As for why Sinatra left Dirty Harry, Davi shared: “Milius brought the .357 Magnum with him to show Sinatra. They were telling him the story and they go, ‘And this is going to be your gun’. And Sinatra picked up the gun and said, ‘I’m afraid it’s a little too big for my hands’ and that’s why he turned it down.”
Another alleged reason is that the singer broke his wrist while filming The Manchurian Candidate, meaning he couldn’t hold the weapon properly. As for John Wayne, Duke turned Dirty Harry down as he “didn’t like being offered Sinatra’s rejections.”
Other Hollywood stars of this era had their own varied reasons for passing on the 1971 classic.Robert Mitchum thought the film to be “a piece of junk”, while both Burt Lancaster and George C Scott couldn’t handle the violence.
Steve McQueen had already made 1968’s Bullitt and refused to do another cop, movie, believing the character to be too right-wing for him. Paul Newman also passed on Dirty Harry but was the one to suggest that it be a good part for Eastwood.
The latter said years later: “So I said, ‘I’ll do it,’ but since they had initially talked to me, there had been all these rewrites. I said, ‘I’m only interested in the original script’. The rewrites had changed everything. They had Marine snipers coming on in the end. And I said, ‘No. This is losing the point of the whole story, of the guy chasing the killer down. It’s becoming an extravaganza that’s losing its character.’ They said, ‘OK, do what you want.’ So, we went and made it.