The Evolution of Will Smith

Image via Complex Original

Year: 1988

Ranking on the Billboard Charts: This smash reached No. 12

What Will's Doing: Introducing us to his career-long charismatic corniness. Young Will bops about like a hybrid of Kel Mitchell and Chance the Rapper. In this breakout video, he protests his mother's schoolwear selection of a "plaid shirt with a butterfly collar" and "double-knit reversible slacks." In tacit retaliation, he borrows his mom's new Porsche and picks up a woman he dubs "toots." She makes some upper-thigh advances that distract him from the cop who books him for hitting 90 without a license. Iconic.

Year: 1990

Ranking on the Billboard Charts: N/A

Ranking in Our Hearts: No. 1

What Will's Doing: Participating in a superstar rap group for Earth Day. After Quincy Jones raps geriatrically about toxic waste, Will enters flanked by a squad of mainstream '90s rappers: Tone Loc, Queen Latifah, Ice T, Kid 'n Play, and Heavy D. This stacked, well-intentioned crew proceeds to drop bar after bar about the proper way to dispose of chemicals, the negative effects of air pollution, and the poisonous state of our oceans. Young Will Smith pulled these Jedi mind tricks where he did something super goofy, yet made you think he was actually doing the coolest thing anyone’s ever done. 

Year: 1990-1996

Cultural Impact: Fresh Prince still re-runs its six seasons on television to this day.

What Will's Doing: Cementing his inevitable superstardom. Will basically plays himself, transplanted from Philly to Beverly Hills where he rocks the loudest patterns ever on cable television, drops an unbeatable array of pick-up lines, and navigates the intricacies of young adulthood with a large surplus of likability. But despite its frenetic comedy, the show’s lasting power lies in its deep emotional core—exemplified by the titanic, semi-improvised "How come he don’t want me, man" scene.

Year: 1995

How Much Money He's Making: $2 million

What Will's Doing: Establishing himself as a go-to blockbuster star. In Michael Bay’s directorial debut, Will teams up with Martin Lawrence as best buddy narcotic cops that must track down those who jacked $100 million dollars of heroin from the evidence locker—the duo’s biggest bust. Over and over, bad guys point guns at them, but they distract with yaps before executing nasty counters. Will sprints with an unbuttoned shirt, cracks rare rough language jokes and thousand-yard stares during swirling close-ups. The flick grossed seven times more than its budget and confirmed that Will was way too big of a star to be confined to television.

Year: 1996

How Much Money He's Making: $5 million

What Will's Doing: Making you super-proud to be human. Will plays a NASA-aspiring fighter pilot who outmaneuvers an alien in the Grand Canyon. Then he punches it in the face, says "Welcome to Earth" while he lights a cigar—which, just wow. He joins a ragtag resistance against the planetary invaders led by Bill Pullman’s President who delivers a speech from the back of a pick-up truck that gets us so motherfucking jacked to be from Earth. Smith crushes his role as a badass who is tender to his wife (Vivica A. Fox) and their super-adorable, sassy son (Ross Bagley). He helped save Earth for the first time and imbued this gargantuan popcorn-flick with humor and depth—both things he’d do a lot going forward.

Year: 1997

How Much Money He's Making: $5 million

What Will's Doing: Kicking alien ass in another big-time blockbuster. Will pairs with Tommy Lee Jones in the classic cop cliche of a hip young dude who falls under the wing of a grizzled old guy, but this time the criminals come from other solar systems. Smith proves his savvy by chasing down a super-agile alien, dragging a loud-ass table and capping a cardboard 8 year-old white girl with a quantum physics book during a range-shooting test. Smith's comedy compliments Tommy Lee Jones’ unflappable gruffness and they square off with a humongous space roach in Will's second Earth-saving.

Year: 1998

How Much Money He's Making: $14 million

What Will's Doing: Holding his own next to Oscar-caliber actors Jon Voight and Gene Hackman. Will tones down the goofy flails and plays it straight as a humble labor lawyer that gets unwillingly roped into a shady government imbroglio. This unravels after he receives an incriminating tape of an NSA agent whacking a congressman who won’t approve an incredibly invasive surveillance bill. (Unfortunately, years later, the P.A.T.R.I.O.T. Act—a bill identical to what the villains wanted in the film—still passed.)

Year: 1998

Ranking on the Billboard Charts: No. 1—for three weeks straight

What Will's Doing: Simultaneously jumping the shark musically and demonstrating his unparalleled star power. In this massively popular music video, Will wears a silver velvet sport coat, a jet-puffed Adidas sweatsuit, a pharaoh's headdress, and a tropical forest two-piece get-up—all looks only he could rock, or would even think about rocking. Will Smith is a wardrobe hero. Over an irresistible funk beat, he spits some family-friendly lines and crafts an infinitely catchy hook. But this song has aged like Brendan Fraser and is objectively not good. Still Will’s tip-top charisma carried it as he introduced the world to a little shimmy-hop dance move that he executes at a luau, the Statue of Liberty and a disco-ball-laden house of mirrors.

Year: 1999

How Much Money He's Making: $7 million

What Will's Doing: Set in the Reconstruction era, Smith plays the flatly stoic companion to Kevin Kline’s doofiness as the two of them seek to bring down a Confederate war criminal and a mad steampunk scientist and an 80-foot hydraulic Tarantula. Smith sings a song about his character for the closing credits. The ditty won a Razzie, but also led to the most absurd live performance of all time wherein a maroon-suited Smith rides in on a stallion, receives a mid-song assist from Kool Moe D and Dru Hill, then raises Stevie Wonder through the floor who brings it home with a sparkling piano riff. Even the man’s failures are spectacular.

Year: 2000

How Much Money He's Making: $10 million

What Will's Doing: Doing his best with a racially cliche role. Smith works a smooth subtlety into his Southern koans about focus that sooth Damon’s swing tics and personal demons. Still, the gorgeously shot, but thematically shallow picture deploys Smith’s charisma solely as a prop to propel Damon to sporting success and romantic revitalization with his lost love—an at-her-peak Charlize Theron.

Year: 2001

How Much Money He's Making: $20 million

What Will's Doing: Catching his first Oscar nomination. Smith snuggles into the skin of Muhammed Ali and captures the legend's charisma, lyrical cadence and unchecked self-confidence. He beefed up for the role and forwent "Hollywood fighting" for the real deal—actually boxing with real-life, championship-caliber fighters. Outside the ring, he protests the US government wanting him to shoot Viet Cong. The role (somehow) wasn’t a commercial smash, and quibbles can be made with execution, but it reestablished Smith as a pinnacle star.

Year: 2002

How Much Money He's Making: $20 million plus 10 percent gross

What Will's Doing: Cutting the period pic crap and giving the people what they want. Set five years after the first, J needs to unwipe K’s memory and convince him he’s a secret agent and not the boss of a Post Office that employs beat-boxing aliens. Smith whoops a two-headed Johnny Knoxville, roasts David Cross' dweebishness, and laser-blasts the regenerating noggin of Tony Shalhoub who plays an extraterrestrial pawn shop owner with a wonky eye and a stash of bulbous non-Earth guns. In this slightly repetitive plot, Smith’s delirious confidence again distracts and defeats the bad aliens to restore order to the universe. He saves the world for the third time and reestablishes himself as show business' summer-flick champ.

Year: 2003

How Much Money He's Making: $74.6 million

What Will's Doing: Making a shameless money grab. Like all of Michael Bay’s recent efforts, this sequel sucked, but made a barge full of cash. The much puffier Smith-Lawrence duo are still narcotics cops, but instead of heroin, it's ecstasy. This time they’re up against the KKK, the Russians and the Cubans—an unlikely trifecta of evil if there ever was one. Smith and Lawrence exchange passionless banter between fights, car crashes, and gargantuan explosions. The mindlessly entertaining action flick rode Smith’s still-cresting popularity to $270 million in gross profits.

Year: 2004

How Much Money He's Making: $28 million

What Will's Doing: Shifting from aliens to robots. Smith plays a wary, semi-bionic, leather-duster-clad detective. He investigates a docile-faced servant robot, Sonny, that achieves sentience and is no longer super psyched about his people’s programmed slavery. Eventually, after some dope fights, Will and Sonny bond, then team together to bring down the central hive brain that determines human beings must be saved by a forceful robot takeover—as artificially intelligent super-computers are known to do. The film features some poignant meditations on what being alive really means. And Smith carries the flick with weary persistence and salty wit as he defends Earth from non-human hordes for the fourth time.

Year: 2004

How Much Money He's Making: $15 million

What Will's Doing: Making one for the kids. Smith voices Oscar, a cleaner fish that exploits his proximity to a shark-killing accident to take credit for the peak predator’s death. Now the "Shark Slayer," Oscar vaults to immediate fame and prestige, which flings him headlong into phoniness. In what could have been just a paycheck-snatch, Smith traces a surprisingly long character arc for a kid’s flick as he loses the audience, then wins them back with a comforting, if a bit hokey, soliloquy about accepting people for who they are.

Year: 2005

Ranking on the Billboard Charts: No. 7

What Will's Doing: He’s rocking layered wife-beaters, red forearm bands and a personalized, auto-mechanic jumpsuit. To be fair, Smith flows effortlessly over a stomp-clap beat, but comes off very "Old Man Yells at Cloud" when he complains about scantily-dressed women and fans downloading music rather than frequenting record stores. He proved he could still spit and purged the last remnants of his musical ambitions on Lost and Found. But nobody really cared.

Year: 2005

How Much Money He's Making: $20 million

What Will's Doing: Will Smith plays a teacher of goobers who want to slay and somehow humanizes the character using all of his considerable charms. Midway through, Hitch scolds a sweaty Kevin James for his flamboyantly bad dance moves like the "Q-Tip" and the "Pizza Maker." And it's the most hypocritical moment of his career. Big Willy literally made his name doing goofy-ass sashays. The flick contains crackling chemistry with Eva Mendes and one solid tip: the 90-10 rule, which in theory is smooth as hell, but in practice, we can personally testify is not foolproof.

Year: 2006

How Much Money He's Making: $71.4 million

What Will's Doing: Getting his second Oscar nomination by making audiences blubber as he chases the American Dream. Before Jaden ran out of fucks, he starred with Dad in this beyond-heartwarming, true story about a homeless man who flips solving a Rubik's cube into an unpaid internship into a well-paying stockbroker job. Smith digs deep and just crushes every scene—whether he’s telling Jaden, “Don’t ever let someone tell you, you can’t do something—even me;” or pretending that dinosaurs are chasing them to distract from the fact that they have to sleep in a BART bathroom; or communicating a lifetime’s worth of joy with nothing more than a couple nods, a few lip quivers and lightly reddening eyes that can’t blink lest they start pouring.

Year: 2007

How Much Money He's Making: $25 million

What Will's Doing: Holding down Manhattan by himself with his dog. When a cure to cancer accidentally turns most people into pale nocturnal zombies (whoops!), Will shacks up in a fortified brownstone, hunts for deer in Times Square and runs relentless experiments for a cure. He delivers this generation’s Old Yeller moment when he chokes out his soon-to-be-zombified pooch while whispering the lyrics to "Three Little Birds." The mutants compromise his pad just as he discovers the vaccine. And so, to save the planet for the fifth time, Will sacrifices himself so the mother and son he met can take the vial of salvation for wide distribution. The blockbuster proved Will doesn’t need supporting actors to gross a quarter billi.

Year: 2008

How Much Money He's Making: $20 million, plus 20% gross

What Will's Doing: Teasing America with a sweet-ass beginning, then blowing it in the second half. He starts out as a sauced Superman who stops a train with his shoulder, hucks a beached whale into a sailboat and impales an Escalade full of robbers onto a radio tower. But his slapdash heroics result in billions of collateral damage, so the always-charming Jason Bateman offers to do pro-bono publicity. But then, this meta-fun flick takes a baffling turn. Apparently, Hancock is an immortal whose demi-god power is linked to his proximity to his soulmate Charlize Theron, who happens to hiding out as Bateman’s wife.

Year: 2008

How Much Money He's Making: Unknown. (That it was such a flow kept it under wraps.)

What Will's Doing: This weird drama takes place after Will sends a mid-drive text and causes a crash that kills six strangers and his fiancee. Understandably grief-stricken, he seeks to atone. Not understandably, he decides to do this by donating organs to seven people that he deems worthy before committing suicide via a box jellyfish’s excruciating sting. Smith’s odd, ambiguous performance is exemplified when he mocks Woody Harrelson, a blind meat-selling telemarketer, for not being able to see, then calls him a virgin. Will succeeded in doing what everyone thought he couldn’t: playing an unrelatable, unlikable character

Year: 2012

How Much Money He's Making: $20 million

What Will's Doing: Winning us back by kicking alien ass. In this, there’s an intergalactic supervillain named Boris the Animal who breaks out of a moon prison, rips a hole in space-time and kills K in the past—opening up an alternate present where Earth is vulnerable to an invasion by his generally unpleasant species. Will travels through time, meets Josh Brolin doing a splittingly accurate young Tommy Lee Jones and the duo collaborate for Will’s sixth saving of the planet. At the end, J learns that Boris killed his father, and that K watched over him until the day he was ready for the black suit. The way Will thanks K is so cheeky and subtle and wonderful. He wraps this billion-dollar trilogy with indie-movie emotional deftness—and that’s why no matter what he does, he’s a national treasure.

Year: 2013

How Much Money He's Making: $20 million

What Will's Doing: Will conceived the story, then convinced M. Night Shyamalan to co-write, direct and cast his son in the lead role. Essentially, Will and Jaden must survive on Earth, 1000 years in the future, where everything has evolved specifically to kill humans by sensing their fear. So Will teaches Jalen to conquer fear. But on a hostile planet filled with tailored predators, fear is about the only emotion you can play. So Jalen’s performance got panned—sparking his far-more-interesting pivot to gender-fluid fashion and social media performance art. But Jaden’s not all to blame. The effects are SyFy-channel bogus, the script is littered with plot holes and the general story arc is filled with nods towards the freaky cult religion that Will has dabbled in. Not his best, but that's on its way.

Year: 2015

How Much Money He's Making: $5 million

What Will's Doing: Conning folks with Margot Robbie. This sleight-of-hand flick looks pretty, but doesn’t develop much in the way of a story or moral. Luckily, Will and Margot are exceptional at being charming and good-looking. So plopping them in gorgeous locales and giving them snappy, sexy lines makes up for the shallowness. They dupe rich dudes and fall in and out of love. Whatever, the plot isn’t important. What matters is, somehow, at the age of 46, Will can still rock a crisp cut, work his belly into a six-pack and seem more believable as Robbie’s love interest than the dad-bodish, five-years-younger Leo DiCaprio.

Year: 2015

How Much Money He's Making: $10 million

What Will's Doing: Following up fluff with unrewarded Oscar bait. He stars as real-life Nigerian doctor, Bennet Omalu, who spotted CTE in the bashed brains of former NFL players. Smith adopts the doctor’s African brogue, nuanced humility and intense outrage at the multi-billion-dollar corporation that obscured facts and valued profits over human beings. Despite his fine performance, the picture bears the smudges of NFL-sanctioned softening and adheres to a too-conventional structure for it to really shine. Still, Smith banked some "maybe this guy deserves an Oscar" cred.

Year: 2016

How Much Money He's Making: $20 million

What Will's Doing: Playing the world’s greatest marksman, Deadshot. After Tom Hardy dropped out as a result of The Revenant’s repeated filming fiascos, Smith joins Jared Leto and Margot Robbie in an anti-hero flick for the ages. His character’s backstory is as dark as any; while trying to protect his idolized older brother from their abusive father, he misfires the family rifle and kills the wrong guy. This trauma spurs him to improve his aim and fills him with an utter disregard for human life, including his own. The superhero blockbuster is familiar territory, but he’ll be in a novel role as the biggest star within a crowded ensemble. We can't wait.