When I had to choose a meeting place for a drink this week I focused on something that would match the Henry James novel I'm reading. The action of the novel takes place in 1840s New York and I was pleased to suggest to my friends that we meet in a building from the Henry James era.
The 1820's structure shown below was built by a black war veteran who ran a tobacco importing business from the first floor. It is now the home of the Ear Inn, so named by some fellows who wanted to avoid the tax fee of registering a new business name and so simply painted over part of the letter B in the neon BAR sign out front in the 1970s.
The entire structure was condemned in 1906 but somehow it all survived and I'm meeting two friends for a "goodbye to New York" drink at the Ear Inn on the first floor this week before moving to Madison, Wisconsin. Look in the photo at how the poor building cowers amidst the new construction (it's the smaller building, behind the tree).
How great to have a landmark place to satisfy a dual historical appetite for both gritty Koch Era / Taxi Driver era NYC and also Henry James era NYC at the same time!
There is more info on the Wikipedia page for the James Brown House.