The Outlaw Josey WaleswasClint Eastwood’s fifth directed film, the second in the Western genre. LikeHigh Plains Drifter, it was a critical smash and remains respected to this day. ButJosey Waleshas a grimmer story behind its production thanDrifter, and it’s not so surprising when viewing it in modern times. However, with the sexual assault scene in the first act ofDrifter, it’s not as ifthat Western classicis an easy watch in the 2020s, either.

But, when it comes toJosey Wales, there’s a direct correlation between what’s troubling onscreen and what is worrisome off it. Specifically, it’s uncomfortable to view Confederate soldiers as heroic and the men of the Union as bloodthirsty and backstabbing. Yet, it’s not surprising that’s how it’s framed when one comes to realizeits source material was written by someone with a long-running affiliation with the KKK.

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The Outlaw Josey Wales Is a Civil War Story

The Outlaw Josey Wales

Clearly inspired by some ofEastwood’s favorite Western movies, even if it stands on its own more often than not,The Outlaw Josey Walesis a revenge tale at its heart. The title character is a Missouri farmer who witnesses his wife and son’s murder at the hands of a group of Redlegs, a guerrilla militant group on the side of the Union. Internally desolate, Wales joins the war alongside some pro-Confederate bushwhackers until General Robert E. Lee surrenders, much to the bushwhackers' dismay.

But Wales is less despondent and more disconnected, just as he was before he was able to distract himself from all the conflict. But he doesn’t have to wait long for more bloodshed, as once Wales' superior officer, Captain Fletcher, arranges for them to turn their weapons in and pledge allegiance to the Union, the Northern soldiers slaughter all the Southerners – except for Captain Fletcher and a young man named Jamie.

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Wales does what he can to exact vengeance on the site of the slaughter, but he and Jamie are then forced to go on the run. And, in their rearview mirror, are the Union soldiers, led by Captain Terrill,the very man who murdered Wales' family. After Jamie succumbs to his wounds, Wales finds himselfalong Native Americanallies such as the elderly Lone Watie and Comanche tribal leader Ten Bears, as well as a Kansas-based woman and her granddaughter, Laura Lee.

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What Makes The Outlaw Josey Wales Important?

For one, it wasthe first of six collaborations between Eastwood and his longtime lover Sondra Lockeas Laura Lee (though, like the subject matter ofJosey Wales, their relationship was troubling). It was also Eastwood’s last Western as director for nine years until the release of thecharmingly supernaturalPale Rider. The same goes for him as an actor, save for the comedicBronco Billyand the musicalHonkytonk Man.

The film was also another terrific role for Will Sampson, who portrays Ten Bears after playing the iconic Chief Bromden in the previous year’sOne Flew Over the Cuckoo’s Nest. Sampson would go on to have roles in the Charles Bronson-ledThe White Buffalo, theJawsrip-offOrca, and 1986’sPoltergeist II: The Other Side.

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Furthermore, the film was originally to be directed by Philip Kaufman, who wanted to tone down the anti-government stance of the novel,even going so far as to call its author, Asa Earl Carter, a “crude fascist.“But Eastwood wanted to adhere to the book as much as possible and fired Kaufman. Yet, even still, much of the script’s construction was overseen not only by Kaufman (who directed the sublimeThe Invasion of the Body Snatchersin 1978 andThe Right Stuffin 1983) but also by Michael Cimino. Cimino had previously directed Eastwood in 1974’sThunderbolt and Lightfoot(a film Cimino also wrote), but he’s far more well known for the smashingsuccess of 1978’sThe Deer Hunteras well as the nearly career-halting failure of his subsequent movieHeaven’s Gate.

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Who Was Asa Earl Carter, and How Is He Connected to the KKK?

Besides being just a generally problematic individualwith racist viewpoints,Asa Earl Carter was a speechwriter. Specifically for the staunchly pro-segregation Alabama Governor George Wallace. Carter even wrote what would become Wallace’s most historically important utterance: “Segregation now, segregation tomorrow, segregation forever.”

Other problematic aspects of Carter’s personality included running for Wallace’s position on a white supremacist ticket and, before his writing career,hosting a segregationist radio show. He also formed the notoriously volatile Ku Klux Klan faction,The Original Ku Klux Klan of the Confederacy.

And on top of being a stark, loudmouth bigot utterly unafraid to make his hateful views known, Carter was also a hypocrite. Why? Because, despite his racism and antisemitism (the latter of which was too much even for the white supremacist White Citizens' Council), Carter passed himself off as a Cherokee man named Forrest Carter so he could sell his so-called autobiographical memoir,The Education of Little Tree(viaThe Guardian). So, if Carter can be sincerely credited with anything positive, it’s that he made James Frey and hisA Million Little Pieceslook slightly less morally bankrupt and emotionally manipulative.The Outlaw Josey Walesis available to rent onPrime Video.