When you sit back and think about iconic stars of western movies, there's a couple of names who are guaranteed to come to mind — John Wayne and Clint Eastwood. Both stars were major box office draws for the western genre and many of their films are still considered classics. The Duke is known for John Ford's Stagecoach, The Searchers, and The Man Who Shot Liberty Valance, and Eastwood, after getting his start in the TV show Rawhide, became a movie star after appearing in Sergio Leone's spaghetti western Dollars Trilogy. But somehow, the actors never shared the screen together. There's actually a very specific reason why that never came to be.
Part of the problem (at least for John Wayne) was the two men represented different eras of the western film genre. Wayne had been one of the first major western stars in the 40s and 50s and really wasn't a fan of the new way Eastwood's films represented the Old West. He found his films to be a bit too dark and gritty compared to the heroic tales of cowboys he had built his career on. Just a couple of years after Wayne had earned his only Oscar for True Grit, he was approached by a director named Larry Cohen who wanted him to star in a western opposite Eastwood.
The film was called The Hostiles and would follow a young gambler who won land off an older man. Eastwood was interested in the film, set to play the gambler opposite the elder Wayne. But The Duke refused. He hated the script, hated the way it was depicting the Old West, and more importantly, just straight up didn't like Clint Eastwood as an actor. Eastwood apparently reached out to Wayne trying to get him interested in the film but the Dirty Harry star was in for a real surprise.
Wayne decided to write Eastwood a letter not only saying no to the script but criticizing Eastwood's recent film High Plains Drifter. Wayne couldn't have been less impressed with the film. It's interesting to think about what he would say now considering Eastwood has gone on to direct multiple Oscar-winning films, including the western Unforgiven. But at the time...he was not a fan.
According to the book Ride, Boldly Ride: The Evolution of the American Western, Eastwood explained, "John Wayne once wrote me a letter saying he didn't like High Plains Drifter. He said it wasn't really about the people who pioneered the West. I realized that there's two different generations, and he wouldn't understand what I was doing. High Plains Drifter was meant to be a fable: it wasn't meant to show the hours of pioneering drudgery. It wasn't supposed to be anything about settling the West."
The actor apparently never wrote back and that was that. The Hostiles was never made and the two actors never worked together. High Plains Drifter didn't end up becoming a major hit with audiences either, but it did help introduce Eastwood to the world as a director (following his directorial debut, Play Misty For Me) and changed the trajectory of his career. Either way, it's a shame the world never got to see these two legends work together — a missed opportunity to bring together two generations of western icons.