A scene with Billy Bob Thornton and Bill Paxton was lost by Northwest Airlines in January 1998 while in transit from Minnesota to Los Angeles. The missing scene had been shot in Minnesota. The film was insured, and the missing scene was re-shot.
Sam Raimi learned some techniques about shooting in the heavy snow from the Coen brothers, friends of his who had been responsible for Fargo (1996).
Between 1994 and 1996, Ben Stiller was set to direct this film with Nicolas Cage to star. When Cage's salary began to affect the film's overall budget, Stiller walked away. The reins were then given over to John Dahl who later left the project to be replaced by director John Boorman. Meanwhile, Emma Thompson was considering the part of Sarah Mitchell but, after a while, declined. Finally, Thomas signed on and Raimi replaced Boorman and production was set to go... three years after the rights were sold to Mike Nichols for a reported $250,000 (U.S.) "against" $750,000.
Bill Paxton's father plays the old man who confronts Paxton's character in the feed store ("Are you mean to tell me that there were five weeks last month?")
Many of the props used in the film where local items: for example the feed store calendar (used in the scene "Are you mean to tell me that there were five weeks last month?") is the State Bank of Delano anniversary calendar (current at the time of filming) which featured photos of historic buildings (some torn down) in the town (and town's past), hence its rustic addition of the prop to the feed store.
A member of ZZ Top (Frank Beard) was flown in for a cameo appearance during the funeral scene. He is barely visible in the film (look for the guy behind the funeral director/ behind white carnation).
The bar scenes were shot in Delano Minnesota. The bar used in the scenes was an old bar that was changed into a private residence in combination with the apartment above. The only real bar in town did not meet filming needs so the crew used the private residence and fixed up the interior to meet the look they were going for.
Brad Pitt and 'Juliette Lewis' were attached to star, but left the film because of scheduling conflicts.
This was the last film to be produced by the now defunct, short lived independent production company, Savoy Pictures. Originally in 1996, Savoy Pictures filed for Chapter 11 bankruptcy, however "A Simple Plan" which was originally to be produced solely by Savoy was forced to negotiate co-production deals with other motion picture studios, one being Paramount which picked up the film for a co-production and distribution.
The clock on the wall in Carl's office, shown while he and Hank are waiting for Neil about 1:45 into the movie, has a name on it of the film's Art Dept Property Master (Amie McCarthy-Winn).