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All the train hopping footage is real, as far as I can tell. Barry’s got a thing for it. This from Clamor Magazine:

Tim’s first train hopping experience was in 1993 with two friends, Naomi, who was also experiencing it for her first time and Ronny “Richmond” who was actually from Maryland. Ronny had been the experienced rider and had learned all that he knew about riding from his uncle. The ride was from Richmond, Virginia to Rocky Mountain, North Carolina. Ronny had told Tim and Naomi to wait under a bridge while he went and talked to one of the rails. He found out the line that they needed and before he returned had already selected a boxcar for the ride. Tim loved it. After riding with others a few more times, learning the basics, and getting the feel for it, Tim began to ride on his own.

A streamline rider is typically equipped with only a bag filled with the essentials: food, water, and enough cash for about a week on the rails, which as you can imagine probably really wouldn’t be that much cash, considering you’re not paying for a ticket, and won’t be spending much time in the dining car. Tim uses his time on the trains to take himself out of his day-to-day life and allow for new perspectives. “Songs will just start popping up when I’m not in my normal [routine]. Everything starts coming together. I’ll write tons and tons of songs before I leave for trips, when I get home, and when I’m on them. It’s very rhythmic. There’s something about the click on the tracks. I find myself writing rhythms and lyrics.”

“Sometimes I feel at peace. Sometimes I feel real paranoid. It’s such a thought progression when you’re on a train. Sometimes I’m like, why the fuck am I on this? Or, this is the best thing in the world. Or, I just want to be home. I just watch. Watch the cotton fields pass. I think it was Duffy Littlejohn [author of Hopping Freight Trains in America] that said, ‘It’s the last red-blooded American frontier,’ and I back him on that.”