The film Dirty Harry turned 37 in June of this year. A just released collector’s edition has been stirring up a lot of comment and intrest in the film again.
Eastwood has been interviewed again and again about his iconic portrayal of the rogue cop, but a recent MTV interview included the following exchange.
MTV: You were not the only big name attached to Dirty Harry. Frank Sinatra very nearly played the part.
Eastwood: I guess they tried to get a lot of people for it. They tried Frank Sinatra and Robert Mitchum and Steve McQueen. Then they finally ended up with Frank Sinatra. I was in postproduction (on Play Misty for Me), and 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." But since they had initially talked to me, there had been all these rewrites. I said, "I'm only interested in the original script."
It’s enough to make you wonder exactly what ‘Ol Blue Eyes would have done with the role. And as far as Sinatra not being able to hold a gun, he certainly did so in such films as The Detective and Tony Rome – however, in those films he carried a snub-nosed .38. It could be he couldn’t handle the massive Magnum .357 as required for the character. On the other hand, I think it would have been kind of cool to see Sinatra, through clenched teeth, delivering the line, “Go ahead, punk. Make my day!”
For me Sinatra’s best turn as a cop character was in 1980’s The First Deadly Sin based on a terrific novel by Lawrence Saunders.The image at the top of this post is from a trade ad which appeared in the Nov. 9, 1970 issue of Boxoffice magazine, promoting the then In Production Warner Bros. release Dirty Harry, and offers a rare glimpse of Sinatra's Harry Callahan.