New York City has suffered widespread power outage three times since WWII, most recently in 2003, when it went dark with the rest of the northeast, including parts of Canada.
The blackout of 1977 was perhaps the most iconic, however, since unlike 2003 or 1965, the outage was confined to the city and lasted through the night and into the following morning. According to Wikipedia: "In all, 1,616 stores were damaged in looting and rioting. A total of 1,037 fires were responded to, including 14 multiple-alarm fires. In the largest mass arrest in city history, 3,776 people were arrested. Many had to be stuffed into overcrowded cells, precinct basements and other makeshift holding pens. A congressional study estimated that the cost of damages amounted to a little over $300 million."