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Clint Eastwood as the title character in the 1971 film ‘Dirty Harry’ (AP Photo/Warner Bros.) Dirty Harry’s vigilante police detective Harry Callahan is one of the defining roles of Clint Eastwood’s career — but it was meant to be played by Frank Sinatra. In an interview for Alec Baldwin’s podcast Here’s the Thing, director William Friedkin (The French Connection, The Exorcist) revealed that he’d spent months developing the gritty 1971 crime drama with the crooner-turned-actor in mind. “My producer, a guy named Phil D’Antoni, he and I were going to do Dirty Harry with Frank Sinatra,” said Friedkin.
Clint Eastwood as the title character in the 1971 film ‘Dirty Harry’ (AP Photo/Warner Bros.) Dirty Harry’s vigilante police detective Harry Callahan is one
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