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It is 1938, and the United States is still in the worst economic slump of its history - the Great Depression. You leave home and became a hobo when there isn't enough food to feed you and your whole family. You start riding the rails but are having a difficult time adjusting to this wandering lifestyle. It just isn't for you, but right now, you have no choice.
Luckily, you hear about a new reality show called Extreme Makeover:Hobo Edition, which promises to give one deserving hobo a chance for a complete makeover, a new job, and a trip home. You write the producers telling them why you should be chosen for the extreme makeover and, lo and behold, the producers are impressed with your story and choose you from the thousands of hoboes that sent in their sad letters.
Now all you have to do is travel to the show's location to receive the grand prize. You are very excited, but you don't know if you will succeed in getting there on your own. You hook up with an experienced hobo by the name of Boxcar Bob. Boxcar Bob says he will help, but on one condition. You see, Bob used to be a teacher but lost his job when his school closed down because there wasn't enough money to keep the doors open. Boxcar misses his job so much that his condition is this - he will show you the ropes of riding the rails and get you where you need to go. In return, you must study with him to learn all you can about the homeless teenagers who have been riding the rails during the past five years. All it will take is a little reading and a couple of quizzes. "No problem," you respond. "Let's get going!"