The closest that Eastwood ever got to working with Wayne was when his frequent collaborator and filmmaking mentor, Don Siegel, directed The Duke in his final screen performance in 1976, The Shootist. Wayne was offered a chance to star with him in The Hostiles, an abandoned project that would hypothetically feature Eastwood playing a young gambler who wins a large portion of an old man's estate. This letter was sent directly in response to Eastwood's proposal to Wayne to star together in a film. After the film's release, Wayne sent Eastwood a scathing letter, stating that "it wasn’t really about the people who pioneered the West," according to Eastwood. evil and the upstanding role of Western protagonists, was disgusted by Eastwood's depiction of the Old West. Wayne, a traditionalist in his view of good vs. Unforgiven, which is considered the pinnacle of revisionist Western mythmaking, was not the first time that the star reconsidered the supposed heroism at the heart of cowboy icons. The outlaw justice that Eastwood's Stranger character delivers to the town in the film is satanic, blurring the line between good and evil. High Plains Drifter, which follows a mysterious gun-fighter (Eastwood) hired by a local town to defend its people against three violent outlaws, is a dark, revisionist examination of the cowboy figure that audiences were trained to cheer for throughout the history of Hollywood. In an alternate universe, the latter of the two films, which was Eastwood's second bid as a director, could have been a proper passing of the torch between the old guard and the new face. With his contributions to Westerns, including the 1968 film Hang 'Em High and the 1973 film High Plains Drifter which he also directed, the actor was destined to take the mantle from Wayne as the new face of the genre. Thanks to the acclaimed original Dirty Harry and its four sequels through the next decade, Eastwood was molded into a cultural icon representing masculinity, noble anti-heroism, and the arbiter of justice - mirroring the iconography of Wayne. On the flip side, Eastwood was steadily climbing up the ladder to stardom, starting on TV with Rawhide, morphing into an international star with Sergio Leone's "Dollars" Trilogy, all of which accumulate to the role that would cement his legendary status, Harry Callahan. At the 1970 Academy Awards, Wayne was honored with his first-ever Oscar for True Grit- a career achievement of sorts that the awards body is prone to give out. When Eastwood emerged as a major movie star in the early 1970s, Wayne's glory days were behind him.
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