@hce1 , welcome to the movie club within the audio club!
Gus Van Zant: Drugstore Cowboys and Good Will Hunting were mentioned above, and I second those recs. Also excellent: To Die For (written by Buck Henry, with stunning performances by Nicole Kidman, Joachim Phoenix, Matt Dillon), Paranoid Park, Elephant, Milk, Finding Forrester
Although I don't pay enough attention to directorial credits I like some of your movie choices and there are a couple I am not familiar with (Paranoid Park, Elephant) but I'll do some googling and if they look interesting enough, I'll check 'on demand.' I remember being mesmerized by Drugstore Cowboys not only because I like Matt Dillon, but also because, in my misguided youth, a few years before it came out, I had known someone who acted as a middleman for someone else (who I never met) who specialized in the Drugstore Cowboy thing. Although I think it was a short career.
And coincidentally, quite recently I watched The Trials Of Pamela Smart.

