This will be a cult classic one day

I couldn't agree more. I've watched this thing like 4 times now. It's emotional without being sentimental. When gandolfini runs out to give Doug some cash and the there's that beautiful shot of him standing under the street sign? I got choked up. I also like how Chase also manages to have all the characters talk like real people, but the dialogue is still insightful and thought provoking. Sure it doesn't have much of a plot, but in my opinion it doesn't need one. Awesome, funny, and beautiful movie.

I've seen this 3 times now and I think it's something of a great film (despite the overly meta- final shot/scene, which just doesn't work for me). But you probably have to be familiar with, or into, Chase's aesthetic and worldview as established on The Sopranos, to really appreciate it. It's a rare 60s period piece that doesn't idealize, mythologize or sanitize the reality. It just seems, as you said, real, like any other time in history. The film is also aesthetically pretty great, filled with the kind of intelligent, funny, quick editing choices and lush, dark, autumnal, very natural-looking images that marked the later seasons of The Sopranos. It's a film also full of great sardonic Chase-ian humor, and just as much melancholy and regret and disillusionment. Chase captures the reality of most people, or at least a certain type of people, with such hilarious accuracy -- the narcissism, the absurd repeated pronouncements and cries for attention, the jealousy and anger and petty squabbling, and the way people use and mangle language as they like. He's a great observer of human behavior, and I think if he turns out another film at least as good as this, we could say he's a great filmmaker, too. The Sopranos was certainly the greatest TV series ever (or, at worst, in the top 2 or 3), but Chase has now proven that he's just as insightful and bracing in film-form. Too bad that this film lost so much money, though. I read it made 600k on a 20 mil budget -- ouch.