On the off-night before the playoffs started, we saw a really good movie: "Everyday People". The story takes place at an old-fashioned Jewish deli, whose future is in doubt as its Brooklyn neighbourhood is gentrified. (Those who know the area will recognize a place like Juniors and the downtown neighbourhood around Borough Hall.) We meet some of the people who work there, the owner and the developer - a glimpse behind the headline when a local institution closes.
The filmmaker, Jim Mackay, is known for working with largely unknown actors, and holding improvisation workshops to develop the script from people's experiences. The results are characters with subtlety and depth, instead of the stock-character types often seen in ensemble scripts. Mackay presents questions, but he doesn't point the viewer to easy answers.
Mackay's previous film, "Our Song", was about a marching band in a low-income Brooklyn high school. It was excellent - and so was "Everyday People". Here's a story about Mackay and the making of Everyday People, and an interview with him after the release of Our Song.
Two poignant and subtle urban movies, worth adding to your list.