, and 23rd Street.  This portrait was taken shortly after the completion of the building, at which time it was one of the tallest buildings in New York City.  The strong winds along with the downdrafts created by the building often caused women's skirts to be blown up.  The phrase, "23 Skidoo" purportedly comes from what policemen would shout at the men who loitered in the area awaiting the show.

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Construction of the Times Tower, 1904

Construction of the Times Tower, 1904

A view south at Broadway and West 44th Street toward the construction of the Times Tower.  At the time of its construction it was the second tallest skyscraper in New York City.  When its new headquarters opened on January 1, 1905, the New York Times celebrated with a fireworks display at midnight.  The tradition of celebrating the New Year in Times Square continues to this day.

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Woolworth Building from the Clouds, c. 1920

Woolworth Building from the Clouds, c. 1920

In this aerial view of Lower Manhattan, the top of the Woolworth Building peeks through the clouds.  At 792 feet, the Woolworth Building, designed by architect Gilbert Cass, overtook the Metropolitan Life Tower as the world's tallest building when it opened in 1913.  It is still one of the twenty tallest in New York City.

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Construction of Streetcar Tracks, 1900

Construction of Streetcar Tracks, 1900
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