As of 1884, at least. This poster reminded me of a time back in the ’90s when I was standing at the southern end of City Hall Park in New York. Standing in one spot I could see four buildings that were, at the time they went up, the tallest buildings in the world; along with one more that was the tallest in New York.
Trinity Church
13-21 Park Row
WTC
Woolworth Building
Chrysler Building
Thanks to Kottke for finding this one.