Clint Eastwood’s signature ‘Dirty Harry’ role was originally planned for someone else

“You’ve got to ask yourself one question: Do I feel lucky?”

For Clint Eastwood, luck came his way when he landed the part of “Dirty” Harry Callahan in Don Siegel’s gritty cop drama from 1971, but it wouldn’t have happened if someone else hadn’t first left the project.

Eastwood was certainly a known quantity by the beginning of the 1970s. He’d starred on eight seasons of Rawhide and led Sergio Leone’s “Man With No Name” trilogy — the legendary “spaghetti Westerns” A Fistful of Dollars, For a Few Dollars More, and The Good, the Bad, and the Ugly. He also had his directorial debut, Play Misty for Me, already in the can. Still, getting cast as the quintessential ends-justifies-the-means tough guy police detective with the Magnum .44 is what turned him from a star into a superstar with the clout to call his own shots in Hollywood.

So who was it the studio originally had in mind for the role? Could you imagine trading Dirty Harry’s squinty eyes for… Ol’ Blue Eyes?

Yes, it’s true. Frank Sinatra was all set for the part, and was actively involved in the development of the movie. In this unearthed radio interview from 1970, he speaks with a San Francisco DJ about coming to town to shoot the movie there. In fact, he says that it was his idea to move the location from New York City to San Francisco — which is fascinating when you consider that Dirty Harry is loosely based on the actual Bay Area menace “The Zodiac Killer,” and that Eastwood is so closely associated with the region. In the clip, Sinatra says that the city has “never been photographed as well as it should be.” (You’ll also hear that he and Warner Bros. were trying to secure a director like John Frankenheimer, who had directed Sinatra in 1962’s The Manchurian Candidate.)

While most people think of Sinatra as a crooner associated with the Great American Songbook, it’s important to remember that he was a box office draw for decades, and had several non-musical or “Rat Pack”/Ocean’s 11/Robin and the 7 Hoods-type roles.

Sign up for Entertainment Weekly‘s free daily newsletter to get breaking TV news, exclusive first looks, recaps, reviews, interviews with your favorite stars, and more.

Indeed, prior to what would have been his turn in Callahan (as Dirty Harry was called at the time), Sinatra appeared in the cop drama The Detective and he made two gritty private eye pictures, Tony Rome and its sequel Lady in Cement. Earlier in his career, he played an assassin in Suddenly and he was also in the war adventure Von Ryan’s Express. The point is, it wouldn’t have been so nuts to cast him in something like Dirty Harry.

But it is nuts to try and imagine anyone other than Clint Eastwood in the film or its four (four!) sequels, spitting out classic lines like “Go ahead, make my day” or using “enhanced interrogation techniques” against Andrew Robinson’s deranged killer, Scorpio.

So why did Sinatra leave the project? Well, the specifics are a little hazy, but for a while, he was going to shoot it with director Irvin Kershner, who would later make The Empire Strikes Back, and also William Friedkin, who went on to helm The French Connection. Sinatra had recently undergone hand surgery and, supposedly, he had trouble holding Det. Callahan’s enormous gun. That’s the official reason he walked away.

Different tellings of the tale make it unclear who was still planning to direct when Sinatra stepped down, but the point is that Sinatra, Kershner, and Friedkin all left the project, and several other known stars like John Wayne, Robert Mitchum, Steve McQueen, George C. Scott, and Burt Lancaster all passed on the part. (Honestly, Lancaster would have been a brilliant pick.) So it landed with Eastwood and Don Siegel, who had already directed Eastwood in Coogan’s Bluff, Two Mules for Sister Sara, and The Beguiled. And the mid-budget film became a cultural sensation.

The sequels Magnum Force, The Enforcer, Sudden Impact (the one with the “Make my day” quote), and The Dead Pool followed, as did the term “Dirty Harry” as a euphemism for a cop who gets results by any means necessary.

The movies were provocative by design, and many critics condemned the movie. Pauline Kael notably led the charge, writing that action-heavy cop movies “always had a fascist potential, and it has finally surfaced.” Eastwood’s response was less than kind, but he balanced out his karma by directing movies like the Charlie Parker biopic Bird, the lovelornThe Bridges of Madison County, and the competence porn exercise Sully — as well as the dramas Unforgiven and Million Dollar Baby, two Best Picture Oscar winners.