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While this question mostly spans before 1960, you could answer this question with the various beautiful buildings now lost, for example, the Singer Building, old Pennsylvania Station, the various Gilded Age mansions, very recently the Hotel Pennsylvania, or the old industries or parts of the culture, the working class Bowery communities, Little Syria on the Lower West Side or the ‘Toidy-Toid street’ accent you’ve heard many stars from the 1930’s speak with, or musical scenes such as the Big Bands of the 30’s and 40’s, the smaller, underground, but very innovative Jazz groups of the 40’s and 50’s or even the Greenwich folk scene of the late 50’s to 60’s.