Had Sean Connery taken the lucrative deal that was presented to him in 1999 by New Line Cinema to play Gandalf the Grey in Peter Jackson's Lord of the Rings trilogy, he could have cleared up to as much as $434 million. Connery's squandered opportunity is the subject of a story in today's edition of The Scotsman, which gleaned the information from a passage in Brian Sibley's recent biography of Jackson. According to the piece, New Line was so worried about staking the Rings threesome without a single major, international star attached that they crafted for Connery a lavish backend deal similar to the one that lured Nicholson to play The Joker in 1989's Batman. Peter Jackson is quoted as saying that Rings executive producer Mark Ordesky told him "NewLine was prepared to give him [Connery] between 10 percent and 15 percent of the films' income." Had that happened, Connery would have cashed more scratch for a single project than any actor in history.
The famously prickly Connery has gone on record saying that he wouldn't have taken the role of the big-hatted wizard because "I never understood it. I read the book, I read the script, I saw the movie, and I still don't understand it." The book also implies that Jackson wasn't keen on casting Connery, either. "I couldn't imagine him wanting to spend eighteen months in New Zealand," Jackson says, which sounds like polite movie-talk for "Please don't come and spend eighteen months in New Zealand." I personally could see Connery as a quiet, reflective Obi-Wan type, but anyone who remembers The Rock knows how silly he looks with long hair, so his interpretation of Gandalf might not have gone over well.