One of the key films of the American counterculture, but its concerns remain universal and fundamentally Western Philosophical (whilst parading much that is Eastern Philosophical). Julius Orlovsky. One of the most important figures in all cinema. He directly confronts us not only w/ the question of what it means to appear (or not appear whilst appearing) before the camera, but what it means to appear at all.
Robert Frank is an icon of art photography. I recommend his book 'The Americans'. He is also an unconventional and experimental filmmaker. Part documentary, part fiction, this movie has an amazing assortment of literary greats. It looks a little bit like a mess, but if you're interested in that period of history and a wide assortment of characters, look no further.