Once New York City's most famous skyscraper, the Fuller Building, will be forever known as the Flatiron Building because its triangular shape, only six feet wide at its rounded narrow end, resembles a flat iron.
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 Although it wasn't the city's first skyscraper, first steel-skeleton building or ever the worlds tallest building — all things that are traditionally associated with the Flatiron Building — it was the first building to become a romantic symbol of New York.
It was built at a time when there were so few tall buildings in New York that you could see the Flatiron Building from Central Park.
A very popular photographic subject—Edward Steichen's is famous— the steel-framed terra-cotta and limestone-clad 21 floor skyscraper was featured in the motion pictures Spider-Man 1 and 2 as the office of the newspaper Daily Bugle.
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 The intersections formed by Broadway's diagonal path across the otherwise geometric grid of Midtown Manhattan streets forms a number of interesting intersections, most notably Times Square where it crosses Seventh Avenue.
As Broadway crosses Fifth Avenue it forms a small triangular patch of ground between 23rd and 22nd streets that has become known around the world as the location of the appropriately shaped Flatiron Building.
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 Local lore, and many historical postcards, have it that the juxtaposition of the angled building and Madison Square Park across Broadway generated a wind-tunnel effect that caused women's dresses to flair exposing their ankles to men who gathered on 23rd Street for the show. The slang expression "23 skidoo" supposedly originated when the police used it to disperse the voyeurs.
The Flatiron Building is one of the hop-on, hop-off stops on the popular Downtown Loop of the classic double-decker bus tours. There are a number of good restaurants in the neighborhood.
 One of the earliest buildings—and possibly the tallest in New York at the time—to utilize a steel frame with non-load-bearing facades, the Flatiron was meant to resemble a classical column with a protruding and ornamented base and top. The Flatiron's facade is richly detailed rusticated limestone with gently undulating bays to break the sense of sheer wall. A continuous, triangular cornice runs around the building.
The design was influenced by architectural trends introduced at the 1893 World's Columbian Exposition in Chicago and combines elements of French and Italian Renaissance architecture.
Probably the best and liveliest of Chicago Architect Daniel Burnham's designs, the building was meant to be named the Fuller Building because it was originally occupied by the Fuller Construction Company. A 40 story building at Madison and 57th Street now bears the Fuller Construction Company name.
Daniel Burnhham had been known as one of Chicago's great modernists, but after the death of his partner in their firm Burnham and Root he became much more conservative and stodgy. The Flatiron Building's unusual shape and extreme height, for its day, gave New Yorkers concern that it would fall down so for a while it was known as "Burnham's Folly."
Madison Square Park
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Madison Square Park anchors the southern end of Madison Avenue. It was officially designed as a public space in 1847 and has the distinction of being surrounded with historic buildings. The rules of baseball were officially set down by Alexander J. Cartwright, a 25-year-old volunteer fireman, and the game as it is now known was first played in the vicinity of Madison Square. The original Madison Square Gardens was located here when the famous Jack Dempsey fights took place.
The right arm and torch of the Statue of Liberty were on display in the park between 1876 and 1882 in order to raise money for the design and construction of a base for the statue. Madison Square Park had suffered many years of neglect but was restored and rededicated in 2001.
 The MetLife Tower — also shown at the very left in the photo above, taken from the Empire State Building, and at the very right of another photo from the same location shown below — was built in 1909 and was the tallest building in the world until it was eclipsed by the Woolworth Building in 1913.
Built to serve as the Metropolitan Life Insurance Company headquarters, the MetLife Tower was modeled on the campanile at St. Mark's Square in Venice. The tower has recently been restored — a process that took several years because of its historic stature and public visibility.
This follows an aggressive remodeling in the 1960's that stripped the building of its ornamental details. Paul Goldberger in his Guide to the Architecture of Manhattan, "The City Observed," comments about that earlier remodeling that the base structures were entirely rebuilt at the same time and even though the removal of the ornamentation simplified the tower enough of the building's integrity remains.
 The massive art deco North Building next to the MetLife Tower was originally planned to be 100 stories tall to return the title of 'worlds tallest' back to the Metropolitan Life Insurance Company, but the Great Depression halted construction at 29 floors in 1932.
The six story gilt pyramidal tower of the New York Life Insurance Company building at 51 Madison Avenue seems a little small for the building but never-the-less provides a distinctive golden glow and silhouette on the New York skyline. The building was designed by architect Cass Gilbert — who also designed the Woolworth Building — and constructed in 1928 on the site of the original Madison Square Gardens.
The 40 story building (including the six-story crown) has an Italian Renaissance base and features details including marble surrounds at the entrance, window spandrels and gargoyles at the roof line.
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