This 1940s singer might not be the man who
comes to mind when you think about the action-packed
Die Hard movies.
At the start of his movie-making career, Sinatra
was cast mostly in singing roles, though he
did manage to break away from being a “singer
employed as an actor” and made a name for
himself as an actor alone, winning a few Academy
Awards and Golden Globes for his performances.
That said, many people these days can’t
shake that image of young Sinatra crooning
into a microphone—not exactly something
you’d imagine the character of John McClane
doing.
So, how did Frank come to be considered for
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.
The movie, of course, did extremely well,
with a budget of just $28 million, the film
grossed about $140 million by the time it
was out of theatres (about $268 million today),
earned four Academy Award nominations, and
was generally well-received by critics.
The franchise of Die Hard is still going strong,
though its original writer and main character
have since passed away.
Sinatra died in 1998 at the age of 82, while
Thorp passed away in 1999 at the age of 62.
Willis, meanwhile, had his career made by
the Die Hard movies and despite now getting
up there in years himself (about to turn 59
) remains involved in 
the series as well as other action movies.
