The storyline is loosely based on real life bank robbers Terry Lee Conner and Joseph Dougherty. Many elements of their heists are accurately depicted in this film, including breaking into the house of a bank manager, and giving a soda to one of their victims.
Billy Bob Thornton has a phobia of antique furniture in real life, and the producers wrote it in as part of his character.
The little girl who belches during the dinner scene is Bruce Willis' daughter, Scout Willis, and according to him, that belch was not enhanced. The other girl is another one of Willis' daughters, Tallulah Willis.
Many of the people playing inmates in the film were either penitentiary inmates, or correctional officers. The officers dressed as inmates were positioned closer to the wall, to help maintain security.
When Terry wakes up saying "Beavers and Ducks", it's a reference to two arch-rival Oregon college football teams, the Oregon State University Beavers and the University of Oregon Ducks.
Barry Levinson: The last staff to the right of the camera in the studio room from Darren's point of view when he presented "Criminals at Large" at the beginning of the film.