Eddie Dodson was a Hollywood playboy who robbed 64 banks between July, 1983 and February, 1984 - including six on one day. He served almost 10 years in prison, got out and after a few months was offered a job as a housesitter by Jack Nicholson. Jack sent Eddie to drug treatment twice but on Eddie's third relapse, he lost his position. Two weeks thereafter Eddie got off parole. Two weeks after that he started robbing banks again. He robbed eight more (Eddie said nine, the FBI says eight) before getting arrested again. This time he got a sentence of 46 months, owing in part to a failing liver. He served 40 months, got out in October of 2002, and died in February of 2003 of liver failure.
Ewan McGregor was originally cast as Eddie Dodson and Carey Mulligan as his girlfriend but after years in development, both dropped out and were replaced by Jim Sturgess and Isabel Lucas.