All careers, even the great ones, have their ups and downs. Michael Jordan had his Wizards run. Shaq spent a year with the Celtics. Tiger Woods has his entire life right now. Our legends are fallible, but they don’t become legends without the sort of dizzying heights of success we mere mortals can only dream about. A great man once said that life is a highway, and if you really are gonna ride it all night long, you might get a flat tire or two in the process.

For Will Smith — one of the last great pop culture icons of the 20th century — those career highlights and lowlights have been dramatic. His new film, Focus, might finally be a return to form after a succession of very public embarrassments, so in honor of this possible comeback, we asked the intrepid Grantland staff to pinpoint the exact moment when we were blessed with Peak Will Smith … and the sad day when Big Willie Style crashed his Hollywood spaceship into the show business valley.

Peak — Ali

Bill Simmons: When I wrote my Ali review for ESPN.com in 2001, I started it with the courtroom scene in which Will Smith — for about 45 seconds — actually became Muhammad Ali. The problem with that movie, and the problem with Will Smith for these past 25 years in general, is that Will Smith has always played Will Smith. He didn’t have a choice. Will Smith was its own character. Will Smith was an A-lister. Will Smith made a shitload of money. Everyone liked Will Smith. Why play anyone else?

When he jumped from music to TV, he played the Fresh Prince … but that was really Will Smith. In Six Degrees of Separation, he played Gay Street Hustler Will Smith. In Bad Boys and Independence Day and Men in Black and six or seven other popcorn movies that came and went and made hundreds of millions of dollars, he played Action Hero Will Smith. In Enemy of the State, he played On-the-Run Will Smith. In The Pursuit of Happyness, he played Homeless Dad Will Smith. In Hitch, he played Rom-Com Will Smith. In After Earth, he played I’m Becoming a Fucking Weirdo Will Smith. You never forgot he was Will Smith. Not for 25 years. He didn’t want to take chances. He didn’t want to risk the empire he was building. He didn’t want to turn anyone against him. That was the premise behind my 2011 column about him, when I tried to figure out why he was Hollywood’s safest bet. The answer? He played it safe. Always.

Even Ali was something of a safe bet — get yourself in crazy shape, play a beloved American hero, learn how to box, adopt Ali’s semi-drawl, give a bunch of interviews saying you just made your most meaningful film, and celebrate your certain Oscar nomination. We’ve seen that script before. It’s a flawed movie that’s too long and tries to do too many things, and whenever I stumble across it on cable, I always get excited for about four minutes before remembering that it drives me crazy. And usually, that’s when I change the channel … unless I am anywhere near that courtroom scene. I stick around for that one. It’s the best scene of Smith’s career. He explodes out of the courtroom with real purpose, the music swelling, the anger building, his words spilling out of his mouth like lyrics. They keep thinkin’ they gonna break me, but they are not gonna break me. For less than a minute of a well-played, well-executed, and exceedingly lucrative career, Will Smith allowed himself to become someone else. It never happened again.

Valley — Seven Pounds

Mark Lisanti: The hopeful narrative right now is that Will Smith is back. Or at least backish, because a world where Big Willie Style is once again on top of his game is a more interesting one than one in which he’s sitting in the hull of a wrecked spaceship, remotely helping his real-life son avoid four-legged phallus-beasts that can smell fear.¹

Seven Pounds, Smith’s speedy reunion with The Pursuit of Happyness director Gabriele Muccino, was perhaps an even bigger debacle than After Earth. A refresher — this is going to be full of spoilers, but if you’re afraid this will ruin your subsequent enjoyment of the movie, we humbly request that you throw your Netflix password down the nearest well and then email us photographic proof you’ve done so — for the uninitiated: Will Smith plays a man who kills seven people, including his fiancée, in a BlackBerry-induced car crash. He then impersonates his IRS agent brother to investigate seven “good people” who could receive the gift of his organs, releasing him from the crippling guilt of taking those seven souls. “But he’s alive!” you say. “How are they going to get his organs?” you ask.

Maybe you’re the curious sort who already watched the above video. If not, therein lies your answer. He’s going to fill up a bathtub with ice, call 911, and then release a poisonous box jellyfish into the water, which will sting him — painfully! — to death. This is perhaps the only suicide by jellyfish in cinematic history. It is something to behold. You should never watch any scene from Seven Pounds but this one.

Welcome backish, Mr. Smith. Even Medium Willie Style is welcome here.

Peak — Bad Boys

Chris Ryan: Peak Will Smith is 1995-97 Will Smith. Bad Boys, Independence Day, Men in Black. I’ve seen two things take off like that in my lifetime: space shuttles and mid-’80s Tom Cruise. Within Peak Will Smith, there is Peak-Peak Will Smith. It’s Bad Boys. And within Bad Boys, there’s a peak Will Smith moment.²

A couple of years back, Fennessey did an oral history of Michael Bay for GQ. The whole Bad Boys section is great, but the part that jumps out is the discussion of Will Smith, running with his button-up shirt flapping open. According to producer Jennifer Klein, women at a test screening in Lakewood, California, were screaming with delight, such was the body heat coming off the Fresh Prince.

It’s an iconic shot, sure — a testament to Bay as a master propagandist. Smith acknowledges the role it played in making him a Movie Star: “There was a transformation from the cute guy next door who could make you laugh to a guy who might be able to handle himself in a bar fight and a bedroom.” He’s right and he’s wrong. I knew Smith was going to become a movie star after Bad Boys, but it had nothing to do with him running shirtless.

There’s a moment early on in Bad Boys when Smith and Martin Lawrence go to see a contractor they think could be useful to their case. When they get to his house, the guy is dead, which is something Smith doesn’t like. It’s supposed to play as a comic moment for Lawrence — dry-heaving, tiptoeing, recoiling at the corpse. Instead, it becomes the moment Will Smith becomes Paul Fucking Newman. Cool as you like, totally in control, and funny — all the more so because of Lawrence hamming it up. Only a couple of guys can play a scene like that — Cruise, Harrison Ford, Mel Gibson. Right there, in a pedestrian, connective-tissue scene, Smith is a movie star. And he didn’t need a single frame of slow motion to prove it.

Valley — Wild Wild West

Dave Schilling: You guys screwed me again. When we came up with this idea, all I wanted to do was write a 500-word defense of “Will 2k,” the one song that was able to get our species through the looming cataclysm of the Y2K bug. All I asked was that I got to explain how Will Smith simultaneously wrote the most dated holiday-themed song of all time and the most timeless holiday-themed song like some kind of goddamn pop-musical wizard. I was so excited about getting down on bended knee and proposing to “Will 2k” in front of God, my family, and the Internet.

But I can’t. I just can’t bring myself to allow this publication to post an article about Will Smith’s greatest failures without anyone mentioning perhaps the most embarrassing moment in black history other than the series premiere of Homeboys in Outer Space. Wild Wild West is a sin, a pox on all of our houses, and the first movie to reveal that Will Smith was actually human and not a genetically engineered Universal Soldier designed to sell movie tickets.

SGranitz/WireImage The Fresh Prince and the Black Mamba, in happier times

Wild Wild West is a comedy that’s not funny. It’s an action movie that’s not exciting. It’s a Western with a robot spider. It’s all the more galling because this is the true end of Peak Will Smith. From Bad Boys to Independence Day to Men in Black to Enemy of the State, Will Smith was on an unprecedented roll that may never be repeated. He was an ebony god whose only mission was to entertain the entire planet through any means necessary. Big Willie Style, his 1997 solo album, sold 6 million copies in the United States alone. So what was our man’s next move? Slap-fighting with Kevin Kline for two hours. Have any two actors been less successful in the buddy-cop genre?³

As bad as this shit-stain of a movie is, it’s not rock bottom. Oh, no. It gets worse. You see, Will Smith — being a consummate professional — did everything he could to make Wild Wild West a mega-blockbuster in 1999. Where some movie stars might balk when it comes time to ride a horse out into the audience at the MTV Movie Awards and bark your way through an overwrought performance of your novelty single while fireworks and Dru Hill explode in the background, Will Smith said, “Can I wear a dumb hat, too?”

I am convinced that Wild Wild West was a Will Smith heat check gone horribly wrong. I truly believe he did this film thinking, How many embarrassing situations can I put myself in while looking cool? That heat check ended right here.

Peak — The Fresh Prince of Bel-Air

Rembert Browne: The Fresh Prince of Bel-Air is a great show — classic, even — one that holds up better than most products from the 1990s. But much like its still-in-syndication, always-watchable-if-on-and-it’s-always-on cousin, Seinfeld, it’s easy to forget about some of the side characters who come in and out of the show, because the main cast is so strong.

A thing about Seinfeld that is hard to ignore is the girlfriends of Jerry Seinfeld — many of whom went on to become (or were already on the way to becoming) household names. Looking back at it now, you’re like, Damn, Jerry. You really pulled that off. And I’m not convinced you deserved it. You bastard.

From Courteney Cox to Christine Taylor to Teri Hatcher to Kristin Davis, Jerry was on a tear. It’s impressive. But it’s still not as impressive as what Will Smith lucked into on The Fresh Prince.

Over almost six years, Willard Smith flirted with, kissed, tried to holler at, dated, was seduced by, or was stood up at the altar by Victoria Rowell, Vivica A. Fox, Jasmine Guy, Tisha Campbell, Lela Rochon, Garcelle Beauvais, Queen Latifah, Tyra Banks, Kim Fields, Stacey Dash, Pam Grier, Elise Neal, Robin Givens, and Nia Long.

Typing that was like watching Waiting to Exhale on the WB and then Soul Food on UPN.

Goofy-ass Will Smith did that. This might not be Peak Will Smith for the public, but when you look back and think, I wonder when Will was least worthy of his great life? it’s got to be the early ’90s, largely in part to this laundry list of queens.

What a greedy dude.

The only person missing from this list is Jada Pinkett. AND THEN HE MARRIED JADA PINKETT THE FOLLOWING YEAR.

Valley — After Earth

Holly Anderson: Earlier this month, Will Smith, out loud and on the record, referred to After Earth as “the most painful failure in my career,” and first, it’s his career, let him decide; second, this is the guy who made Seven Pounds, so we have to assume he knows what he’s talking about. That should be the end of the discussion, but let’s not let this moment pass without pointing out that I can live through all of the following in a given film:

• A character named CYPHER RAIGE (all caps for emphasis, but he might actually spell it that way, you never know; why go around with the name CYPHER. RAIGE. without embracing it con gusto?)
• A planet named Nova Prime not dedicated to an all-encompassing museum devoted to the life and work of Glenn Close
• A protagonist getting plucked from danger by a giant-ass bird, worst-part-of–The Hobbit–style …
• TWICE

But to sit through all that and not once get to hear Will Smith utter, “Welcome to After Earth”? How DARE you, sir. I’m not even asking him to say it through the fourth wall while winking. This is not an unreasonable request.

Alex Pappademas: What Holly said. But also: There is no better metaphor for Will Smith’s oddly thwarted leading-manhood than this movie, most of which he spends incapacitated and bleeding out in the wreckage of his spaceship/career while leading his uncharismatic son through a monster-filled forest/thinly allegorized version of Scientology’s “auditing” process. Crippling or otherwise de-physicalizing black leading men to help white audiences relax around them is a rich Hollywood tradition; recall that the one time the similarly explosively charismatic Denzel Washington starred opposite Angelina Jolie in a movie, he played a tetraplegic.

But After Earth was Smith’s own idea. He gets a story credit, he got M. Night Shyamalan a work release from movie jail in order to entrust its direction to someone too grateful to question that story’s logic, and he cast his own dumb kid in the thing. He is the master of his own unmaking, which would almost be impressive as an act of movie-star persona-negation if he’d contrived anything remotely compelling to replace it with. Instead he delivers tough-love koans about fear in a solemn and vaguely Sam the Eagle–ish monotone. This is rock bottom.

Peak — Independence Day

Amos Barshad: Usually, when engaging with formerly great artists caught in the doldrums of their career, I try to rationalize: They gave us so much! How much more can we ask for??? That’s true with Will, of course. From 1990 (the first season of Fresh Prince) to, I would say, 2007-08 (I Am Legend, Hancock) he was a prodigious one-man entertainment machine. Isn’t it enough?! Well, um — no!

Because just look at him. He looks incredible. He’s clearly still got the chops. And he should be giving us more. Listen — Tom Cruise, at age 52, just gave us Edge of goddamn Tomorrow. And there’s just no particular reason Will can’t still churn ’em out like Tom.⁴

But we didn’t come here to grumble. We came here to praise. To that end: ID4 is a perfect blockbuster, and not only because of Will. To be fair, its single best part is The Speech.

https://www.youtube.com/watch?v=oj16vfbsM9A

The second single best part? WELCOME 2 EARTH.

Quick thought exercise, though. Switch Captain Steven Hiller and President Whitmore, and guess what: Will — although being way too young for the White House — still crushes that role, and that speech, while Billy Pullman is left a laughingstock.

In conclusion: Will Smith is a precious resource that we should tap until the barrel is bone-dry.

Valley — I Am Legend

John Lopez: Once upon a time, in a movie world long since lost to the mists of financial crisis, there ruled one undisputed king of the box office. This stately Lord of the Stars could open any film of any genre — science fiction, romantic comedy, inspirational dramedy — to hundreds of millions of dollars. All you needed on your one-sheet were nine magical letters: Will Smith. Nothing makes me feel older than remembering when Will Smith could do no wrong. Of course, we now know even this mega-matinee demigod would face his own Götterdämmerung. And for me, the moment just before the Fall, when Icarus reached his greatest heights even as his wings were melting from the overpowering rays of his own ego, is obvious: I Am Legend.

The title alone should say it. To be clear, I Am Legend is not a good movie: the shoddy CGI zombies wheezing like your German shepherd after a vigorous round of butt sniffing at the dog park look only more atrocious eight years on.⁵ But damn if that film didn’t make $585 million worldwide. In the moment, we even acted like it was kind of maybe good, and there is only one person responsible for that reaction: Will Smith.

With his charisma firing on full nitrous boosters, he sold everyone on a movie that consists pretty much of him tooling around New York, talking to his dog, and shooting mannequins. Sure, there are flashbacks and Alice Braga shows up to motivate the final explosions. But really, the movie is built on us watching Will Smith talk to himself — in a quasi-creepy way that, come to think of it, contains some eerie foreshadowings of his subsequent career. But we bought it — hook, line, and stinker: Will Smith, the literal savior of humanity. Don’t deny it; you cried when his dog died.

Peak — “Gettin’ Jiggy Wit It”

Steven Hyden: This song was released as a single in January 1998, and two months later it was the no. 1 song in the country. But somehow that doesn’t convey how extraordinarily popular “Gettin’ Jiggy Wit It” was. I feel like it was the no. 1 song for three years.

My memory of “Gettin’ Jiggy Wit It” is that it was on the radio at least 73 times per hour. I swear DJs would pause in the middle of “Gettin’ Jiggy Wit It” in order to play “Gettin’ Jiggy Wit It,” and then play the rest of “Gettin’ Jiggy Wit It.” Radio stations repeatedly played “Gettin’ Jiggy Wit It” sincerely in 1998 like radio stations repeatedly played Nelly’s “Hot in Herre” ironically in 2014. This was sort of unexpected: Will Smith was a movie star in 1998 — the biggest movie star in the world, really. His three most recent films were Bad Boys, Independence Day, and Men in Black. Later on in ’98, he was in Enemy of the State. Will Smith was king, no longer a Fresh Prince. But now Smith was back making music and doing that more successfully than ever, too. He crossed over from rap to film and then parlayed that into an enormous pop career. “Gettin’ Jiggy Wit It” demonstrated that late-’90s Will Smith could do anything he wanted. He took a high and made it higher. And since Wild Wild West was still a year away, he had some time to enjoy the view.

1. An utterly unbelievable turn for socially engineered thought leader Jaden Smith, who fears nothing but the disabling of the shift button for his tweets.

2. This is not the same as a favorite Will Smith moment. My favorite Will Smith moment was, is, and forever will be “Who the fuck is Reggie!?”

3. A case can be made for Pat Morita and Jay Leno in Collision Course, but I’ll save that for my first book!

4. This is a sticking point with the audience and Eddie Murphy, too: He looks great. Can’t he just still be great, then?

5. To say nothing of that last-minute rewrite of the ending of a reboot whose very raison d’etre was to go back to Richard Matheson’s classic novel.