Fans of the Christmas film (controversial) Die Hard were astonished after learning that a legendary singer was originally in line to star in it. Bruce Willis famously took on the role of John McClane, the iconic action figure who hunted down terrorists in Nakatomi Plaza.

Despite Willis’ success and his return for four more instalments of the much-loved franchise directed by John McTiernan, he wasn’t the first pick for the character. Hollywood greats like Harrison Ford and Sylvester Stallone opted not to become McClane.

James Caan, known for The Godfather and Thief, along with Arnold Schwarzenegger and Clint Eastwood, also refused the part. Yet, none of these big names were the studio’s initial selection due to an outstanding contract with the renowned balladeer Frank Sinatra.

The contract, which was put in place in 1968, meant 20th Century Fox were obligated to offer the role to legendary singer Frank Sinatra. Best known for his covers of My Way and Fly Me to the Moon, Sinatra had starred in the Die Hard prequel, The Detective. As part of his contract at the time, Sinatra was to be offered a sequel project should it come to light.

But a sequel was not written until years after The Detective had released, meaning Sinatra was 70 by the time Die Hard entered production. Honouring their contract, 20th Century Fox still offered Sinatra the role as John McClanem, but he declined. Fans have since had their minds blown by what could have been, and say a Sinatra-starring Die Hard would be “amazing”.

One user took to Twitter/X and wrote: “Omg that would have been amazing. Massive shootout denouement as Sinatra blows away goons left right and centre to the crescendoing finale of My Way. I mean can you not HEAR the final ‘MYYYYY WAYYYYY’ playing your head over Alan Rickman’s final slow motion plummet?”

Another wrote: “I am still trying to adjust to discovering a Die Hard prequel exists starring Frank Sinatra in a gritty, realistic look at the dark corners of police work.” The Detective, released in 1968, is an adaptation of the Roderick Thorp book of the same name. It was not until 1979 that Thorp wrote a sequel, titled Nothing Lasts Forever. It was later turned into Die Hard as 20th Century Fox had bought the rights before it had even been written.

But doing so meant they had to offer Sinatra the chance to reprise his character Joe Leland, renamed John McClane in Die Hard and the films to follow. Film buffs have since shared why Sinatra was offered the chance to return to the series, despite his age.

One wrote: “The movie [The Detective] was a hit and Sinatra wanted a sequel. However the author of the novel on which the film was based Roderick Thorp didn’t release a sequel until a decade later.” Another wrote: “Younger Sinatra probably could have pulled off Die Hard though.”

A third joked a Sinatra-starring Die Hard would have been a perfect play for a Rat Pack reunion. The group, which featured Sammy Davis Jr., Dean Martin and Sinatra, was an informal group which often made concert appearances and films together. One fan wrote: “Sammy Davis Jr. as Sgt. Powell and Dean Martin playing Hans Gruber. Top notch.”

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