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Will Smith’s 10 Will Smith-iest Moments of All Time

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What is a definitive Will Smith moment? It’s hard to say, since Will Smith himself has been so loathe to give them to us, despite the fact that he hasn’t really been out of the spotlight since …1987? When he and DJ Jazzy Jeff opened for Run DMC?

Those early years when he was only known as The Fresh Prince (if you knew him at all) were not particularly notable because Will is not a particularly notable emcee, but he made his mark by being uniquely palatable. You liked him even if you didn’t love what he was doing, and this has been the secret to Will Smith’s success ever since.

Even at his peak, Will Smith is the Patron Saint of the Pretty Good. His movies don’t win Oscars, but you’ll catch them on television. His singles weren’t bangers, but nobody minded when they came on the radio back in 1997. Even The Fresh Prince of Bel-Air was never a ratings giant, but held up solidly over the course of six seasons, eventually garnering an influence that far outweighed its initial popularity. It was a pretty good show.

And through all this, Smith has emerged more or less unscathed, buoyed by one of Hollywood’s most irresistible personalities. He’s been a smartass action hero, a charming tradesman of one-liners and a scenery chewing Oscar hopeful, but never all at once and rarely to the point where you feel he’s operating at Peak Will Smith, which is why it’s so hard to find definitive Will Smith moments. When his performance was its best, the movie didn’t deserve him (Ali). When the movie was good enough to deserve him, he seemed out of place in it (Pursuit of Happyness). Even this week’s Suicide Squad, which has a capable understanding of how to set Smith up for success, fails in almost every other sense.

So strange as it might be to say for a man whose career is now stretching into its third decade, you can’t help but feel like Will Smith hasn’t peaked yet. To that end, here’s the Gradient team’s assessment of Will Smith’s most definitive moments so far, with the caveat that we pray Will Smith hasn’t had his actual definitive moment yet.

10. Miami

“Just the Two of Us” was a bigger hit and “Gettin Jiggy Wit It” is more fondly remembered, but Smith’s never had a non-movie promotional music video that captures his essence like “Miami” does. For one, you’ve got his swagger on full display, brushing off adoring women the second he emerges from his private jet (one of those women is Eva Mendes. Not the only time she’ll appear on this list!) For another thing, you’ve got the line where he actually says “every nation: Spanish, Haitian, Indian, Jamaican, black, white, Cuban and Asian.” I could not love that line more. You could spend your life trying to find a better line written in 1997, and you’d die a failure.

But what makes this a truly definitive Will Smith moment is when Will and the boys drive a speedboat to an island that magically remixes “Miami,” dropping the Whispers’ “And the Beat Goes On” sample for a Caribbean flavor. It is wild and ostentatious and awesome, and it shows just how deftly Smith can sell an idea that might have looked terrible on paper, but feels way more interesting once you find out he’s the one who does it. That’s sort of the song in a nutshell, as Smith tries hard here to convince America that Miami is better than NYC, Chicago, LA and Philadelphia, and that is just objectively false. But coming from Smith, you almost buy it!

9. “I take it to the max every day!”

Bad Boys‘ legacy rests neither on Will Smith or even Martin Lawrence so much as it rests on this: being the world’s introduction to sentient guitar solo Michael Bay. It’s not the worst introduction in the world, as it’s not Bay’s worst movie, but every cliche that would come to define Bay’s oeuvre is here in teeth-grinding form. Bad Boys is an unbridled celebration of juvenile testosterone that already feels like nobody on set quite knows how to tell Michael Bay “no.”

So how does Will Smith’s definitive Will Smith-iness fit into all this? The script was originally written as a vehicle for Dana Carvey and Jon Lovitz (can you imagine?!?) before being retooled for Martin Lawrence and Arsenio Hall. But legend has it that Bay caught an episode of The Fresh Prince and decided Smith was right for the role instead.

Never let it be said that Bay doesn’t have an eye for casting. Who besides Smith could deliver the line “I take it to the max every day!” without dissolving into fits of giggles? Who looks better in a pair of sunglasses? Edgar Wright’s Hot Fuzz would lovingly mine Bad Boys for laughs in 2007, but the movie is already its own parody and only Smith seems to understand it, delivering even the most headache inducing lines with a wry gravity that would solidify his presence as a major movie star.

8. “I’m a consultant.”

If Smith’s turn in Bad Boys was proof he was a born action star, Hitch would be proof (his only proof, to date) of his rom-com chops, which are — of course — pretty good. Once again, Hitch is only a so-so movie even by rom-com standards, but the performances invigorate a clumsy script and Smith gives his considerable all. Hitch also deserves credit for being the exceedingly, distressingly rare film of any genre to feature two leads of color. In a sane world, the movie’s success would have led to more such pairings but, well, that’s not the world we live in.

Of course, the dance instruction scene is the most famous Hitch moment, but that’s more a definitive Kevin James moment than it is a definitive Will Smith moment. This meet-cute with Sara Melas (Eva Mendes! Again!) really brings all of Smith’s charm to bear and showcases his particular talent for nonverbals. His exasperated eyes when Mendes gets hit on by a revolting Lothario. His skeptical nostril flair (yes, that’s a thing, and Smith uses it a lot) when Mendes suggests he’s handling this interaction pretty well. Smith’s bag of acting tricks isn’t bottomless, but it’s effective, and he employs them to winsome affect throughout Hitch. 

7. Oh my god, do not watch this.

Okay, this clip is from Will Smith’s 2007 starring vehicle I Am Legend, and it features an Old Yeller moment in which he has to put his own dog down after it gets infected by a zombie-like virus and oh my god, do not watch it, I beg of you. If you’re having a good day, it’ll ruin it. If you’re having a bad day, it will make it exponentially worse. Skip this clip, go home and hug your dog. In I Am Legend, Smith is New York City’s last living person, and his only friend is this dog and then he has to strangle his dog to keep it from turning into a zombie and, ugh, no. No. This clip is rated “N” for “Nobody” because nobody should watch this, and that goes for you.

6. Turning down the role of Neo in The Matrix to play what’s-his-name in Enemy of the State.
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This isn’t the only famous role Smith has turned down. It’s not even the only role rejection story on this list. But this is The Matrix, for crying out loud. It’s very fun to imagine Smith’s spin on Neo, jawing his way through the whole red pill/blue pill debate and adding a little bit of glint and irony to the whole “I know kung-fu” bit. It’s also fun to know Smith went with Enemy of the State instead, a movie best known for playing on USA every damn day.

If anything, Keanu Reeves seems better suited for Enemy of the State, a fine but forgettable (if eerily prescient) government surveillance thriller. And while it’d be easy to write off Smith’s rejection of The Matrix as a mistake, it’s important to keep two things in mind. First, The Matrix is a trilogy, only a third of which is watchable. Second, for as big as The Matrix is, it also ended up being a graveyard for just about everyone involved. Nobody’s out there making Sad Will Smith memes.

5. “That boy even dream he whup me he better wake up and apologize.”

Some things just can’t be filmed and Muhammad Ali’s million-watt life is one of them. No conceivable movie could have captured it in all its glory. You probably can’t do justice to Ali with a performance either but by God, Smith comes close. His riff on the famed Joe Frazier speech here is enough to get the little hairs on your neck floating like butterflies, as Smith lends his cocky bravado to one of the few egos in the world who outsized his own. It’s a good look, and it was Smith’s first major motion picture proof that he’d be around for a while.

4. “Just the Two of Us”

Smith’s most famous progeny, Jaden and Willow, have become famous for their kush-fueled dorm room neo-woke philosophizing and absolutely fire fashion swerves. But the first Smith Jr. to reach mega star status was Trey, from Smith’s first marriage to Sheree Zampino. “Just the Two of Us” was our first glimpse at the Will Smith that was to come: the indomitable family man who would leverage every last ounce of his personal fame to get his kids in the spotlight. As the box office receipts and critical shade for After Earth will go to show, this has not always gone well. But it went over fantastic on “Just the Two of Us”, which had its eye on the future in more ways than one. See pregnant Jada Pinkett Smith in the video? Jaden was upstaging Trey before he was even out of the womb.

3. Turning down Django Unchained because Django wasn’t in it enough.

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Okay, this story is way better than Smith turning down the lead role in The Matrix because, well, just listen to this incredible quote from The Guardian:

“Django wasn’t the lead, so it was like, I need to be the lead,” Smith told Entertainment Weekly while promoting his new science fiction film After Earth. “The other character was the lead! I was like, ‘No, Quentin, please, I need to kill the bad guy!'”

To recap, Will Smith turned down the role of Django in Quentin Tarantino’s Django Unchained because he felt like Django, the man whose name is the title of the damn movie, wasn’t enough of the lead. The only way this could be a more definitive Will Smith moment is if there was a hip-hop single to commemorate it. Hey, speaking of!

2. “Men in Black”

What is the best part of this video? The part where the alien starts singing? Smith’s disappearing card trick? “Just bounce with me”? No, the best part of the video is imagining Smith trying to talk the legendarily curmudgeonly Tommy Lee Jones into mugging into the camera for his sadly brief intro. Perhaps no two stars have ever been more mismatched than Smith — who never met a public relations machine he couldn’t fuel on his smile alone — and Jones, who never met a public relations machine he gave a frick about. That lent some real world tension to their cliched buddy cop dynamic on Men In Black and made that movie’s most indelible cultural footprint, the music video, all the more intriguing. Can you imagine the day of the music video shoot rolling around and Smith on the phone with Tommy Lee Jones, begging him to get out of bed, promising they’d wrap it up in one take? If we had that audio, it’d be at the top of this list.

1. “Welcome to earth.”

Was there any doubt? Was there any doubt that this would be number one? Numero uno? It’s all here. If you haven’t watched it in a while, I cannot recommend it highly enough, because it’s even better than you remember. It’s significantly better than Bill Pullman’s speech, which is probably Independence Day‘s most well-known moment. “Ship all banged up!” Smith shouts, before tearing open the hatch on an alien space ship and punching a hostile extraterrestrial right in its jellyfish head. Oh, and the cigar! Don’t forget the cigar! It’s incredible.

You know who won the Oscar for best male actor in 1996? Nicolas Cage for Leaving Las fricking Vegas. Give me a break. I would put this two minute scene starring Will Smith up against the entirety of Cage’s filmography. It’s not just the Will Smith-iest moment of all time. It’s one of the great moments of the ’90s, which puts it on the shortlist for the greatest moments of all time. It’s definitely the highlight of my own personal life.

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