Followed by New Jersey, no surprise there.. The 50 most miserable cities in America The 50 most miserable cities in America James Pasley Angela Wang Sep 28, 2019, 10:00 AM The east side of Detroit. Charles Ommanney / Getty The most miserable city in the US is Gary, Indiana. The state with the most miserable cities is California, with 10. New Jersey is close behind, with nine, and Florida comes in third, with six. These cities have things in common - few opportunities, devastation from natural disasters, high crime and addiction rates, and often many abandoned houses. .