Frank Sinatra Was Offered This
He thought about taking it, since pal Dean Martin was playing Matt Helm in another series of spy spoofs.
Doubt that old Frank would have been up to some of the Coburn stunt work, though.
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Later on they also wanted Frank for DIRTY HARRY
Yep. Sinatra was signed and almost MADE "Dirty Harry," but a hand injury forced him out.
Sinatra was a great star in his fifties/early sixties peak, but he wouldn't have been a very good Dirty Harry in 1971, in his later years as a star.
And no way, a Derek Flint, even in 1966. Too middle-aged.
Fox came to Sinatra with a much more fitting character in 1967: "Tony Rome," a Bogart-like middle-aged private eye working out of Miami Beach whose fighting skills were most believably mundane.
Derek Flint? No.
Harry Callahan? No.
Tony Rome? Ring-a-ding-ding, baby.