While the Wachowskis were picking actors for The Matrix towards the end of the last century, they famously approached Will Smith to play the character Neo. At the time, the actor was riding high with some big productions under his belt in the few preceding years.

Between 1995 and 1998, Smith had starred in Bad Boys, Independence Day and Men in Black, all of which had gone on to become smash hits. Comparatively, the Wachowskis were still relative unknowns in Hollywood.

They also approached Smith with the script which he didn’t quite understand, and the actor turned them down. He instead chose to star in the steampunk Western film Wild Wild West, which turned out to be a complete critical and commercial failure.

Keanu Reeves would go on to play Neo, as the character and film soon became absolute modern classics. Smith would later admit that this sequence of events added up to the biggest regret of his otherwise stellar career.

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Neo is not the only role that Will Smith turned down, however. And while not all the movies he refused went on to great success, there is one other that he might regret just as much as The Matrix.

Will Smith Also Said No To A Role In Django Unchained

Will Smith was directed by Barry Sonnenfeld for Men in Black, although the filmmaker had not been the first choice for the job. Columbia Pictures and Amblin Entertainment had two prior names who they considered to helm the project, but were turned down on both occasions.

One of the directors who said no to the project was Quentin Tarantino, on the back of his first two movies: Reservoir Dogs and Pulp Fiction. The talented screenwriter would then go on to make a number of other major hits, including Kill Bill 1 & 2 and Inglorious Basterds.

In April 2011, he finished writing the script for his next project, a revisionist Western titled Django Unchained. For the titular role, he had a couple of actors in mind, including Michael K. Williams and Will Smith.

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Smith reportedly said yes to the part when originally asked, but then later changed his mind and turned it down. Django Unchained made $425 million at the box office, and won two Academy Awards, out of five nominations.

Why Did Will Smith Refuse To Feature In Django Unchained?

Will Smith spoke at length about the episode that led to him saying no to Django Unchained in January 2016. He had joined his fellow actors Mark Ruffalo, Michael Caine, Benicio Del Toro, Joel Edgerton and Samuel L. Jackson for an Actors Roundtable for The Hollywood Reporter.

In the discussion, Smith delved into his reasoning for saying no to Quentin Tarantino. He explained how he felt that the two of them saw the character Django in significantly different ways.

“I had said yes to Django, but it was more about the creative direction of the story,” said Smith. “To me, it's as perfect a story as you could ever want. A guy that learns how to kill to retrieve his wife that has been taken as a slave.”

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“When I choose movies, I'm choosing the arc,” he continued. “I read the first 35 pages and I read the ending… [The] idea is perfect. It was just that Quentin and I couldn't see [eye to eye]. I wanted to make the greatest love story that African Americans had ever seen from American cinema.”

Will Smith Also Did Not Agree With The Violence In Django Unchained

Will Smith supposedly had an in-person meeting with Quentin Tarantino over the possibility of him playing Django. At the end of the day, they apparently could not reach a consensus; the actor said he wanted to tell a story of love, but all he could see in the script was endless violence.

“[Quentin and I] met. We talked. We sat for hours and hours and hours about it. I wanted to make that movie so badly, but with that story I felt the only way I could make that movie is it had to be a love story, not a vengeance story,” Smith said at the THR Roundtable.

“When I'm looking at [the script], it's like, ‘No, no, no. It has to be for love,” he added. “Violence begets violence. For me, I just couldn't connect to violence being the answer. Love had to be the answer.”

Smith didn’t speak as ruefully about Django as he did regarding The Matrix. The irony, however, is that he has been in the news this year for publicly meting out violence on Chris Rock at the Oscars.