Both Clint Eastwood and Frank Sinatra are both celebrities who openly involved themselves in helping political candidates they liked.
And that’s pretty much where their similarities end.
But now it’s come out that Eastwood’s career would have looked very differently had Sinatra accepted this iconic role.
Strangers in the Night, Clint Eastwood and Frank Sinatra
Frank Sinatra is obviously known for his crooning that took him to the top of the music charts.
However, he was no stranger to the big screen.
Old Blue Eyes starred in dozens of movies spanning several different genres.
Sinatra could aptly ply his craft in anything from war drama to crime comedies.
Ocean’s Eleven might be the role he’s most known for, while he won awards for From Here to Eternity, and many critics agree he was at his best in The Manchurian Candidate.
And while the leader of the Rat Pack was the total package as an entertainer, most would agree his acting chops don’t measure up to the likes of Clint Eastwood.
Eastwood has enjoyed one of the most star-studded careers in cinematic history.
While his behind-the-scenes contributions are vast and varied, there’s a particular character type on-screen that has made him famous.
Perhaps no one can match the former mayor of Carmel-by-the-Sea, California when it comes to portraying a tough, no-nonsense, gritty, actions-speak-louder-than-words, hero.
When thinking about Eastwood’s performances, names like Unforgiven’s William Munny, Gran Torino’s Walt Kowalski, and of course, The Man with No Name from the Dollars Trilogy are likely to instantly pop to mind.,
Then there’s the very quotable – as long as you’re not in mixed company – Harry Callahan of Dirty Harry fame.
Dirty Frank?
However, interviews from the participating parties show that Eastwood almost missed out on the iconic role all the way back in 1971.
The part of cop Harry Callahan was, in fact, originally intended for not Eastwood, but none other than Paul Newman.
According to Far Out Magazine, out of the United Kingdom, the movie was originally titled, “Dead Right,” and was written with Newman in mind for the lead.
Fresh on the heels of hits like Cool Hand Luke and Butch Cassidy and the Sundance Kid, one can easily understand why writers Harry and Rita Fink believed Newman was perfect to play Callahan.
However, Far Out Magazine reported that the very political Newman decided to pass on the part, believing it to be “too Right-wing.”
The name of the film eventually morphed into “Callahan,” and the starring role was awarded to Sinatra.
In an interview at the time, Sinatra revealed that the motion picture would be shooting in San Francisco for eight weeks.
And he was clearly excited about the script.
“It’s a marvelous script,” Sinatra said. “It’s a darn good script, it really is. Great suspense.”
However, Sinatra pulled out of the project, and according to Far Out Magazine, there is a conflict over the reason.
Publicly Sinatra said it was because he broke his wrist while filming The Manchurian Candidate.
But Eastwood’s biographer, Marc Eliot, has a different account.
Eliot believes Sinatra backed out due to reservations about playing “such an unsympathetic character.”
Once Newman and Sinatra were both out, only then did filmmaker Donald Siegel turn to Eastwood.
The name of the flick changed once again, this time to Dirty Harry, and the rest, as they say, is history.
While it’s intriguing to think of how different the movie would have played out with Newman or Sinatra in the title role, Eastwood turned out to be the perfect fit for the Callahan character.
The movie was such a resounding hit, and Eastwood was so good in it, that it spawned four sequels, Magnum Force, The Enforcer, Sudden Impact – which Eastwood also directed – and The Dead Pool.
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