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

Die Hard is an unquestioned action masterpiece. Thanks to revelatory performances by both Bruce Willis and Alan Rickman, plus John McTiernan’s assured direction, Die Hard still has the power to awe and entertain even decades after its release. Few can say the same about the sequels, but what about the Die Hard prequel, The Detective?

Oh, you’ve never heard of a Die Hard prequel? Well, that could be because the 1968 Frank Sinatra vehicle The Detective is based on the 1966 novel by the same name, written by Roderick Thorp. And in 1979, Thorp published a sequel to The Detective called Nothing Lasts Forever, in which criminals led by a man called Gruber take control of a Los Angeles high-rise during a company party. Gruber even holds hostage the family member of a hero cop who must go rogue upstairs if he is going to thwart the terrorists. Also it’s Christmas time.

As you guessed, Nothing Lasts Forever inspired Die Hard, with a few notable revisions, including changing the protagonist’s name from Joe Leland to John McClane—but only after Sinatra passed on Die Hard. But even with those changes to the Die Hard script, The Detective still provides a glimpse of McClane’s days as a New York cop before his fateful day at Nakatomi Plaza.

The Early Adventures of John McClane Joe Leland

“I’m a New York cop,” John McClane tells affable limo driver Argyle at the start of Die Hard. “With a six-month backlog of New York scumbags I’m still trying to put behind bars.” He says the line with tired resignation, something that goes deeper than the marital problems he’s outlining to the extremely nosy driver.

In The Detective, we get a glimpse at who those scumbags might be. And it’s easy to see why the experience would weigh so heavily on him. The movie begins with Leland arriving at a crime scene where he’s initially greeted by young Detective Robbie Loughlin (Al Freeman Jr.).

“I hear you’re the best detective in town,” he enthuses, to which Leland only flashes a proud smile.

That smile disappears immediately, never again to return, when Joe and Robbie find the body of a mutilated man with his head caved in. Things only get bleaker from there, as the script by Abby Mann takes Leland and his partner Dave Schoenstein (Jack Klugman) through a sordid tale of corruption, dealing with the horrible decisions by a powerful closeted man.

At first glance, The Detective only has the barest of connections to Die Hard. In his early 50s, Sinatra carries a weight missing from twenty-years-younger Willis. To that point, Leland spends more time doing actual detective work, befitting the movie’s tagline: “An adult look at police work,” and never crawls through a single air duct. Not even once.

And yet, the similarities are there. Sinatra’s Leland relies on help from his allies Schoenstein, Loughlin, and others, foreshadowing the way McClane will get help from Al Powell (Reginald VelJohnson) in Die Hard. Most notably, Lee’s screenplay emphasizes the breakdown between Leland and his wife Karen (no, not Holly, but played by future The Omen star Lee Remick), flashing back to the happy couple’s life before that backlog of New York scumbags sabotaged that relationship.

From Nothing Lasts Forever to Die Hard

The above description may lead you to think that Nothing Lasts Forever has only the barest of connections to Die Hard. After all, Nothing Lasts Forever released in 1979, a full 13 years after The Detective. How could the now-retired Leland do anything similar to McClane’s feats in Die Hard?

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.