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Since the 1990s, few movie stars can claim the success rate and widespread popularity of Will Smith. In the span of a decade, he went from one-half of the popular hip hop duo DJ Jazzy Jeff & The Fresh Prince to star of a hit TV show and then finally to the top of the box office charts. In fact, Smith once held a record that proved just how hard he worked to achieve so much. But in the midst of that success, he revealed the movie that ultimately crushed him.

Will Smith holds his hands in front of him as he speaks at a microphone
Will Smith | Chung Sung-Jun

Will Smith starred in hits ‘Independence Day’ and ‘Men in Black’

Before TV’s The Fresh Prince of Bel-Air, Smith had never acted before. That NBC series — which ran for six seasons from 1990 to 1996 — gave the star some much-needed on-the-job training. And during its run, he began to test himself as a movie star. It was during this period that Smith appeared in Where the Day Takes You, Made in America, Six Degrees of Separation, and Bad Boys. But once his TV show ended, that’s when his film career exploded.

Just months after The Fresh Prince of Bel-Air wrapped, Smith starred in 1996’s Independence Day. That film and the following year’s Men in Black gave Smith back-to-back hits, both of which were released on the Fourth of July weekend. Even 1998’s Enemy of the State — an R-rated political thriller co-starring Gene Hackman — became a blockbuster hit. According to Box Office Mojo, the film earned $251 million against a $90 million production budget.

The actor’s streak of blockbusters ended with this 1999 film

Given that hit streak, reteaming with Men in Black director Barry Sonnenfeld for Wild Wild West seemed like an easy win. Like their previous collaboration, the film — based on the 1960s TV series — was a buddy cop-style sci-fi action-comedy featuring a theme song performed by Smith. Alas, Wild Wild West didn’t go as planned. Although the movie opened strong, it was maligned by critics and fans alike, a revelation that hurt Smith, he told Empire.

“My biggest emotional defeat and the greatest emotional pain I’ve had as an actor was when Wild Wild West opened up to $52 million. The movie wasn’t good. And it hurt so bad to be the number one movie, to open at $52 million, and to know the movie wasn’t good.”

Smith has historically committed wholeheartedly to everything he’s worked on. So it stands to reason that the realization his latest project doesn’t measure up must have been hard. Still, Smith didn’t apparently hold Sonnenfeld accountable for how Wild Wild West turned out. The actor and director would go on to team up on two more Men in Black movies, released in 2002 and 2012.

Will Smith has taken on a broader range of movies ever since

In the years since Wild Wild West, Smith has made a more concerted effort to diversify his films roles. In fact, just two years later, he starred as boxing legend Muhammad Ali in director Michael Mann’s Ali. That film earned the actor his first Academy Award nomination and proved he could do a whole lot more than quip and fight CGI monsters.

Today, Smith alternates between blockbusters and more grounded dramatic stories with ease. His most recent film, King Richard, earned the actor his first Academy Award for playing Richard Williams, father to tennis pros Venus and Serena Williams. Prior to that, he reteamed with Martin Lawrence for 2020’s biggest hit, Bad Boys for Life.

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