Clint Eastwood gave his son a key role inThe Outlaw Josey Wales, a Western he claims features his best performance.Clint Eastwood’s Westernshelped redefine the genre, with the likes ofHigh Plains DrifterandPale Riderpresenting a darker, more cynical vision of the Old West than Hollywood’s “Golden Age” ever did.

This may have ledJohn Wayne to pass on working with Eastwood, but Clint truly blazed his own path as a Western star. TheDollarstrilogy orUnforgivenmay take most of the attention from movie fans, butit’s not a hot take to call his 1976 WesternThe Outlaw Josey Walesone of Clint’s best films.

Kyle Eastwood as Josey’s son in The Outlaw Josey Wales

This novel adaptation cast Eastwood as the titular, revenge-seeking gunslinger; along the way, however, he regains his humanity when he forges a new family for himself.Eastwood controversially firedThe Outlaw Josey Wales' original director Philip Kaufmanduring production and then took over the film.

This led the DGA to create the “Eastwood Rule,” which prevents an actor or producer firing a director during production and taking the job themselves. This bad business aside,The Outlaw Josey Walesis truly one of Eastwood’s best, and is filled with great characters, dialogue, rousing setpieces and a surprising amount of emotion.

Clint Eastwood on the cover of The Outlaw Josey Wales

The movie opens on a bleak note, showing Josey working with his son on their farm when they are attacked by pro-Union paramilitaries; they murder Josey’s wife and child and leave Wales with a large facial scar. From that moment on, the former farmer becomes consumed with vengeance, with the story covering his journey towards regaining his humanity.

If there’s a reason the opening between Wales and his son feels extra poignant, it’s that the boy is played by Clint’s own child, Kyle Eastwood.Kyle would have been around 7 when he appeared inThe Outlaw Josey Wales, and while he went uncredited for the role, his death haunts the whole movie.

The Outlaw Josey Wales - Poster

Kyle made several cameos in his father’s work, includingClint’s favorite Western of his ownBronco Billy,and 1990’sThe Rookie.Kyle’s biggest role came with the touching 1982 musical dramaHonkytonk Man, where the young Eastwood plays the nephew of Clint’s dying country singer. After retiring from acting, Kyle became a musician and film composer.

Why The Outlaw Josey Wales Is One Of Clint Eastwood’s Most Personal Movies

In the interview bookConversations with Clint: Paul Nelson’s Lost Interviews with Clint Eastwood, 1979-1983,Clint claimsDirty HarryandThe Outlaw Josey Walesare among his best performances. He takes it a step further with the latter, stating “Josey Wales maybe is as good as I can do it.”

Far from being the stoic Man with No Name from theDollarstrilogy, Josey Wales is a far more emotional character. In a rare move for Eastwood onscreen, he’s seen weeping over his son’s grave, andClint has labeled the Western both an anti-film and being about “the rejuvenation of a cynic"who had given up on life.

A sequel calledThe Return of Josey Walesarrived in 1986, with Michael Parks replacing Clint Eastwood as both star and director.

Eastwood’s performance is all the more impressive because he conveys so much of the character with little dialogue. The heart at the core ofThe Outlaw Josey Walesis a key reason it remains so popular almost a half century later, with Clint also claiming it’s the Western he gets asked about the most.

Source: Conversations with Clint: Paul Nelson’s Lost Interviews with Clint Eastwood, 1979-1983, CBS News