Riding the Rails(1988)

“Fallen Wall Street yuppie turned hobo train-hopping across America in search of work and a new life.”

Overview

Wiped out by a stock market crash, Sam Spencer suddenly finds himself broke and homeless in New York. When a friend offers him a job in California, Sam heads west the only way he can afford, hopping trains. Along the way, he befriends Enrique, an illegal immigrant from Mexico, and Enrique's canine companion who together introduce Sam to hobo culture.