The unusual advertisement you see at right was published in the November 9th, 1970 issue of Box Office magazine. Frank Sinatra as Dirty Harry? Of course, the iconic role of Harry Callahan went to Clint Eastwood – not Sinatra – so what explains this oddity?
At press time, Sinatra was supposed to play the part, but hand surgery, intervened, as it prevented him from holding a gun – no gun, no Dirty Harry. Someone else would have to play the role.
Clint Eastwood – already an established star, thanks to his roles in many classic Westerns of the 60s -got the nod after several different actors were considered, including Paul Newman.
The film was an enormous success, and Dirty Harry was an important turning point in Eastwood’s career, for it helped to further establish him outside the Western genre.
Still, one can’t help but wonder how very different the role might have been had it been played by Sinatra. Perhaps some clues might be found by watching The Detective or The First Deadly Sin.










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