No idea about prose, but in terms of fiction, Death of a Salesman is the obvious one, I guess. Also, Rise of Silas Lapham, maybe?
I'll be honest with you, I don't like to read books about man and life and business all in a single work. I took a few American literature courses, but none dealt with all those themes.
For something completely different, have you ever read Slaughterhouse-Five?