I recently picked up a really great documentary film called Musician from a film series called Work. It follows Chicago saxophonist Ken Vandermark. Ken, for those that know his music, is a inspiring figure in avant garde music. The thing that is really interesting is that this film doesn't really focus on Ken music as much as the lifestyle of a working musician. Booking gigs, travel, balancing family life, load in and out, hotels, etc, etc. All the **** that all of us making a go of this musician lifestyle have to deal with. I highly recommend it.
http://www.workseries.com/musician/