Hobo (1992)

Irish director John T Davis stashes a camera in his bedroll, catches out, and rides the rails from Minneapolis to Seattle with Beargrease, a part-time hobo and full time philosopher, who narrates their way through the incredible scenery of the Northwest and gives us his views on life, liberty, and the pursuit of happiness. The pair meet up several other men living life on the margins: in particular a scene in which Duffy - an ex-corporate executive now living under a bridge in Spokane & collecting cans - describes how he got there is riveting.