Frank Sinatra played Detective Joe Leland from the novel "The Detective" by Roderick Thorp. Thorp wrote a sequel ("Nothing Lasts Forever") in which Leland is trapped in a Claxxon Oil Corporation skyscraper after it's taken by German terrorists, and must rescue his daughter and grandchildren. Twenty years later the novel was filmed with some changes: the daughter became his wife, Claxxon became the Nakatomi Corporation, and Joe Leland's name was changed to John McClane. The film was released under the title Die Hard (1988). Because of a clause in Sinatra's contract for "The Detective", which gave him the right to reprise his role in a sequel, he was actually the first person offered the McClane role, even though he was seventy-three-years-old at the time. Also, coincidentally, Bruce Willis (who played McClane) made his movie debut in The First Deadly Sin (1980) walking out of a bar as Sinatra walked into it. Additionally, Lloyd Bochner played Dr. Wendell Roberts in this movie. His son, Hart Bochner, played Harry Ellis in Die Hard (1988).
Frank Sinatra was supposed to co-star with his wife Mia Farrow in this film, but a film Farrow was working on was running behind schedule, so she refused. Sinatra got so mad, he made the film without her (casting Jacqueline Bisset in the role instead) and served her divorce papers on the set of that film, Rosemary's Baby (1968).
Robert Evans had acquired the rights to "The Detective" and was supposed to produce the movie for 20th Century Fox, which had signed him to a contract (he had earlier worked for Fox as an actor). When Charlie Bluhdorn, the owner of Paramount Pictures, offered Evans a job as the head of European production at Paramount Pictures, Evans had to surrender the project to get out of his Fox contract.