So, how did Frank come to be offered the role? It all started with an author named Roderick Thorp. You might not know it, but the Die Hard movie was based on a book called Nothing Lasts Forever by Thorp, which was published in 1979. The LA Times reviewed the book, saying it was “A ferocious, bloody, raging book so single-mindedly brilliant in concept and execution that it should be read at a single sitting.” This book is really what made Thorp a big name, but he was on the publishing scene much earlier.
It turns out that Nothing Lasts Forever is actually a sequel to a book called The Detective, published in 1966 which was made into a movie of the same name in 1968. The movie starred—you guessed it—Frank Sinatra as the main character, Detective Joe Leland. The book was extremely popular, remaining on bestseller lists for a while and making a name for Thorp; the movie also did well in the box office. It was described as “gritty” for its time, dealing with issues like homosexuality, but it was decidedly less action-packed than the Die Hard movies we know today.
Die Hard itself wasn’t picked up by producers until 1988, nearly 10 years after the book it was based on was published. 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.
After Sinatra turned the offer down, the role was offered to Arnold Schwarzenegger, and the movie was pitched as a sequel to the actor’s 1985 film Commando rather than a sequel to The Detective. Schwarzenegger also turned down the offer, and instead Bruce Willis was cast in the leading role, with the character renamed John McClane instead of Joe Leland.
Willis was not exactly the kind of person the studio was hoping to cast in the role. At the time, he was mostly only known for comedies, not action movies. But they had been turned down by a variety of other actors since offering the role to Sinatra and Schwarzenegger, and they had to settle.
via Today I Found Out.