Sean Connery wasn’t supposed to be James Bond. Keanu wasn’t supposed to be “the One.” So, who were the original choices? Here are 5 actors and the legendary roles they turned down.

THE ROLE: James Bond in Dr. No

WHO LET IT GET AWAY: Cary Grant. Despite being Bond producer Albert Broccoli’s best man, Grant said “I don’t” to the offer, and Sean Connery got the role instead. Of course, many studio executives objected to the decision, and even Bond creator Ian Fleming said Connery “wasn’t exactly what I had in mind.”
REGRETTABILITY METER: Low. By the 1960s, Cary Grant already had a spectacular film career. If he’d accepted the role (as Broccoli later revealed), it would’ve been just a one-movie deal.

THE ROLE: Neo in The Matrix

WHO LET IT GET AWAY: Will Smith turned it down to star in the forgettable action flick Wild Wild West, and the part went to Keanu Reeves.
REGRETTABILITY METER: Low. In an interview with Wired, Smith said, “I would have absolutely messed up The Matrix. At that point I wasn’t smart enough as an actor to let the movie be—whereas Keanu was.”

THE ROLE: Vincent Vega in Pulp Fiction

WHO LET IT GET AWAY: Michael Madsen, who was stuck in lengthy rehearsals for Wyatt Earp. John Travolta got the role instead and, almost overnight,
transformed from a Hollywood has-been into one of the most bankable stars in the business.
REGRETTABILITY METER: High. Madsen called Wyatt Earp “a big waste of time.”

THE ROLE: Gandalf in the Lord of the Rings trilogy

WHO LET IT GET AWAY: Sean Connery, who’d never read the J.R.R. Tolkien series and claimed he “didn’t understand the script.” (Can you say karma?)
REGRETTABILITY METER: High. In return for playing the role, New Line Cinema offered the Scottish actor up to 15 percent of worldwide box office receipts, which would have earned Connery more than any actor had ever been paid for a single role—as much as $400 million.

THE ROLES: Sundance in Butch Cassidy and the Sundance Kid, Jimmy “Popeye” Doyle in The French Connection, and Captain Benjamin Willard in Apocalypse Now.

WHO LET THEM GET AWAY: Steve McQueen.

REGRETTABILITY METER: Tragically high. McQueen turned down the role of Sundance simply because costar Paul Newman refused to give him top billing. Later, McQueen declined the lead in The French Connection because he felt the part was too similar to the tough cop he’d played in 1968’s Bullitt. Gene Hackman took the part and won an Oscar for it. And finally, in 1978, McQueen told Apocalypse Now director Francis Ford Coppola to shove off when he was offered the lead. McQueen’s non-negotiable asking price was $3 million; plus, he didn’t feel like spending four months shooting in the Philippine jungle. Instead, Martin Sheen landed the role, and despite suffering a heart attack during the stressful production, he gave one of cinema’s greatest performances.

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