7. Frank Sinatra As Harry Callahan - Dirty Harry
It's hard to imagine that anybody other than Clint Eastwood could have played Dirty Harry, and yet there was a time when - would you believe? - Frank Sinatra almost ended up embodying the famous role. Yes, before Clint Eastwood was even attached to the project, Ol' Blue Eyes was cast as the titular Detective Harry Callahan, and was even featured in various marketing campaigns and posters which poised him as the cool lead in an upcoming film "directed by Irvin Kershner." But Sinatra never got the film (nor did Kershner), thanks to an untimely injury. Yes, whilst on the set of The Manchurian Candidate, Sinatra broke his wrist, which meant that he was unable to wield Dirty Harry's famously huge gun. As a result, he was forced to pass the role on to somebody else. Firstly, John Wayne was considered, but he rejected the opportunity on the basis of not wanting one of "Sinatras rejections. Eventually Eastwood read the script and agreed to play Harry.