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  • Complete Monster:
    • Original film: Captain Terrill is the bloodthirsty leader of the Redlegs, a group of pro-Union looters and pillagers who open the film torching the titular character's house to the ground and murdering his family, including his young son. Enlisted as a genuine federal authority by Senator Lane in order to dispose of any holdouts at the end of the Civil War, Terrill exercises his new power by having his Redlegs massacre a group of surrendering Confederates who had been promised amnesty and mortally wounding one of the escaping survivors himself. Terrill begins a ruthless manhunt for Josey Wales across the countryside after he escapes the carnage, with full intent to move onto Texas afterwards and continue killing rebels, coldly remarking that "Doin' right ain't got no end."
    • The Return of Josey Wales: Captain Jesus Escabedo is the sadistic chief of police in a Mexican town still loyal to the deceased Emperor Maximilian. Escabedo makes a recurrent hobby of riding out to scalp native Apache people, with a proclivity for collecting the skulls of the infants. Escabedo has a woman gang-raped to death, dismissing her as "another whore with dreams", and personally beats the one witness to it half to death before shooting him dead. Escabedo later has an Apache woman brought to his quarters for his own personal entertainment, beating her bloody when she resists him and promising her she'll hang for the rest of her people to see her.
  • Memetic Mutation: Josey's comment to a Bounty Hunter he urges to walk away from a fight. "Dyin' ain't much of a living', boy."
  • One-Scene Wonder:
    • Will Sampson as Ten Bears, displaying honor and dignity as he makes peace with Josey Wales, and gets one of the more memorable monologues in Western film history.
    • The Anti-Villain Bounty Hunter Josey faces in Santo Rio, due to how (in contrast to the other bounty hunters who face Josey) he seems to dislike his profession, doesn't mock Josey, and faces Josey in a fair fight despite realizing he may be outclassed by the hardened fugitive. He's also on the receiving end of perhaps the biggest Memetic Mutation of the film.
  • They Wasted a Perfectly Good Character: Jamie dies at the end of the first act, but his strong performance and established relationship with Josey causes many fans to wish that he'd survived to meet the rest of the supporting supporting cast and join them in their Family of Choice.
  • Values Dissonance: While this movie has aged a lot better than many other Civil War films of the era in terms of mores, there are still things that might rankle certain audience members in the 21st century.
    • During the 1960s and 1970s, many critics of the federal government identified with the Confederacy, no matter what their political persuasion. One standout example is how a far-left group allied with the Black Panthers known as the Young Patriots Organization used the Confederate battle flag as their symbol. Nowadays, however, the movie's implications that the Union didn't hold the high ground in the conflict would raise quite a few hackles.
    • The use of the Noble Confederate Soldier trope would likely be met with far more controversy today, considering the discrediting of Lost Cause historiography and increased knowledge that the Confederacy existed mainly (if not entirely) out of a desire to continue owning black people as property.
    • Lone Watie is a Noble Savage and while Fair for Its Day, does not sit well with some audiences today.

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