Warner Bros. Pictures/Sunset Boulevard/Corbis via Getty "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 ofRawhideand ledSergio Leone's "Man With No Name" trilogy — the legendary "spaghetti Westerns"A Fistful of Dollars,For a Few Dollars More, andThe 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. FilmPublicityArchive/United Archives via Getty 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 Sinatrawas all set for the part, and was actively involved in the development of the movie. In thisunearthed radio interviewfrom 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 thatDirty Harryis 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 likeJohn Frankenheimer, who had directed Sinatra in 1962'sThe Manchurian Candidate.) Michael Ochs Archives/Getty 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 forEntertainment Weekly's free daily newsletterto 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 inCallahan(asDirty Harrywas called at the time), Sinatra appeared in the cop dramaThe Detectiveand he made two gritty private eye pictures,Tony Romeand its sequelLady in Cement.Earlier in his career, he played an assassin inSuddenlyand he was also in the war adventureVon Ryan's Express. The point is, it wouldn't have been so nuts to cast him in something likeDirty Harry. But itisnuts 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" againstAndrew 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 directorIrvin Kershner, who would later makeThe Empire Strikes Back, and alsoWilliam Friedkin, who went on to helmThe 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 likeJohn 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 inCoogan's Bluff,Two Mules for Sister Sara, andThe Beguiled.And the mid-budget film became a cultural sensation. FilmPublicityArchive/United Archives via Getty The sequelsMagnum Force,The Enforcer,Sudden Impact(the one with the "Make my day" quote), andThe Dead Poolfollowed, 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,writingthat action-heavy cop movies "always had a fascist potential, and it has finally surfaced." Eastwood's response wasless than kind, but he balanced out his karma by directing movies like the Charlie Parker biopicBird, the lovelornThe Bridges of Madison County, and the competence porn exerciseSully —as well as the dramasUnforgivenandMillion Dollar Baby, two Best Picture Oscar winners. Read the original article onEntertainment Weekly
