Manhattan is known for its iconic skyline, brimming with skyscrapers, high rises, and some of the most impressive architecture in the world. But it wasn’t always that way; it took hundreds of years for New York City to become the structurally diverse, world-famous city that it is today.

Some of the first skyscrapers to shape the Manhattan skyline included the Metropolitan Life Insurance Company Tower (built in 1909) and the Woolworth Building (built in 1913). The buildings stand at 700 and 792 feet respectively, and at the time, they towered above earlier structures such as the famous Flatiron Building which stands only 285 feet tall. Over the next 100 years, the skyline continued to grow and evolve, with many different architectural styles and influences from different time periods still visible today. This poster, created by Liberty Cruise NYC, gives us a glimpse of what the Manhattan skyline looked like every two decades from 1920 to 2000 and what it will look like by 2020.

The skyline has grown remarkably taller over the past hundred years. Manhattan’s tallest building in 1920, the Woolworth Building, at 792 feet, is nearly a thousand feet shorter than the highest skyscraper in 2020, One World Trade Center, at 1,776 feet. One World Trade Center remains the tallest building in the United States.

Today’s Manhattan skyline features many architectural styles, including the Neoclassical 14 Wall Street, the Art Deco Chrysler Building, the Beaux-Arts Manhattan Municipal Building, the Brutalist AT&T Long Lines Building, and so much more.

1920

1940

1960

1980

2000

2020