4. 77 Water Street – 1970
77 Water Street is among the most playful buildings designed by Emery Roth and Sons. On 77 Water, the firm collaborated with developer Melvyn Kaufman, a favorite of Richard Roth Jr. Kaufman liked to infuse his buildings with whimsical flourishes, and 77 Water in the Financial District is a prime example of his quirky flare.
At the entrance plaza to the 26-story office building, you’ll find a candy store that looks like it was transported from the old wild west. On the building’s roof, there is a full-size model of a World War I-era warplane. The stainless steel model even has its own Astroturf runway complete with landing lights. Why put an installation like this on the roof? Because people in the taller buildings that surround 77 Water Street could see it as they look out their windows.