Frank Sinatra was originally offered the role of “Dirty” Harry Callahan but turned it down due to a broken wrist and the size of the gun. Many other actors, including John Wayne and Robert Mitchum, also rejected the role for various reasons. Clint Eastwood ultimately took on the role and the film became a success, sparking a franchise, while Sinatra pursued other projects in his acting career.
The script for Dirty Harry, with its original title of Dead Right, had been put together by writer Dean Riesner, Harry Julian Fink, and R.M. Fink. The script took its inspiration from the true-life Zodiac killings that plagued California in the late 1960s, and its protagonist is based on Dave Toschi, the lead investigator on that case.
Friedkin and D’Antoni prepared for the filming of Dirty Harry for six full months, under the impression that Sinatra would take the role. Until Sinatra didn’t take the role. The real reason, according to film critic Ty Burr’s book Gods Like Us: On Movie Stardom and Modern Fame, was “a broken wrist sustained during The Manchurian Candidate eight years earlier meant that Old Blue Eyes couldn’t hold the heavy Magnum pistol comfortably.”
So the role was then offered to Clint Eastwood, who offered his own opinion on Sinatra passing on the role: “They called up and asked, ‘Are you still interested in Dirty Harry?’ I said, ‘What happened to Frank Sinatra? And they said, ‘Frank Sinatra’s got some problem with his hand and he can’t hold a gun’. That sounded like a pretty lame excuse, but it didn’t matter to me. I said, ‘I’ll do it’.”
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