From 'The Detective' to 'Die Hard': Sinatra’s Unused Role in Hollywood Classic
How contractual obligations led Sinatra to turn down Die Hard.
In the original casting process for Die Hard, the role ultimately played by Bruce Willis was initially offered to none other than Frank Sinatra, who was then 73 years old.
Sinatra was contractually entitled to be considered first because he starred in the film’s prequel back in 1968. That earlier film, The Detective, was based on a novel, and Sinatra’s performance in it made him the star of that adaptation. Over ten years later, a new book was published as a sequel to the original story, which served as the inspiration for the 1988 blockbuster Die Hard. This connection meant that, technically, Die Hard was a sequel to Sinatra’s The Detective. Due to contractual obligations stemming from his previous role, Sinatra had the right of first refusal for the part.
However, at 73 years old, Sinatra graciously declined the offer, recognising that he was no longer suited for such an action-packed role. His decision opened the door for Bruce Willis to take on what would become one of his most iconic roles. This fascinating piece of Hollywood history highlights how contractual ties and age can influence casting decisions, even decades after an actor’s initial appearance.
