When you think of the most epic Hollywood mistakes of all time, a few stories stand out. For example, did you know that Will Smith turned down the part of Neo in "The Matrix"? Or that James Cameron originally offered the role of the Terminator to OJ Simpson before settling on Arnold Schwarzenegger? In Hollywood, careers can be launched or broken by one bad decision, and, in the process, vast fortunes can be made or thrown away. Even a veteran star like Sean Connery can make a mistake so big that it ultimately causes him to retire from acting and lose out on a mind-blowing amount of money. That's exactly what happened when Connery turned down the role of Gandalf in "Lord of the Rings"…
Before "Lord of the Rings" became a massive worldwide success, it was seen as a VERY risky undertaking for Time Warner's movie studio, New Line Cinema. With a budget of $281 million, the films were the most expensive movies of all time to that point. In an unprecedented move, all three movies were filmed back to back in New Zealand by a relatively unknown director named Peter Jackson. The movie also lacked a truly big Hollywood name like Tom Cruise or Johnny Depp that would guarantee ticket sales. For all these reasons, the producers desperately wanted to lock in a huge star for the crucial role of Gandalf. Their first choice was Mr. James Bond himself, Sean Connery.
In order to convince Connery to sign on to the film, the producers pulled out all the stops. In addition to a $10 million per film salary, they offered Connery 15% of the box office for all three movies.
In what would turn out to be a monumentally poor decision, Connery declined the part because he "did not understand the script".
To be fair, if I had read the LOTR script, I probably would have thought it was absolutely ridiculous and would be a huge bust. Well, as we all know now, Lord of The Rings went on to become one of the highest-grossing film franchises of all time.
The first movie alone is the sixth highest-earning film in history, with over $1 billion in ticket sales. The combined box office totals for the first three films would eventually balloon to $2.9 billion.
As for Sean Connery, his 15% stake would have been worth $450 million. That would have been the biggest single payday any actor has ever received.
(Photo by Frazer Harrison/Getty Images for AFI)
Not that Sean Connery is struggling financially; he still had a net worth of $350 million at the time of his death in October 2020, but that $450 million loss couldn't have been an easy pill to swallow.
In reaction to LOTR's huge success, Connery hastily agreed to appear in 2003's "The League of Extraordinary Gentlemen," which he hoped would become an equally big success and franchise. Unfortunately, "The League of Extraordinary Gentlemen" was a flop, earning just $66 million worldwide off a budget of $78 million. This failure, likely coupled with the knowledge that he let nearly a half billion dollars slip through his fingers, was too much to handle, and Sean Connery retired from acting completely in 2005.
Read more: The Story Of How Sean Connery Gave Up $450 Million By Turning Down "Lord of The Rings"
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