When you think about who could’ve pulled off playing John McClane in 1988’s Die Hard other than Bruce Willis, what kind of names pop into your head? Action stars like Arnold Schwarzenegger, Sylvester Stallone, Burt Reynolds, and Harrison Ford probably spring to mind, no? It should come as no surprise, then, that every single one of those actors was offered Willis’s role at some point. You know what is surprising, though? The first person the filmmakers reached out to about starring in the movie was Frank Sinatra.

Here’s how that ended up happening: Die Hard, as it turns out, is actually based on the 1979 Roderick Thorp novel Nothing Lasts Forever. The story revolves around retired NYPD detective Joseph Leland, who heads to Los Angeles to visit his estranged daughter, Stephanie Gennaro. Stephanie works inside a 40-story skyscraper, where her company is throwing its annual Christmas party.

While Leland waits for the party to end, a group of terrorists take the guests hostage, forcing Leland to spring into action.

‘Die Hard’ Had to Offer John McClane to Frank Sinatra First

But Nothing Lasts Forever wasn’t the first book to feature Leland. The ex-cop made his literary debut in Thorp’s 1966 novel The Detective. Two years later, The Detective was adapted into a film in which Leland was portrayed by none other than Frank Sinatra. Though the movie did well both critically and commercially, the idea of a sequel didn’t come about until after Thorp wrote Nothing Lasts Forever.

However, the folks at 20th Century Fox were evidently pleased enough with The Detective that they purchased the rights to a follow-up long before one had even been written. Because of that, the studio was contractually obligated to offer Sinatra the lead role in Die Hard. To clarify how ridiculous it would’ve been for Sinatra to entertain the possibility of taking the job, the singer was 77 years old by the time Die Hard was released. Sinatra wisely declined the proposal.

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