Before Sir Ian McKellen took the role of Gandalf in the Lord of the Rings trilogy, Sir Sean Connery was sought for the part. New Line Cinema even offered him 10 to 15 percent of the worldwide box office earnings to get him aboard. However, Sean Connery declined the offer because he didn’t understand the story.
New Line were indicating that having a major name like Connery was necessary in order for them to green-light the film. They asked us if we would agree to send a copy of the Fellowship screenplay to Sean with a view to enticing him to play Gandalf.
I couldn’t imagine him wanting to spend eighteen months in New Zealand, and I didn’t think they could afford his fee, but [Mark] Ordesky [the film's executive producer] told me New Line were going to offer a small fee in exchange for a large slice of the gross.
Had Sean Connery accepted, he would have earned anywhere between $289 million and $433 million which would have gone down in history as the highest earnings from a single screen role than any actor has made in the history of motion pictures.
They say they don’t think Sean Connery regrets not taking the role. I would say this regret ranks right up there with not using a condom on that $5 hooker and punching Mike Tyson in the face.