Here's a good NPR story on hopping freight trains today. The era of the hobo has been replaced by "Catching out"
http://www.npr.org/templates/story/story.php?storyId=18939012 I knew a fellow back in Chicago who used to do this. He'd even written a guide to the best places to grab freights
The pic is taken on SP's famed Tehachapi Loop. That is the SAME train the rider is on up at the top.