Sean Connery is a titan of cinema. He's been around for a long time, portraying both memorable and rather forgettable characters. But there are a number of roles Sean Connery could've played that would have made his career that much richer. They weren't little parts, either. Rejected Sean Connery roles have gone to such megastars as Ian McKellen, Michael Caine, and Richard Harris, to name a few.
Sure, Connery sometimes had a good excuse for saying no, like playing a certain super spy in blockbuster movies in lieu of being the millionth Tarzan to swing from that vine. But that doesn't mean Connery's above making questionable career decisions. He played Allan Quatermain in the widely panned flick The League of Extraordinary Gentlemen, right around the time he passed on parts in The Lord of the Rings and The Matrix. His agent probably wasn't jazzed about those decisions.
Some of the roles Sean Connery turned down might have led to regret; other choices likely worked out better for the final product. But there's no denying that the actor's growling Scottish voice and unique swagger would have brought something different to every character.
Gandalf might be Ian McKellen's most famous role, but it almost belonged to Connery. He said no, despite being offered a whopping $6 million per film. But he doesn't seem to regret it, saying, "I read the book. I read the script. I saw the movie. I still don’t understand it. Ian McKellen, I believe, is marvelous in it."
Alan Trustman, the screenwriter of the original The Thomas Crown Affair, wrote the lead role with Connery specifically in mind. But the actor said no, and the character was ultimately played by Steve McQueen.
Connery passed on the role of Simon Gruber in Die Hard with a Vengeance because he didn't want to play such an evil character. Jeremy Irons got the part.
Connery was offered two roles in The Matrix series: first Morpheus, and then the Architect. He turned them both down because he didn't understand the script. The parts went to Laurence Fishburne and Helmut Bakaitis, respectively.