Chrysler Building | Manhattan, NY

We won’t argue if you want to call this glimmering pinnacle of Art Deco architecture NYC’s most eye-popping skyscraper. Triangle-shaped windows in its crown are lined with lights, creating a beautiful effect come nighttime. Oozing a moneyed sophistication oft identified with old New York, the structure pays homage to its namesake with giant eagles (replicas of ones added to Chrysler automobiles in the 1920s) in lieu of traditional gargoyles and a brickwork relief sculpture of racing cars, complete with chrome hubcaps. During the famed three-way race to construct Manhattan’s tallest building, the Chrysler added a needle-sharp stainless-steel spire to best 40 Wall Street—but was outdone shortly after its completion in 1930 by the Empire State Building.