- Anachronisms: People in the saloon sing "A Bird in a Gilded Cage." The scene takes place in 1892; the song was written in 1900.
- Continuity: Towards the end of the film, Robert Ford shoots, then throws the gun on the floor. The gun disappears when Robert Ford leaves.
- Anachronisms: When Robert Ford is working in the general store, a bicycle leans against the wall. It's supposed a Highwheel, Ordinary, or Pennyfarthing bike. However, it's a contemporary model, intended for use by circus and parade riders, and only superficially similar to a period bike.
- Anachronisms: When the gang leaves Martha's farm for Kentucky, Dick Liddil carries a pair of saddle bags. The pattern on the bags the US Army M1885 Pattern, which first appeared 5 years later.
- Anachronisms: When Bob sends a telegram announcing that he has killed Jesse James, he goes into an American Telegraph Company office and uses an American Telegraph blank. American Telegraph merged with Western Union in 1866. The blank correctly identifies E. S. Sanford as American Telegraph's president, but the date (1882) is fake. Furthermore, American Telegraph's lines ran along the Eastern seaboard, from New York to New Orleans. St. Joseph, Missouri, was in the territory of Illinois & Mississippi Telegraph Company, which later merged with Western Union.
- Continuity: In every scene where Jesse smokes a cigar, the length of the cigar as well as the size of the ash at the foot of the cigar varies tremendously across shots. Such variation cannot be accounted for by normal burning off of the cigar as one smokes it.
- Revealing mistakes: Toward the end of the movie, a closeup shot of Casey Affleck's face reveals a noticeable hole from an earring piercing.
- Continuity: When Wood Hite is shot, he falls to the floor with one leg straight, the other bent at the knee, one arm flat on the floor, the other hand resting on his stomach. When Bob Ford rises to see if Hite is dead, both Hite's legs are straight, flat on the floor, as are both arms.
- Errors made by characters (possibly deliberate errors by the filmmakers): When the photographer photographs Jessie James's corpse, he replaces the lens cap on the camera and then thanks everyone for standing still. He then removes the film holder from the back of the camera and doesn't insert a dark slide to protect the sheet of film. Either the film would have gotten ruined, or if the dark-slide wasn't removed before taking the photo, no image would have been recorded.
- Continuity: In the scene where Jesse is shot By Robert Ford, his wife is laying over him screaming and crying. The whole while Jesse's eyes are closed, at one point they cut to Robert, and cut back, Jesse's eyes are clearly wide open. They cut back and away once more and his eyes are closed again.
- Factual errors: When speaking about the last robbery, Wells Bank, Jesse states to Bob that Platte City is 30 south of Kansas City. It's actually 30 miles NORTH of Kansas City.
- Plot holes: At the end of the film, we see Robert Ford in his saloon / dance hall, Ford's Exchange, which is an actual building. When he is shot soon after by Edward O'Kelley, again in his own establishment, it is suddenly a tent saloon. Perhaps due to editing, it is not explained that this is a temporary location Ford operated out of while waiting to rebuild the dance hall seen earlier - it had been destroyed in a fire that ravaged Creede, Colorado's downtown area three days before Ford was killed.
- Continuity: After chopping off the heads of two snakes wrapped around Brad Pitt's arm, they are alive again in the next shot, the shot obviously placed out of order.
- Anachronisms: As the gang members wait during the day, to rob the train at Blue Cut during the night, one gang member recites a poem of Catullus ("My love says she would marry only me ..."); the words he recites are from a translation published in 1970, "Catullus: The Complete Poems for American Readers", by Reney Myers and Robert J. Ormsby.
>>> WARNING: Here Be Spoilers <<<
Goofs below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- Revealing mistakes: SPOILER: When Bob shoots Wood, the bullet rips through Wood's head. As Wood falls, there is no bullet hole on the wall, or a single drop of blood.
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