The Newton Boys (1998)

Over the course of five years (1919-1924) the Newton Boys, a group of brothers, were the most successful bank and train robbers in North America, traveling from Texas to Toronto without ever firing a fatal gunshot. Willis Newton is the eldest brother who is determined to improve the fortunes of the family by becoming a "businessman" whose business is bank robbing. With the rationale that all banks are insured--insurance companies being the biggest crooks--the brothers begin their spree. By 1924, they execute the biggest train robbery in American history, stealing $3 million outside of Chicago. All goes smoothly until Joe accidentally shoots his brother Doc. Going against the odds, they decide to take Doc to a doctor. The court trial that follows sees the boys and their partners sentenced to prison.