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Will Smith's 6 Best And 6 Worst Career Moments

Ah, Will Smith. The actor started off rapping with DJ Jazzy Jeff & the Fresh Prince, then got his acting breakthrough on "The Fresh Prince of Bel-Air," then leaped to Hollywood leading man status, then got some Grammys, starred in Oscar-nominated hits and commercial flops alike, got weird with his family, and punched Chris Rock. It's been quite a ride.

Will has worked hard to curate an image of himself and his family that's warm, inviting, fun, hugely talented, and lovable. But it hasn't been smooth sailing, and it seems like every career triumph is offset by an awkward moment, critical flop, or scandal. How well this all balances out is, in the end, up to each individual who's either in love with "Hitch" or "Independence Day" or exasperated by all the Smith family shenanigans. Not sure where you stand?  We're here to help with this list of the highest peaks and lowest valleys of the Fresh Prince's career. 

BEST: Smith becomes the first musician to win a Grammy for rap

Although it often gets overshadowed by his success as an actor, Will Smith's rap career was a big factor in his '90s stardom. But "Gettin' Jiggy Wit It" wasn't the first song he became famous for — he was a hip-hop veteran by that point. According to Britannica, he and his bandmate Jeffrey Townes — who toured together as DJ Jazzy Jeff and the Fresh Prince — got their first Grammy for 1988's "Parents Just Don't Understand." In fact, it was the first Grammy ever awarded for rap music.

But it wouldn't be Smith's last. Pop Sugar says he's won four Grammys out of an impressive total of eight nominations. After "Parents Just Don't Understand," DJ Jazzy Jeff and the Fresh Prince picked up another trophy for 1991's "Summertime." Then came his solo music career and "Men In Black." No, not the movie — the song he wrote for the movie, which got him his third Grammy win. Then in 1998, 10 years after his first triumph at those awards, he got his fourth and final win for his signature song from that era, "Gettin' Jiggy Wit It."

He's had some nominations since then — no small feat — but has since put his music career on the shelf while he focuses on acting. For most people, four Grammy wins and eight nominations would be enough to retire. For Smith, it was a side project.

WORST: Will stars in After Earth

A brief glance at Will's Rotten Tomatoes page proves he's no stranger to critical bombs. His most popular movies include "Independence Day" (67% on the critics score), "Men In Black" (92%), and dramatic biopics like 2001's "Ali" (68%) and 2021's "King Richard" (90%). Pretty good –- but few masterpieces on the order of what some of his peers were doing at the same time.

And of course, the same list includes Will's stinkers, too. Between "Wild Wild West"(16%), "Bright," (27%), and "Suicide Squad" (26%), these movies are arguably more notable for being bad than his biggest hits are for being good, if that makes sense.

But hoo boy, it's hard to beat M. Night Shyamalan's 2013 sci-fi flop "After Earth," when it comes to regrettable projects, which received a rancid 12% on the Tomatometer. In this movie, Smith plays a wounded father to a scared kid (played by Will's actual son, Jaden), where they crash land on a hostile planet. It's hard to determine whether the acting, direction, or screenplay was the worst part of this embarrassing dump of a film. But for Will, it was almost certainly how hard the cynical backlash was on his son Jaden, just 14 at the time, after all the work they'd put in together as father and son. As he told Esquire, "That was a valuable lesson for me a few years ago with 'After Earth.' That was the most painful moment in my career."

BEST: Nominated for Ali

Will Smith showed his dramatic chops in the '90s, most notably in a "Fresh Prince of Bel Air" scene in which the fictionalized version of himself lets out what is clearly serious pain at being abandoned by his father and collapses into Uncle Phil's arms. But by and large, Smith was considered an action star with a background in comedy. He still had work to do to prove he could handle more serious roles.

He got his chance by starring in 2001's "Ali," a biographical sports drama about legendary boxer Muhammad Ali, formerly known as Cassius Clay. The movie, which follows Ali's career from the mid-'60s to the mid-'70s — when he won several iconic matches and controversially commented on ongoing issues like the Vietnam War and the Civil Rights Movement — didn't exactly break box office records. But it was a hit with critics, with the Rotten Tomatoes critics consensus saying: "Though perhaps no film could fully do justice to the fascinating life and personality of Muhammad Ali, Mann's direction and Smith's performance combine to pack a solid punch."

Notably, the role also nabbed Smith his first-ever Oscar nomination for best actor in a leading role. It was proof that while he was certainly bankable as an action/comedy star, he could hold his own with the best when it came to drama.

WORST: Smith turns down The Matrix in favor of Wild Wild West

Will Smith was riding pretty high at the end of the '90s. "The Fresh Prince of Bel Air," success in music, and leading man status in several blockbusters had all turned him into a household name. But he was almost the star of another tail-end-of-the-'90s franchise: "The Matrix." The only problem? He wanted to star in "Wild Wild West" instead. It's no secret that while the former is a beloved and thought-provoking sci-fi classic, the latter was a bomb and a stain on the filmographies of everyone involved.

Will posted a video to his YouTube channel explaining why he turned down the role of Neo, which of course went to Keanu Reeves instead. According to him, he was a bit overconfident at the time following the success of "Independence Day" and probably trusted his gut a little too much. At one point, he was even about to pass on "Men In Black." Luckily, calmer heads prevailed.

"I made 'Wild Wild West,'" Smith said. "I'm not proud of it." However, he goes on to claim, "Keanu was perfect. Laurence Fishburne was perfect. So I probably would have messed 'The Matrix' up. I would have ruined it, so I did y'all a favor."

In his defense, it is pretty weird to think about charismatic Smith in a role that Keanu famously played as woodenly (is that a word?) as possible. Oh, what could've been.

BEST: Will and Jaden star in The Pursuit of Happyness

Nobody's arguing that Willow and Jaden Smith would've gotten anywhere without Willpower (seriously, be born rich to famous parents, folks — it works wonders). But as annoying as Will constantly pushing his kids in the world's face might be, nobody can deny it's a win for the Fresh Prince whenever his kids make headlines or get a fat paycheck. And it's not like they don't deserve it at all: NME notes that Willow's 2010 song "Whip My Hair" was a top 10 hit in the US (even if the resulting industry pressure nearly turned her off from that line of work for good, according to the article), while Jaden had both a hit song with Justin Bieber and starred in the critically praised "The Karate Kid" reboot that same year. Pretty impressive stuff for the Smiths.

And Will clearly enjoyed including his kids in projects whenever he could. He starred with Jaden in a number of movies, and while "After Earth" was a wince-inducing mistake, "The Pursuit of Happyness" certainly wasn't. In this 2009 movie, Smith stars as a homeless man desperately trying to make a better life for his son Christopher (Jaden Smith). Critics were fans, according to Rotten Tomatoes, and it was an excellent debut movie for Jaden, who was just 8 at the time. Will is an excellent actor, but his portrayal of a man who deeply loves and wants the best for his son was clearly genuine.

WORST: The Smiths get way, way too open with their personal lives

If the constant marketing isn't enough proof, the Smiths seem to think the world is clamoring for every tiny detail of their personal lives. But while the continued existence of checkout aisle tabloid rags proves there's still a market for that content, there's a fine line between "open and honest" and really, really awkward.

As News 18 points out, Smith goes into excruciating detail in his memoir "Will" about how he had so much sex when he was young that he "developed a psychosomatic reaction" to it that made him sick. Later in the book, he talks about his sex life with Jada Pinkett Smith: "We drank every day, and had sex multiple times every day, for four straight months ... as far as I was concerned, there were only two possibilities: (1) I was going to satisfy this woman sexually, or (2) I was going to die trying." Imagine being one of his kids and reading that.

Speaking of Jada and the kids, where do we even begin with "Red Table Talk"? E Online has some receipts on the show, where we learned that Willow learned about sex after catching her parents in the act and that, um ... self-service has always been a part of Jada's life. Listen, transparency is cool and all, but so is keeping some things to yourself. Especially when your kids are right there. Do we really need to hear this stuff?

BEST: His kids find success

Roll your eyes at Will Smith constantly pushing his kids down the world's throat all you want. It's very forced, and nobody here is making the argument that either Jaden or Willow would've found any success if they didn't have Will freaking Smith as their dad (be born rich, folks, it works wonders). But running on Willpower (get it?) doesn't mean the kids aren't talented or don't deserve success. And their success is a win for Will, so it lands on the "best" half of this list.

Other than being a Smith, Willow is most famous for her 2010 single "Whip My Hair." It's undeniably catchy and was unavoidable for months — a level of success that even Will Smith couldn't pay someone to fake. NME says the song, which peaked at No. 5 on the U.S. pop charts, was such a hit that it actually drove her away from the music industry entirely. So while she didn't end up being a pop star, you can't say it's because she failed.

As for her brother Jaden, he also launched a music career when he was featured on Justin Bieber's 2010 song "Never Say Never," which peaked at No. 8 on the Billboard Hot 100 and was used as the theme song for the movie he starred in, "The Karate Kid" reboot with Jackie Chan (which, by the way, isn't bad). And while "After Earth" was a bomb, "The Pursuit of Happyness," another movie he co-starred in with his dad, definitely wasn't.

WORST: His kids' success came at a cost

It's nice growing up rich, to famous and well-connected parents. But you have to wonder what kind of long-term damage gets done when you live in the limelight and reach adulthood without having to weather the challenges of life that force normal people to mature.

Not even the Smiths were immune to the pain of fame. In fact, they never shied away from it at all, since Will so publicly tried to turn his kids into a brand. It took a heavy toll. Buzzfeed has the details on a conversation he had with daughter Willow, who was touring Europe with Justin Bieber, off the back of her 2010 smash-hit, "Whip My Hair."

"Thank you, Daddy, I'm finished," Willow, then only 10 years old, said to her dad after leaving the stage. When he tried to tell her she had to finish the tour, she said, "It doesn't matter to you that I'm done, Daddy?"

That line broke Will, who gradually realized his feelings had never been considered when he was growing up, and that he'd dropped similar baggage on his daughter. Fortunately, the encounter changed his approach to parenting, from what he says was "pushing and prodding and cajoling people into the vision that I had, demanding that people do the things I had envisioned for them," to realizing his job was to "water and nourish and nurture that seed to become what it already is."

BEST: Will made $100 million for Men In Black 3

You might've realized that Will Smith isn't in many billion-dollar blockbusters. Those seem to be reserved for superhero movies these days, and Smith's main attempt to get his foot in that door resulted in "Suicide Squad" — hardly a badge of honor. But that doesn't mean he isn't bankable, as we can see by looking at his films in descending order of box office gross (The Numbers). Add it all up and you realize that although only one of his movies (2019's "Aladdin") made it to the $1 billion mark, his cumulative box office haul stretches into the billions.

And of course, that means Will himself isn't cheap. Business Insider brought the receipts on 16 of the highest paid movie roles of all time. The movies listed might surprise you (who would've thought that after all his hits, Jim Carrey's biggest payday would've been for "Yes Man"), but the actors featured probably won't.

Will Smith himself appears no fewer than 3 times on the list, more than anyone else who didn't make the cut based on a single deal (like Adam Sandler's multi-movie deal with Netflix) or a series (Keanu Reeves in "The Matrix" original trilogy). It's true. He pulled in $35 million for the upcoming sequel to "Bright," and $40 million for "King Richard." Most impressively, though, he nabs the top spot on the list with an ridiculous $100 million paycheck for his role as Agent J in "Men In Black III."

WORST: Finding out his wife cheated ... on TV

"Red Table Talk" is a show in which Jada Pinkett Smith, daughter Willow Smith, and mother Adrienne Banfield-Norris say a whole bunch of things that the general public really doesn't need to know. But the most noteworthy incident by far has to be the July 2020 episode in which Jada had Will on the show so she could openly admit to the father of her two children that rumors she had cheated on him with rapper August Alsina in the past were indeed true.

"And it all started with him just needing some help, me wanting to help his health, his mental state," she said, according to Daily Mail. "As time went on, I got into a different type of entanglement with August." She goes on to explain that she and Will had been going through a rough patch. "I just wanted to feel good. It had been so long since I felt good ... and it was really just a joy to just help heal somebody."

Even if you didn't watch the bombshell episode, you almost certainly ran across memes of Will Smith's face from the episode, where it looks like he's bursting at the emotional seams. Even more emasculating and embarrassing, the article points out that while Will has referred to the incident as a "transgression" that he's willing to look past as a loyal husband, Jada has since claimed she didn't see the affair as a "transgression" at all.

BEST: Smith wins the Oscar for best actor

It's weird to even mention in the context of the now infamous "slap" that preceded it by a few minutes, but we do need to note that Will Smith did take away one of the top prizes at the 2022 Academy Awards: best actor. And it's not like he didn't earn it: The decision to give him the prize was obviously made before he assaulted Chris Rock, and the reasoning was sound — Smith received massive acclaim for his portrayal of Richard Williams, the hard-driving father of tennis superstars Venus and Serena Williams.

On Rotten Tomatoes, Smith is called out by name for his performance in the critics consensus: "'King Richard' transcends sports biopic formulas with refreshingly nuanced storytelling — and a towering performance from Will Smith in the title role." Don't believe us? Just watch the "cops in the house" scene and tell us he didn't have an award coming his way.

But again, the slap overshadowed what should've been a triumphant moment. "I want to apologize to the Academy," he said in his tearful acceptance speech (via BBC). "I want to apologize to all my fellow nominees. ... Art imitates life. I look like the crazy father, just like they said about Richard Williams. But love will make you do crazy things."

He did get a standing ovation when he was done, but the blowback was only beginning.

WORST: Will slaps Chris Rock at the Oscars

The 2022 Oscars should've been a triumphant moment for Will, but his Best Actor victory was overshadowed by what occurred just moments before. In response to a joke host Chris Rock made at Jada Pinkett's expense (which touched on her Alopecia), Will stormed the stage Kanye-style and slapped Rock across the face, in front of millions. Any notion the incident was staged was put to bed when Smith shouted obscenities at Rock after returning to his seat. It immediately became one of the most talked about moments in award season history.

The fallout of the Slap Heard 'Round The World hit immediately after the ceremony. In an interview with Gayle King, Jim Carrey said he was "sickened by the standing ovation" Smith received after his Oscar win. Meanwhile, the internet was ablaze with outrage, and comedians rallied around Rock, expressing concerns that Smith had just normalized violence against comics from audience members.

Smith did speak on Instagram the next day, saying, "I would like to publicly apologize to you, Chris. I was out of line and I was wrong." But as sincere as the apology may have been, consequences were inevitable: the BBC says that in April, the Academy of Motion Picture Arts and Sciences elected to ban Smith for 10 years over the incident, while The New York Post says Netflix and Apple pulled out of a bidding war for an upcoming Will Smith biopic.