Sean Connery was truly a legend of an actor. He originated James Bond in the feature films, and did it so well that, for many, no others held up to his performance of the sexy British spy. His Bond films are among his most beloved, but he also played a Russian defector in The Hunt for Red October, a bumbling Henry Jones Sr. in The Last Crusade, an Alcatraz escapee in The Rock, and many more.
But there were many roles he missed out on, too. And some he was probably not well suited for, if we're honest, mostly because the people who did end up in the parts went on to make them iconic, and imagining Connery there instead is… well, just a little weird. Like, I just can't see him as Gandalf the Grey, despite how much I enjoy him as an actor.
But he still openly regretted passing on several of those roles, which is what we're going to examine today.
'Live and Let Die' Credit: Amazon MGM
James Bond, Live and Let Die
Bond made him, but eventually, Connery decided to leave the franchise.
Screen Rant reports he turned down a $5.5 million offer to return for Live and Let Die, telling the screenwriter his obligation to the character had to end at some point. He made The Offence instead, the first film under his United Artists deal.
Diamonds Are Forever was Sean Connery's last time playing the part in the official series, but he returned one last time for Never Say Never Again in 1983. The film is not considered Bond canon because it was produced by Taliafilm and Kevin McClory rather than Eon Productions (the result of a story credit dispute between Ian Fleming, McClory, and Jack Whittingham).
His wife, Micheline Roquebrune, suggested the film's title because of Connery's initial promise to never return to Bond.
Sybok, Star Trek V: The Final Frontier
William Shatner wanted Connery, knowing his involvement could boost the film's overseas box office. He was offered the part of Sybok, Mr. Spock's older half-brother.
But before Paramount could close the deal, Connery took Indiana Jones and the Last Crusade, which was filming at the same time (per Screen Rant). Laurence Luckinbill ended up in the part instead.
Even though Connery turned down the part, the name of the mythical paradise at the center of the galaxy—Sha Ka Ree—was kept as an intentional phonetic nod to "Sean Connery" (via Memory Alpha).
John Hammond, Jurassic Park
Steven Spielberg and Connery had obviously worked together on Indiana Jones, where Connery played Indiana's father. Novelist Michael Crichton had also worked with Connery on The First Great Train Robbery. So it makes sense that Connery, with his Scottish accent, was considered for the role of wealthy park owner John Hammond.
Rumors have it that Connery's fee was too high, so Richard Attenborough got the role instead. According to the New York Daily News, Harrison Ford also passed on Dr. Alan Grant, so Sam Neill stepped up.
'Jurassic Park' Credit: Universal Pictures
Simon Gruber, Die Hard with a Vengeance
John McTiernan, who had directed Connery in The Hunt for Red October and Medicine Man, wanted him first for the part of this villain, per Yahoo. But Connery didn't want to play a villain, so Jeremy Irons got the part. Simon is Hans Gruber's older brother, the villain from the original Die Hard.
Connery played a heavy a few years later, in The Avengers. He also took on The Rock, where he played an anti-hero who broke out of Alcatraz.
Gandalf, The Lord of the Rings
Most people know this one, and it's wild to think about. Connery was offered the role of the powerful Middle-earth wizard in The Fellowship of the Ring.
Ian McKellen, who became the wizard we all know and love, spoke to The Independent about his casting.
"They only wanted me because the established stars said no," McKellen said. "They wanted Tony Hopkins and Sean Connery."
New Line Cinema executive Mark Ordesky told the outlet, "We did make an offer to Connery, but he said no. We never got an answer until years later, but apparently he read the material and just didn't get it."
Later, Peter Jackson told Empire:
"Look, I'm only speculating, but I just can't imagine Sean Connery being as supportive as Ian McKellen was, and being as willing to do whatever we wanted as Ian was, and being as tolerant as Ian was. And there were the tee times to consider."
'The Matrix' Credit: Warner Bros.
Morpheus, The Matrix
Which role he passed on is debated, but CBR says Morpheus is the generally assumed offer, with an unconfirmed pass on the Architect for Reloaded.
Later, Connery accepted The League of Extraordinary Gentlemen. In behind-the-scenes footage for the film, producer Don Murphy recalls a conversation between Connery and director Stephen Norrington.
"In his kind of teasing way, he said, 'You know, they offered me The Matrix, and I didn't understand it, so I turned it down. And they offered me The Lord of the Rings, and I didn't understand it, so I turned it down. And I'm not sure I understand this, but I'm not gonna turn it down.'"
Albus Dumbledore, Harry Potter and the Sorcerer's Stone
Turns out Gandalf wasn't the only wizard Connery passed on. Director Chris Columbus looked at Connery to play Hogwarts headmaster Albus Dumbledore even before Richard Harris, per Deccan Herald.
Collider says Connery's reasons for passing aren't clear, but he didn't have a great experience on The League of Extraordinary Gentlemen, which many point to as the reason he decided to step away from acting, per The Irish Star.
The Scotsman reported the friction Connery had with Norrington on set.
At the time, Connery said, "But my philosophy has been to shoot the movie and talk about right and wrong afterwards. To be honest, I just want to complete the picture. That's all I want right now."
He officially retired from acting in 2003, but the Extraordinary Gentlemen timeline would have coincided with his stepping away, so perhaps he was truly just done with Hollywood when Harry Potter came around. Extraordinary Gentlemen was his final on-screen appearance. He died on October 31, 2020.
