Frank Sinatra Almost Became an 80s Action Hero

Steve Palace
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Believe it or not, there was a time when Frank Sinatra was wanted for the lead role in Die Hard.

How had this happened? When the movie was in production, Bruce Willis’s reputation was somewhat different to what it is now.

A 2014 Business Insider article wrote that “Willis was not exactly the kind of person the studio was hoping to cast in the role.”

Frank Sinatra

In the late Eighties he was best known for the romantic comedy TV show Moonlighting and Blake Edwards’ movie romp Blind Date. He was affable yes, resourceful, kind of tough… but an action hero? Forget it.

Of course naysayers went on to eat their words. With Willis at its heart the film was a smash hit. Its self-contained, high concept premise of a skyscraper under siege made it dynamic and innovative. Put-upon central character John McLane became the most enduring part of his career to date.

Bruce Willis in 2010. Photo by Gage Skidmore CC BY-SA 3.0

Based on the 1979 book Nothing Lasts Forever by Roderick Thorp, the original flick took some time to reach the screen. And when producers were first mulling over a movie version, Sinatra’s name was top of the list.

While this sounds strange, it makes sense in the context of the source novel. Nothing Lasts Forever was thought of by Thorp in a dream. He’d somehow managed to go to sleep during that other iconic skyscraper film, The Towering Inferno (1974).

Bruce Willis running with automatic weapon in a scene from the film ‘Die Hard’, 1988. Photo by 20th Century-Fox/Getty Images

He wound up dreaming about Joe Leland, the hero of his previous book The Detective (1966), facing off against criminals in a high rise. This was the essence of Nothing Lasts Forever, a follow up to Leland’s debut story.

The Detective had been filmed in 1968, starring none other than “Ol’ Blue Eyes.” This gritty police thriller, which tackled sensitive topics such as homosexuality, was a high point on Sinatra’s CV.

Frank Sinatra in 1955.

His acting chops were tested in this and other movies like The Man With The Golden Arm (1955), The Manchurian Candidate (1962) and Von Ryan’s Express (1965).

A major factor that prevented Sinatra’s involvement was time. Die Hard began to take shape 2 decades after The Detective, and while Joe Leland had reached retirement age in the novel, the smooth crooner himself was way past that. At 73 he just wouldn’t have cut it.

Photo of Frank Sinatra and Lee Remick from the film ‘The Detective’.

Whether he’d have been required to run around in a vest, crawl through ventilation shafts and use foul language is unclear. Plus accounts of why exactly the Sinatra version didn’t happen vary.

Business Insider claimed that “Because the movie was technically a sequel, they were contractually obligated to offer Frank Sinatra the leading role. He was 73 years old at the time and gracefully turned the offer down.”

The Independent says “Producers had hoped Sinatra would return as Leland for the sequel.” Either way, the swinging “Chairman of the Board” put the brakes on.

Sinatra as Tony Rome.

Joe Leland switched his name to John McLane. Arnold Schwarzenegger was approached, in what might surely have been the most radical actor replacement in film history. Finally, Willis got the gig. It’s difficult to imagine anyone else in the part.

Die Hard celebrates its 30th anniversary this year. A piece in The Independent refers to it being “nothing short of a phenomenon, spawning four sequels to date and a loyal fan base, many of whom claim it as their favourite Christmas film.”

Yes, the mayhem occurs during the holiday season. The most wonderful time of the year is also the most explosive and swear-laden.

Read another story from us: The FBI Files and Mob Ties of Frank Sinatra

A Die Hard with Frank Sinatra would have been an unusual affair. Yet the prospect of him asking Alan Rickman’s Hans Gruber to “Come fly with me” before his death plunge is an entertaining idea indeed!