Answer: Frank Sinatra

The producers of 1988 action film Die Hard cast Bruce Willis in the role of John McClane, but not before first offering the role to Frank Sinatra. Given that Sinatra was in his early 70s at the time, it seems more than a bit counter-intuitive that they’d offer him the role of a young detective who takes on a team of highly organised criminals and their mastermind leader.

Why offer the role to Sinatra? Let’s take a long walk through the legal department while we explain. Die Hard is based on the book Nothing Lasts Forever by Roderick Thorp. The novel is a sequel to Thorp’s 1966 novel The Detective which was made into a movie with the same name in 1968 starring, you guessed it, Frank Sinatra. 20th Century Fox was contractually obligated to offer Frank Sinatra the ability to reprise his role in the film adaptation of Thorp’s literary universe even though the chances of him actually taking the role were slim.

When Sinatra turned the role down, they didn’t immediately turn to Willis though. The movie studio instead pitched it to Arnold Schwarzenegger as a sequel to the 1985 action film Commando. When that pitch was turned down, they continued to shop the script around, pitching it to well known action movie stars around Hollywood. Eventually Willis was offered the role despite his lack of experience in the action movie genre. Despite that lack of experience, the film went on to be a box office success and is now hailed as one of the greatest action movies ever made.