8. Tudor City
Tudor City on East 42nd Street, which was the first residential skyscraper complex in the world, is considered one of the failures of urban planning. When it was completed in 1932, the architects turned their backs on the waterfront and built facing in instead of out. The resulting complex doesn’t take advantage of the spectacular views onto the East River. However, the Tudor City Bridge is a great vantage point for seeing Manhattanhenge, the phenomenon when the setting sun aligns perfectly with Manhattan’s grid.