Frank Sinatra Was Almost an Action Star!
Stallone, Schwarzenegger … Sinatra? When we think of Frank Sinatra as an actor, most of us summon up his harrowing performance in The Man With the Golden Arm, his Oscar-winning turn in From Here to Eternity or his slick Danny Ocean in the 1960 classic Ocean’s 11. But Sinatra actually had not one, but two moments in his career when he almost joined the ranks of legendary Hollywood action heroes. Alas, he passed on both opportunities, so we’ll never know how the Chairman of the Board would have looked asking a criminal if he feels lucky, punk.
In a 2015 episode of Alec Baldwin‘s podcast, Here’s the Thing, William Friedkin — the groundbreaking and Academy Award-winning director behind The Exorcist and The French Connection — told of his original plan to direct Dirty Harry, with Sinatra as the titular cop. “We were going to do Dirty Harry with Frank Sinatra,” Friedkin recalled. “We had prepared that for about six months and then Sinatra pulled out. The project was dead. We left and did The French Connection.”
Everett Collection
Though neither Friedkin or Sinatra ever publicly commented on why Sinatra left the project, Hollywood rumor has long suggested it was because of a hand injury Sinatra suffered on the set of The Manchurian Candidate, which made holding large prop guns uncomfortable. In 1971, Dirty Harry was released, with Clint Eastwood as Harry Callahan — a role that would come to be one of his most iconic. In a 2008 interview, Eastwood told MTV.com this about Sinatra’s involvement in the film:
I guess they tried to get a lot of people for it. They tried Frank Sinatra and Robert Mitchum and Steve McQueen. Then they finally ended up with Frank Sinatra. I was in postproduction [on ‘Play Misty for Me’], and they called up and asked, “Are you still interested in ‘Dirty Harry’?” I said, “What happened to Frank Sinatra?” And they said, “Frank Sinatra’s got some problem with his hand and he can’t hold a gun.” That sounded like a pretty lame excuse, but it didn’t matter to me. I said, “I’ll do it.”
Sinatra as a tough guy taking on a serial killer in gritty 1970s San Francisco isn’t necessarily too difficult to picture. But Ol’ Blue Eyes crawling through the air ducts at Nakatomi Plaza? That takes some imagination.
And yet, it almost did happen … sort of.
20th Century Fox Film Corp./courtesy Everett Collection
To understand how Frank Sinatra was offered the role of John McClane in 1988’s Die Hard takes some backstory. As any Sinatra devotee will recall, Sinatra starred in 1968’s The Detective (pictured above) as no-nonsense New York City cop John Leland (Mia Farrow fans will also recall that Farrow’s refusal to leave the set of Rosemary’s Baby in order to costar in The Detective occasioned Sinatra ending their marriage). The Detective was based on the 1966 novel of the same name by writer Roderick Thorp.
In 1979, Thorp penned a sequel to The Detective, again focusing on detective John Leland, called Nothing Lasts Forever. But in this volume, Leland has traveled to Los Angeles for Christmas and is drawn into a situation where a group of international terrorists attacks an office Christmas party. Yup, Nothing Lasts Forever was adapted into Die Hard. Given his appearance in The Detective, Sinatra had the right of first refusal for the role — but since he was over 70 years old at the time, the offer was probably not too tempting. After he passed, Richard Gere, Mel Gibson, Harrison Ford, Sylvester Stallone, Arnold Schwarzenegger and Burt Reynolds were all considered, before Bruce Willis finally landed the role and yippee ki-yay-ed his way to cinematic superstardom.
It’s tough to imagine either of these roles without the actors who ended up in them, so perhaps it’s a good thing that Sinatra passed … though the idea of John McClane killing Hans Gruber while looking sharp in a three-piece suit and not spilling a drop of his martini is an intriguing one. Potential reboot, anyone?
Remind 
Classic Hollywood Hunks
September 2019
Cary Grant, Sean Connery, Rock Hudson and Paul Newman, smoldered onscreen and, in addition to being smokin’ hot, they were effortlessly cool.
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