Clint Eastwood rejected the script for wannabe - only for John Wayne to snap it up. Many screen icons were considered for the titular role in Dirty Harry, including Paul Newman, Frank Sinatra and John Wayne. They all rejected it for one reason or another, be it the violence involved or perceived political incorrectness. Of course, it was the film that cemented eventual lead Clint Eastwood as an A-list star, and Harry remains one of his most famous characters; Eastwood later reprised the role for another four Dirty Harry movies.

The film's rogue main character and pushing of boundaries led to other projects trying to recapture the same lightning. One key example would be 1974's Death Wish starring Charles Bronson, which was arguably even more controversial. Two more instances include McQ and Brannigan, both of which starred John Wayne. Both thrillers cast Wayne as tough detectives who carry Magnum revolvers and bend the rules to see justice done. In short,

While being interviewed by journalist Paul Nelson (via Conversations with Clint: Paul Nelson's Lost Interviews with Clint Eastwood, 1979-1983), Eastwood was asked several questions about Wayne and his thoughts on the screen icon's final film, The Shootist. This led Nelson to label Wayne's "imitation Dirty Harry" as plain "embarrassing." Presumably passing judgment on both McQ and Brannigan, Eastwood replied:

I know. In fact, one of them was originally written for me: McQ. I passed on it.

Much has been made of a supposed feud between Eastwood and Wayne, though the latter once told Clint, "We ought to do a movie, kid," as his career was taking off. By this point, Clint had become the face of a darker, more violent and cynical breed of Western, right as the genre's popularity was waning. . This signals how Wayne felt he missed the boat the first time out.

Of course, it was wise for Eastwood to turn down another rogue cop movie like McQ, since he had already signed on for Dirty Harry sequel Magnum Force. Still, , and if nothing else, confirmed that "The Duke" was wrong for the role anyway. The movies themselves are cliché detective thrillers that lack Dirty Harry's edge, though they at least stage some effective setpieces.

Dirty Harry is a screenplay that traveled around before it landed on Eastwood's desk. The title character was intended to be older than Clint was at the time, which is why Hollywood vets like Paul Newman or Frank Sinatra got first dibs. In fact, , as he needed an operation on his wrist. Wayne wasn't too pleased that he was approached about the role after Sinatra exited, either.

According to John Wayne: The Man Behind the Myth, Wayne said, “I didn’t like being offered Sinatra’s rejections." During this period, Wayne was largely sticking to Westerns, having recently won an Academy Award for True Grit. Many of his follow-ups, like Rio Lobo (the final film of movie legend Howard Hawks) and Cahill, U.S. Marshal, played like tired retreads of movies he had made many times before. Something like .

Even so, it would have been a different film with Wayne as Harry. His distaste for bloody screen violence or vulgarity would have seen those elements toned down, for example. Still, Wayne publicly stated his regret at passing on , feeling it was an updating of the kind of Western characters he had played before. That's what attracted him to projects like and Brannigan, but accepting lesser versions only proved to be another mistake.

Source: Conversations with Clint: Paul Nelson's Lost Interviews with Clint Eastwood, 1979-1983, John Wayne: The Man Behind the Myth