I would like to recommend two books, one a hugh volume on the history of New York City, starting with the colonization by the Dutch in the 16th century, l7th century, 18th century and 19th century New York City. It is called Gotham and is over 1,000 pages but if you were born in New York City as I was ( actually Brooklyn) you will find it amazing. The other volume is much smaller and very entertaining. It's called "Low Life", by Luc Sante, and it is exactly what it says, the low life of l9th century New York City, gangs, crooked police, crooked politicians, political bosses, houses of ill repute, opium dens etc. If "Gotham" appears overwhelming do read "Low Life". You will not regret it.