Frank Sinatra Starred in the Die Hard Prequel You Probably Never Saw

But believe it or not, a lot of Nothing Lasts Forever makes it into the movie. The book finds Leland coming from New York to Los Angeles at Christmastime to visit a family member when he’s caught in the middle of a terrorist siege of the tower where that family member works. Leland battles against terrorist leader Gruber, relying on help on the outside from Sgt. Al Powell. Heck, Leland even makes a barefoot escape across broken glass and swings C4 to a lower part of the building. And yes, coke-fiend Harry Ellis appears in the book, trying to be Gruber’s white knight.

Of course Die Hard does make some cosmetic changes to this plot. It’s his daughter Stephanie Gennaro whom Leland comes to visit in the book. Worse still, she has become a drug abuser thanks to her affair with Ellis. The action takes place in the Klaxon Oil Tower, and Klaxon president Mr. Rivers dies after refusing to give Gruber the safe codes. Finally, it is Anton Gruber who leads the siege of the tower, and his goals are more straightforward. Instead of hiding a straightforward heist under political rhetoric, Anton Gruber—nicknamed Little Tony the Red—blames Klaxon for the death of his own daughter.

But while the original Die Hard screenwriter Jeb Stuart held onto much of the novel’s basic plot, he significantly changed the tone, which became even punchier and more fun with rewrites by Steven E. de Souza. Gone are the hardboiled meditations of the novels, which did find their way into the Sinatra film. They’re instead replaced by a cowboy motif emphasized by Stuart. Most notably, Stuart removes the original ending, in which Gruber drags Stephanie down with him, and they both fall from the tower to their deaths.

Frank Sinatra Stars as John McClane in Die Hard

Most people know that Willis was far from the first choice to play McClane, having risen to stardom on the romantic comedy/drama tv show Moonlighting. But fewer people know the first choice to star in Die Hard was Frank Sinatra.

Okay, that’s not entirely true. Sinatra had a clause in his contract that gave him the right of first refusal for all sequels to The Detective, and even with Stuart’s changes, that included Die Hard. And while Joe Leland is quite a bit older in Nothing Lasts Forever, even Sinatra realized that he would be a bad fit at 70 years old for running around barefoot with a machine gun. Still, he was offered the part as was his right, and turned it down. Afterward, rather than go directly to someone like Willis, the studio originally looked for older actors to play the more weathered hero, including Paul Newman, James Caan, and Al Pacino. With one of these guys in the lead, Die Hard would have certainly hewed much more to the dour tone of the original novel.

Of course, that’s not what happened. Willis got the part, Die Hard became a fun action movie, and the rest is history. In fact, it’s been almost 30 years to the day since Die Hard‘s release. Still, The Detective helps us see a bit of the weariness that weighed on the central character, even after he went from Joe Leland to Bruce Willis.