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), which Billy Bob Thornton appears in the TV spin-off of.
During a 2002 interview on the National Public Radio program "Fresh Air," Bil Paxton told interviewer Terry Gross that he didn't know that his own father had been cast in this movie (in the small role of Mr. Schmitt) until he arrived at a production office at the start of filming and saw his father's headshot on the wall among the other cast members'. It turned out that John Paxton had written a letter to director Sam Raimi saying, "I've always admired your films, and I was wondering if there were any small parts that I'd possibly be right for." And Raimi gave him an audition.
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.
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, 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.
Many of the props used in the film were 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.
Originally intended to be produced by Savoy Pictures. "A Simple Plan" was in pre-production when Savoy went out of business and began to sell its upcoming projects to other motion picture studios, one being Paramount which picked up the film for production and distribution.