New York Life Building

The New York Life Building dominates the block between Madison Avenue and Park Avenue South with a presence that feels more like a towering cathedral than a corporate office. Architect Cass Gilbert designed this neo-Gothic skyscraper in the late nineteen-twenties, drawing direct inspiration from the medieval spires of Salisbury Cathedral in England. You can see his signature style in the limestone facade, which incorporates seventy-two grotesque stone carvings that peer down at the busy streets below. The building is perhaps best known for its octagonal roof, which is covered in over twenty-five thousand gold-leafed tiles that shimmer against the city skyline, signaling the financial prestige of the insurance company that still calls this place home.