My grandfather was a hobo. As a teenager he decided to hop a train and live the life of a bum. He never could explain what exactly was running through his head when he decided to live the life of a homeless one, but he had interesting stories about the lifestyle. He indicated that there were some things he wouldn't discuss which was just as well. I was probably better off not knowing and let him take some of those tales to his grave.
The old time hobo is often romanticized in pop culture, but I imagine it's a life few of us would live. Without the conveniences of modern dwellings we'd go insane just attempting to light a fire on a daily basis or living off the greens of the land.
So in honor of my grandfather's lifestyle choice I bring you a song that detailed the dreams of many a hobo:
"I have sung in hobo jungles, and I have sung for the Rockefellers, and I am proud that I have never refused to sing for anybody." - Pete Seeger