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Will Smith's 6 Best And 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: A lot of critical bombs

Will Smith proved his acting skills — with both comedy and drama  — back on "The Fresh Prince of Bel-Air" and hasn't stopped since. He's been nominated for a multitude of awards and just picked up an Oscar for "King Richard." The guy knows his craft. Nevertheless, he's not always the best judge of what roles he should take and which he should maybe pass on. Just check out the guy's Rotten Tomatoes page. There are plenty of freshly reviewed movies on the list (although a lot of those only list him as a producer), but few truly great films that most would consider classics. "Independence Day," "Men In Black," "Hitch," and "The Pursuit of Happyness" are popular movies, for good reason. But few would call any of them "masterpieces" on the same level as what some of Smith's peers were doing at the same time.

And, of course, there's no shortage of absolute stinkers. Most infamously, Smith has been in 1999's wildly unfunny "Wild Wild West" (16%), 2012's embarrassingly bad M. Night Shyamalan sci-fi dump "After Earth" (12%), 2016's infamous super-flop "Suicide Squad" (26%), and Netflix's orc-cop dramedy "Bright" (27%), which tried to be cool and funny and fell well short of both.

Smith's remarkable talent makes his mediocre filmography even more frustrating.

BEST: The Fresh Prince gets his acting start

It's hardly a single "moment," but "The Fresh Prince of Bel-Air" was such a success that we felt it warranted a mention here. Think about it: The show has all the ingredients you need for a timeless, endlessly rewatchable classic. It managed to be edgy enough without boring teen viewers or offending parents. It had a uniquely fun but not restrictively wacky premise — a working-class Philadelphia teen is sent to live with his bougie extended family in California after getting in a fight. As for the tune that's definitely in your head right now, it just might be the greatest theme song of all time. It has great characters, room for drama and warmth in between all the laughs, sharp writing that often doesn't get enough credit, and of course, early '90s Will Smith himself.

Smith, then known mainly for being one-half of Grammy-winning hip-hop duo DJ Jazzy Jeff and the Fresh Prince (guess which one he is), was an absolute knockout on the NBC TV show. By the time the final season wrapped in 1996, The Guardian says that Smith's superstardom had elevated him well past where TV stars — and Black actors — often found themselves: bona fide blockbuster leading man status.

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: 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: 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: 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 brings in the money

You may have noticed that Will Smith isn't in too 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 critical badge of honor. But that doesn't mean the actor isn't bankable, as we can see by looking at his films in descending order of box office gross (via The Numbers).

Only one of Smith's movies has broken the once unbreachable $1 billion mark (that would be 2019's "Aladdin," in which he plays the Genie). But several movies have come close, including 1996's "Independence Day" ($817 million), the aforementioned "Suicide Squad" (which, despite its reception, managed to pull in a respectable $746 million), 2008's "Hancock" at $624 million, and 2012's "Men In Black 3," which clocks in at $654 million. Add in several others in the low- to mid-hundreds-of-millions range, and you're looking at a current, cumulative box office haul that stretches enviably into the billions.

Smith is now considered one of Hollywood's most desirable leading men, capable of anchoring everything from romcoms like "Hitch" to horror-thrillers like "I Am Legend" to acclaimed dramas like "King Richard," for which he just won an Oscar.

WORST: Slapping Chris Rock at the 2022 Oscars

Oscars co-host Chris Rock was on a roll, as evidenced by this uncensored footage. He turns his sights on Jada Pinkett Smith and says, in reference to her shaved head (she suffers from Alopecia, as per NBC News), "Jada, I love ya. 'G.I. Jane 2,' can't wait to see it!" She rolls her eyes, prompting Rock to say, "That was a nice one!" Apparently, not everyone agreed. As has been pointed out ad nauseam, Jada's husband, Will Smith, laughs along with everyone else when the joke is first made. But the next time we see him, seconds later, he's storming the stage Kanye style.

"Uh oh!" Rock says as the audience laughs, right before Smith infamously open-hand smacks him across the face in front of millions of viewers. Only when Smith returns to his seat and hurls obscenities at a visibly shaken Rock — demanding he "keep my wife's name out your f***ing mouth!" — does the audience realize that what they just saw was indeed not staged at all. The incident immediately overshadowed the rest of the night and became one of the most talked-about moments in award season history.

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: The slap fallout was brutal for Smith

Although the slapping incident did generate discussion about alopecia and a debate over whether or not Chris Rock's joke went too far (per the Guardian), most of the coverage was focused on the "Slap Heard 'Round the World." Regular folks and celebrities alike condemned the incident and Will Smith's subsequent Oscar win. Comedians rallied around Rock and expressed worry that Smith had normalized violence against comics from offended audience members. In an interview with Gayle King, Jim Carrey said he was "sickened by the standing ovation" the embattled actor received after his tearful acceptance speech and lamented that Smith's behavior stole the spotlight from everyone else at the event who worked hard to earn their place there.

Smith did release an apology on Instagram, saying, "My behavior at last night's Academy Awards was unacceptable and inexcusable. ... I would like to publicly apologize to you, Chris. I was out of line and I was wrong." But even if his apology was sincere, consequences were inevitable. The day after the Awards, the Academy of Motion Pictures Arts and Sciences announced that it was investigating the incident, per Entertainment Weekly. In anticipation of harsh penalties, CNN says Smith voluntarily resigned from the organization, saying he "will accept any further consequences the Board deems appropriate."

But the fallout continued, with Netflix and Apple TV+ pulling out of a bidding war for a Will Smith biopic that no longer seems likely to hit streaming services anytime soon.