Hacker Cinema
Hobo
1992 · Film · documentary · 90 min
Directed by John T. Davis
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. Along the way, the pair meet with several other men living life on the margins.
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Another, more recently, is the documentary Hobo; riding the rails in the 1990s:
https://m.imdb.com/title/tt1646104/