Will Smith Almost Took The Red Pill (And 9 Other Roles He Just Missed Out On)

Will Smith has four Grammy awards, guys. Four! The guy who had middle-aged dads in 1997 embarrassing their kids by singing “Gettin’ Jiggy With It” also was Hollywood’s biggest cash cow between 1996 and 2007. Will Smith had eight consecutive films open at the number one at the box office, each grossing over $100 million. Even with After Earth tanking — because people don’t want to look at Jaden Smith for two hours — Forbes still listed him as the most bankable star in the world in 2013.

Even Hollywood kings from west Philadelphia have their fair share of box office victories slip past them though, and Will Smith is no different. With the Fresh Prince turning 46 today, here’s a look back at ten roles he missed out on while building his Willennium empire.

Snake Eyes (1998) — At one time Will Smith was attached to the film. Paramount felt that Smith — who had just come off the mega success of Men in Black and was attached to Wild Wild West — was asking too much and dropped him for Gary Sinise.

The Matrix (1999) — As revealed in our Matrix Facts You Might Not Know piece, Will Smith was originally supposed swallow the red pill. The offer was on the table at the same time as Wild Wild West and Smith decided that he’d rather wear a cowboy hat than put on another pair of cool-looking black sunglasses.

Osmosis Jones (2001) — I’ve never seen Osmosis Jones, and considering that the movie’s box office grab was only $14 million out of a $70 million budget, it seems like a lot of other people didn’t either. The movie had an incredibly strong cast of Bill Murray, Laurence Fishburne, David Hyde Pierce, and at one time had Will Smith in the lead role. Smith was interested in the part, but reportedly couldn’t fit the movie into his schedule and Chris Rock took the role.

Phone Booth (2002) — Smith was attached to the part that would eventually go to Colin Farrell before the script even had a director attached. It was never meant to be and Smith dropped the part to focus on Ali.

The Truth About Charlie (2002) — Just like Phone Booth, Smith’s dedication to the Muhammad Ali biopic — along with his MIB contract — prevented him from taking nearly any role in 2001. Smith was in talks to play the Cary Grant part in the Truth About Charlie remake, but scheduling wouldn’t permit and the part was given to Mark Wahlberg.

Hotel Rwanda (2004) — Smith was suggested for the part that would nab Don Cheadle an Oscar nomination, but the studio opted to save the cash it would cost for Will Smith and pour the money back into the film. That extra cash went into hiring 950 extras a day to better show the scale of the events that would unfold in the drama.

Man on Fire (2004) — Several actors that had previously worked with Tony Scott were offered the lead part of Creasy, but of course it was Denzel Washington who would seal the deal. Robert De Niro, Tom Cruise, Bruce Willis, and Smith all had their names tossed in the hat.

Charlie and the Chocolate Factory (2005) — Tim Burton was always committed to casting his bestie, Johnny Depp, in the role of insane chocolate maker Willy Wonka, but Warner Brothers pleaded with him to look at other actors. Warner Brothers suggested that Tim Burton think about Will Smith as well as Michael Keaton and Nicholas Cage for the part, but in the end, not even the mighty studio execs were able to breakup Burton and Depp.

Mr. & Mrs. Smith (2007) — C’mon, Will Smith, Mr. and Mrs. Smith, it just makes sense that he should have been in this movie. Brad Pitt was always director Doug Liman’s top choice for the part, but Brad Pitt was having doubts about taking the role when Gwynenth Paltrow was in talks to play Mrs. Smith. When Pitt showed uncertainty Liman looked at Johnny Depp and Will Smith as possible replacements. Depp was exhausted from doing those pirate movies and Smith already attached to I Am Legend. In the end, Gwynenth Paltrow was bounced and Angelina Jolie was free to enter and reel Pitt in to help her rescue third-world orphans.

A Star is Born (Probably Never) — At one time this musical remake had Will Smith and Whitney Houston attached. The project has been shuffled around for years, and its most recent pairing had Beyonce joining Smith on the project — that was in 2011 though, before she got pregnant and Blue Ivy brought the project to a halt.

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