Few people are aware that Frank Sinatra had been offered the part of Harry Callahan in Dirty Harry. But, as this interview with Clint Eastwood reveals, that was precisely what happened. Eastwood’s role as Dirty Harry was, ultimately, a large part of what made him a film icon. It seems hard to imagine now what the series would have been like with Sinatra in the starring role. Different? Absolutely. Better? Maybe not; we’ll never know. But there are other roles one wishes Sinatra had received or completed: Sinatra made a great Nathan Detroit in Guys and Dolls, but I’d be willing to bet most fans would rather have seen him as Sky Masterson instead. Sinatra’s abortive involvement in Carousel - he walked off the picture after learning he would have to film scenes for two different motion picture formats - survives, albeit only in musical form, with tracks recorded for the film appearing on Sinatra in Hollywood 1940-1964.