For 50 years, the 281-foot-high steeple of Trinity Church was the tallest structure in Manhattan. Captain William Kidd, later a notorious pirate, lent tackle from his ship to hoist stones to build the church.

Built in 1763, this sugarhouse was the tallest in the area. By the 1890s it was dwarfed by its taller neighbors and had suffered obvious neglect when it caught the attention of photographer Robert Bracklow.

The 1872 Bennett Building's key feature is its facade: it is the tallest structure in the world with an entirely cast-iron facade.

Another great cast-iron wonder was located at 853 Broadway. During its construction in 1873, it was hailed as an early skyscraper.

Completed in 1875, the Tribune Building was the tallest office building in the city, with a clock tower stretching it to 260 feet.

At the time of her dedication, the Statue of Liberty was the tallest structure in New York at 305 feet. Today it remains a potent symbol of New York and the nation.

The ten-story Hotel Margaret laid claim to being the tallest building in Brooklyn 1889, the year it was built. The tower overlooked the New York Harbor and Manhattan from Columbia Heights and Orange Street in the Brooklyn Heights neighborhood.

When completed in 1890, the World Building was the tallest in the city, and the tallest office building in the world.

A brief contender: the 16-story Hotel Manhattan was completed in 1896 at a whopping 250 feet tall.

This 30-story Park Row Building was the tallest office building in the world from the time of its completion in 1896.

The Metropolitan Life Tower was the tallest building in New York in 1905.

The Hotel Belmont was the tallest hotel in the world when completed in 1906.

According to legend, Jarmulowsky added the capital to the top of the building so that it would be the tallest in the neighborhood when built in 1912.

This 539-foot-high tower was the tallest bank building in the world when it was completed in 1912. The tower utilized the latest in building technology, including one of the first cofferdam foundation systems in the city,

The Woolworth Building reigned as the world's tallest skyscraper from its completion in 1913 until William Van Alen's Chrysler Building surpassed it in 1929.

Though overshadowed by newcomers, the Ritz Tower was once the world's tallest residential building when completed in 1927.

Also completed in 1927, the Sherry-Netherland took the title from the Ritz Tower Hotel as the "the tallest apartment building in the world... \[with] 125 apartments." (The New York Times)

The Chrysler Building only remained the world's tallest for less than a year, eclipsed by the Empire State Building in 1931. Though, it's still the world's tallest steel-supported brick building.

The Empire State Building's antenna helped to make it the tallest building in the world from 1931-1972.

When Beth Israel’s new, 500-bed facility opened in 1929, the thirteen-story building was the world’s tallest hospital.

Riverside Church is the tallest church building in the United States. It was completed in 1930.

Brooklyn's Williamsburgh Savings Bank was the tallest structure between Manhattan and Paris. All 512 feet were built between 1927 and 1929.

The Waldorf Astoria combined a transient hotel and separate residential tower into a 625-foot-high skyscraper. It was completed in 1931 and held the title of the largest and tallest hotel in the world.

At the time of completion, 70 Pine Street was the tallest structure in lower Manhattan and the third tallest structure in the world, topping off at 952 feet.

The Twin Towers were initially designed to be 80-90 stories. However, at 110 stories tall they were the world's largest man-made structures in the world, following a suggestion said to have originated with the Port Authority's public relations staff.