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From “Parents Just Don’t Understand” to his current standing as an A-list star, Will Smith has always seemed unstoppable. The actor has achieved success in just about every facet of the entertainment industry. Much of that, however, is due to his work ethic. In fact, at the height of his fame, Smith stepped outside his comfort zone to protect his movie career.

Matt Damon in a black suit and silver tie poses with Will Smith in a grey suit and hat at the premiere of 'The Legend of Bagger Vance'
Matt Damon in a black suit and silver tie poses with Will Smith in a grey suit and hat at the premiere of ‘The Legend of Bagger Vance’ | David LEFRANC/Gamma-Rapho via Getty Images

Will Smith starred in several 1990s hit, but something was missing

It’s wild to think Smith’s starring run on NBC’s The Fresh Prince of Bel-Air ended less than two months before Independence Day. The actor couldn’t have hoped for a smoother transition from television to the big screen. Bad Boys, Independence Day, and Men in Black established his on-screen persona. But the failure of Wild Wild West proved Smith wasn’t infallible.

That 1999 movie reunited Smith with Men in Black director Barry Sonnenfeld. Clearly, the plan was to replicate their earlier hit. Yet, Wild Wild West proved that Smith’s undeniable charisma alone wouldn’t automatically translate into box office success. The actor maintained his superstar status afterward by proving he was willing to take a chance.

The actor considers ‘The Legend of Bagger Vance’ a major turning point

The next year, Smith starred opposite Matt Damon and Charlize Theron in The Legend of Bagger Vance. In the film, Smith plays a mysterious caddy who arrives to help Damon’s golfer get his game — and his life — in order. Around the time of its release, Smith explained to The Morning Call why he signed up for the movie in the first place.

“I ran into Steven Spielberg at a party, and I jokingly asked him why he never hired me for his movies. Steven said, ‘Oh, you’re too big for my movies.’ I laughed it off. … But it clicked in my mind. The persona I created had become too big for the stories I want to tell. I had started to overshadow the characters I play. People see me on screen and go, ‘Oh, look, it’s Will Smith.’ …

I thought Bagger Vance was a great opportunity for me to just turn it off. This is the first time in my career that I completely surrendered all my instincts and my natural desire to bend scenes into the Will Smith thing. … It was a really scary place to be in. It’s frightening to feel in a scene that this persona you’ve created is trying to crawl out, dying for you to do something or say something that is funny, something that will shake up a scene and say, ‘Hey, notice me!’’”

In the end, The Legend of Bagger Vance didn’t really do what Smith hoped. The film was a box office dud and received middling reviews. But it was the actor’s first time stretching for a movie since his first big role in 1993’s Six Degrees of Separation.

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Will Smith went on to deliver much more range in future movie roles

From The Legend of Bagger Vance on, Smith began striking a much more even balance of blockbuster hits and riskier projects. This approach didn’t always pay off, but he did land two Oscar nominations. In both Ali and The Pursuit of Happyness, he successfully shed his typical on-screen persona.

At the same time, Smith tapped into what audiences love about him with movies such as Hitch, Suicide Squad, and sequels to Bad Boys and Men in Black. And the actor might still win an Academy Award too. In King Richard, Smith will play the father of tennis pros Venus and Serena Williams. The film is due for release in fall 2021, in the heart of awards season.

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