The Chrysler Building was commissioned by the car company founder Walter P. Chrysler, who called it “a monument to me.” Constructed between 1928 and 1930, it rose to a staggering 1,046 feet.

RUTH COLP-HABER: The Chrysler Building is considered one of the true grandes dames of New York City real estate. That being said, at this point in time, it's facing a real crossroads.

But the Chrysler Building could also be dwarfed in the next decade by 175 Park Avenue — aka Project Commodore — that could rise to 1,581 feet on the site of the Grand Hyatt Hotel right across ...