Water Street used to be infamous for being very winding and not having a properly organized street wall. Even buildings made of stone would often jut out into the street at various angles and not line up with one another. It was ridiculed by the British (and others, I'm sure), and we grew embarrassed about it. There were lots of articles in the papers back then about what a shame it was to have such a haphazard, disorganized city.
At every opportunity, including after the Great Fire of 1846, and especially after the Great Fire 1892, we tried to widen and straighten streets.
Water Street, pre-1892:
It's too bad. We would've had lots of lovely little nooks and crannies for sidewalk cafes like small-town Europe.