The script floated around Hollywood for nearly 20 years, during which time Gene Hackman read and rejected it, only to be later convinced by Clint Eastwood (who had owned the rights to the script for some time) to play a role.
Clint Eastwood's mother Ruth Wood toiled through an uncomfortable day (wearing a heavy dress) as an extra, filming a scene where she boards a train; but the scene was eventually cut, with her son apologizing that the film was "too long and something had to go." All was forgiven when he brought her to the Academy Awards and thanked her prominently in his acceptance speech.
The film was shot in 39 days, coming in 4 days ahead of schedule. The town had to be built very quickly, with a relatively short run-up time (2 months) to the start of filming; the construction period was used by the stunt coordinator to work on actors' riding skills and stunt choreography.
This film put paid to Clint Eastwood's longstanding statement why he would never win an Oscar. Eastwood reckoned he would never be in the running because "first, I'm not Jewish. Secondly I make too much money. Thirdly, and most importantly, because I don't give a fuck". Since his double Oscar win for Unforgiven (1992), Eastwood has gone on to win 2 more Oscars as well as an Irving G. Thalberg Memorial Award and has been nominated an additional 6 times.
The boots that Clint Eastwood wore in this film are the same boots that he wore in the TV series Rawhide (1959). These boots are now a part of Eastwood's private collection and were on loan to the 2005 Sergio Leone exhibit at the Gene Autry Museum of Western Heritage in Los Angeles, California. In essence these boots have book-ended Eastwood's career in the western genre.
Deputy Clyde's line about why a one armed man needed to carry three pistols: 'I don't want to get killed from lack of being able to shoot back' is sometimes attributed to lawman/gunfighter Wild Bill Hickok who usually carried two pistols around his waist, another in a shoulder holster, sometimes another stuck in the back of his belt, and usually had at least one Derringer hidden somewhere on his person. While working as a lawman, he usually carried a sawed off shotgun as well. Hickok also laughed at Ned Buntline's report about his killing 20 men with 20 shots saying that his theory was start shooting and keep shooting until the man you were shooting at was dead.
Most of the rain in the film was specially created because Calgary, where it was shot, was experiencing a dry spell, though the snowfall that is featured when William Munny is recovering from his beating was unexpected (and unscripted).
According to Clint Eastwood in a 2000 interview, Gene Hackman was very concerned about how they were going to show the violence in the movie, owing to the rising gun violence in American cities. Eastwood assured Hackman that the film wouldn't glorify gun violence.
In the early 1980s, Francis Ford Coppola got hold of the script and met with John Malkovich to offer him the role of Williams Munny. Malkovich recalled: "The offer was not very serious - thank God! I say that for myself and the poor public. And for Clint - absolutely! I would have been a total, total failure. Total! Who would've wanted to see that? I wouldn't! I would've just been acting-schmatching. There are some things you can only have with a kind of mythic figure which Clint is."
The windmill that appears in the backdrop through much of the movie was a real operating windmill, rather than a set piece, and to this day pumps water to The Dow Wetlands Preserve in Antioch, California, where it was sent after shooting.
The following guns were used in this movie. 1. William Munny used a 1859 Starr revolver double action, a Smith and Wesson Schofield revolver, a 12-gauge double barreled coach shotgun, and later a Spencer rifle. 2. Ned uses a Spencer rifle. 3. The Kid uses a S&W Schofield, and earlier he uses a Winchester 1873 rifle. 4. English Bob uses a Colt 1873 "Peacemaker" Single action Army and a Bulldog .32 caliber pocket pistol. 5. Little Bill used a Colt 1873 "Peacemaker" Single action Army. 6. The Cathouse owner has a Colt 1851 single action revolver. 7. Andy the deputy uses a Winchester 1866 "Yellow Boy" made to look like a Henry rifle by removing the for-end. 8. The one armed law man uses 3 revolvers one a Remington 1875 and 2 Colt 1873 "Peacemakers". 9. Various people stick to the famed "peacemakers" and Winchester '73 rifles.
The tavern in which the final scene takes place is called Greeley's. It is a reference to New York Tribune editor Horace Greeley who is often incorrectly attributed with writing the line "Go West Young Man." That line was actually written by John B.L. Soule. The phrase "Go West, Young Man" is often attributed to New York Tribune founder Horace Greeley, and often misattributed to Indiana journalist John B. L. Soule, but the latest research shows it to be a paraphrase.
With this film being an Oscar winning western, Clint Eastwood went on to direct and star in A Perfect World (1993) the following year. Eastwood and co-star Kevin Costner had something in common, as Costner had also directed and starred in an Oscar winning western, which was Dances with Wolves (1990).
By Clint Eastwood's own recollection he was given the script in the "early 80s" although he did not immediately pursue it, because according to him "I thought I should do some other things first." Biographer Patrick McGilligan specifies that it was presented to him in the spring of 1984 by Megan Rose, a story analyst at Warner Bros. whom Eastwood happened to be sleeping with at the time.
Frances Fisher was nearly four months pregnant with Francesca Eastwood when she went to the Academy Awards, but had been under strict orders not to tell anyone, including her closest friends. Clint Eastwood reportedly said to her, "I don't want that kinda thing taking attention away from my Oscar race!"
When Will notes that Ned is still using a Spencer rifle, it would imply that Ned carried it in the Civil War as a member of a U.S. Colored Troops cavalry regiment. Morgan Freeman also starred in Glory (1989) as a member of a U.S. Colored regiment