Legendary singer Frank Sinatra almost played the main character, John McClane, in Die Hard. Sinatra was the first choice due to a contractual obligation, due to a previous film he starred in. That film was ‘The Detective’, a movie based on Roderick Thorp’s 1966 novel of the same name. Die Hard was based on the sequel of that book, ‘Nothing Lasts Forever’. As Sinatra played the main character in the adaption of the first book, he had to be offered the role in the second. Thankfully, he declined.