Considering Will Smith’s impish charisma and still-boyish good looks, it’s shocking to realize he’s been around for nearly 30 years. Take that Paul Rudd. Audiences have literally witnessed the actor grow from a 24-year old MC of the hip-hop duo DJ Jazzy Jeff & The Fresh Prince to family man. He’s garnered chart toppers and box office hits; television stardom; and blissfully lived as the other half of a power couple with wife Jada Pinkett-Smith. He’s one of the few movie stars left, a cultural crossover sensation capable of leading a film to profitability based on his sheer talent and aura.
This week, the actor returns with Bad Boys for Life, the third installment in a series that began in 1995. It’s a fitting reoccurrence as the first entry marked the beginning of the performer as a box office staple. In fact, Smith’s career can be split into three arcs. His first decade covered the “young hotshot” archetype in which he portrayed bachelors maturing over the course of a film. He then transitioned to “weathered adults,” family men who have lived through hardships. And, more recently, he’s taken on a scattershot of roles, from science fiction to biopics, as villains or mentors.
The films below make up an assemblage of those personas. Even so, his charm and comic timing is present in every role, be it action stars to men at the end of their ropes. Altogether, we feel these make up the best performances of his career.
On the surface, Focus is a minor entry in Smith’s filmography. And while the level of intrigue between the actor and his costar Margot Robbie is far more memorable than the film itself, this outing saw Big Will at a bit of a crossroads. Released in 2015, Smith was coming off a string of failures that were getting pretty embarrassing from a critical perspective. He tried young adult sci-fi and came back for a third Men in Black sequel after his role in prestige pictures started to fade. At this point, it had been eight years since his last bonafide hit.
By taking a chance with this duplicitous thriller, Smith was reigniting his sex appeal and his ability to engage with an adult audience. As Nicky, a conman who has a penchant for gambling indulgences, he straddles the line between magnetic romantic lead and a complete degenerate. Despite the film’s mismanaged twists and turns, the sheer power of watching Smith and Robbie’s emotional tango makes it far too enticing to look away. This was a welcome return to form for Smith, who manages to thrive as an unlikeable character.
Best Line: “Attention is like a spotlight … and our job is to dance in the darkness.”
09. Mike Lowery
Bad Boys (1995)
At the tail end of The Fresh Prince of Bel Air, Smith began to seriously contemplate what his post-television career would look like. He’d just starred in the drama Six Degrees of Separation (1993) as a con artist, but he needed a persona that took advantage of his natural qualities. To his advantage came Michael Bay’s Bad Boys, where the sky is never blue, it’s orange. Bay’s debut film marked Smith’s fourth and his first action flick. Still green, components of his Fresh Prince character pervades Bad Boys’ Mike Lowery: He’s a smooth talking lady’s man.
Furthermore, he’s far more derogatory than Smith’s cultivated wholesome image. Lowery dodges bullets, fiery explosions, and ex-lovers while he and his partner Marcus Burnett (Martin Lawrence) solve a heist, take down a drug kingpin, and protect a witness. Smith often thrives when he has a foil, and Lawrence bounces off the young star easily as the two trade barbs, even while supporting one another. The movie proved Smith’s ability to carry a soon-to-be franchise—and served as the first sketch of the “Big Willie” template.
Best Line: “Now that’s how you drive! From now on… That’s how you drive!”
08. Chris Gardner
The Pursuit of Happyness (2006)
The Pursuit of Happyness marked Smith’s first collaboration with Italian director Gabrielle Muccino, who he teamed up with again in 2008 on the strangely misguided Seven Pounds. As he was maturing as a performer and into the realm of prestige filmmaking, Happyness earned Smith his second Oscar nomination and provided the opportunity to collaborate with his then-eight-year-old son Jaden. It’s easy to see what drew Smith to this material as a father himself; he will do anything to make sure his family name is advanced. Now that provides a whole different context reading into his celebrity status, versus the simplicity of a father scrounging to pay his rent.
In 2006 the family drama packed a real wallop in the emotional baggage department with Smith operating outside of his normal wheelhouse by playing an everyman named Chris Gardner, who has a serious financial situation on his hands. When the film lays on the schmaltz a little thick, it’s Smith’s portrayal of Gardner that elevates the material into his most relatable role to date. With every poor financial decision Gardner makes, Muccino and Smith never pass judgment as the film sheds any ounce of cynicism lurking at its core. Their collaboration finds a balance between overly earnest and improbable, to being genuinely affecting. He knows that crying on the floor of a public bathroom while holding your adolescent son will cue the waterworks from his audience.
At this point in his career, the general movie-going public was like putty in his hands.
Best Line : “Maybe happiness is something we can only pursue. And maybe we can never actually have it…no matter what.”
07. Robert Clayton Dean
Enemy of the State (1998)
By 1998, Smith had played young hotshots who matured over the course of the narrative, like Hiller (Independence Day), Jay (Men in Black), and Lowery (Bad Boys). In Tony Scott’s spy action-thriller Enemy of the State, Smith portrays Robert Clayton Dean—a married father and labor lawyer. After unwittingly being embroiled in a high-stakes murder of a Congressman, the NSA destroys his life in a bid to discredit the murder evidence he holds. He loses his job, wife, and bank accounts—in a film that explores the dangers of a surveillance state.
Unlike his previous roles — a pilot, cop, and an undercover agent for a secret organization — the character is supremely out of his depth, bumbling against a corrupt government agency using surveillance trackers. Scott pairs the young Smith with the veteran Gene Hackman, who plays an off-the-radar tech expert Brill. Copying the dynamic between the young actor and Tommy Lee Jones in Men in Black (1997), the two display a cranky but endearing chemistry. Here, Smith’s heroism isn’t born through innate skill; he learns and adapts from an everyman to a novice techie. His most mature role would foreshadow his later dramatic turns in Ali (2001) and The Pursuit of Happyness (2006).
Best Line: “I’m sick of this. You either shoot me, or tell me what the hell is going on!”
06. Robert Neville
I Am Legend (2007)
There are a couple of ways to look at I Am Legend. With a movie star at its center, it works as a high concept whirlwind about the last living man on earth, surrounded by bloodsucking shells of our former selves. But you can also look at as a cerebral transgressive blockbuster that rests its laurels on dissecting power dynamics and asking the timeless question, “Who are the real monsters?”
Either way, Smith found success as brooding scientist Robert Neville, whose virus has left the human race extinct. All that remains of his identity is a capable German Shepard named Sam and daily trips to the video store, where he talks to mannequins. While solitude is certainly bliss, Smith finds emotional weight while grappling with his own mistakes and his new place in this world.
Smith plays Neville as a man hellbent on atoning his sins. Francis Lawrence’s direction brings a cinematic scope to a film that has to inorganically create tension, and while Akiva Goldsman’s script nearly derails the process at every turn, Smith holds it all together. At 101 minutes, this is one of Smith’s most efficient films that begs its viewers to let go of the past, and step into the future.
Best Line: “Don’t worry about a thing because every little thing gonna be alright.” True this is a song lyric, but Smith mumbles this Bob Marley ditty in a sobering scene alongside his dog.
05. Captain Steven Hiller
Independence Day (1996)
Though Smith had already established himself as a household name, his performance as Capt. Steven Hiller—a fighter pilot who teams up with genius David Levinson (Jeff Goldblum) to combat an invading alien force—is the classic Will Smith performance.
Roland Emmerich’s Independence Day perfectly captures the magic and charisma that would make Smith into a superstar. In it, he steals a chopper, flies an interstellar ship, and punches an alien in the face. Confident, squeaky clean, and achingly cool, the role signaled the “young hotshot” ethos that would define Smith’s career in a mix of comedic, action, heroic, and dramatic chops.
The Smith/aliens combo worked so well, he took on a similar construct in his 1997 follow-up, Men in Black.
Best Line: “This was supposed to be my weekend off, but noooo, you got me out here, draggin’ your heavy ass through the burning desert, with your dreadlocks sticking out the back of my parachute. You gotta come down here with an attitude, actin’ all big and bad. And what the hell is that smell? I coulda been at a barbecue, but I ain’t mad.”
Six Degrees of Separation (1993)
There’s something strange and quietly special about Smith’s performance in Six Degrees of Separation. The stage play turned into a film had the actor working in the realm of high-brow humor with a splash of Woody Allen’s version of New York. His role as Paul, a con man who infiltrates a group of Fifth Avenue socialites under the guise of being the son of Sidney Poitier with a pitch for the movie version of Cats in hand (oddly predicting a nightmarish future), is his most daring and complex work to date.
The accompanying cast includes a murderers’ row of performers approaching the twilight of their careers including Donald Sutherland, Stockard Channing, and Ian McKellen going toe to toe with a burgeoning talent who was only known as a novelty rapper and sitcom star. It’s an impressive feat to say the least watching Smith, who in actuality was a skillful lyricist in his own right create rhythmic poetry with an already juicy screenplay.
This is the only time Smith has played an overtly queer character. He crafted a portrait of a person who feels ostracized from the world, and who tries to create a reality that would foster opportunity where he otherwise would not be accepted. Paul is ready to compete in a society that rewards survival of the fittest, and Smith’s performance complements the intellect by pushing knowledge to the point of being outright sexy.
Best Line: “Why is life in the 20th century so focused on the very beginning and very end of life? What about the 80 years we have to live between those two inexorable bookends?”
The Fresh Prince of Bel-Air (1990-96)
No television program has ever introduced an actor better than the Fresh Prince of Bel-Air ushered in Will Smith. The character’s name is Will, and “in west Philadelphia born and raised,” the literal Philli-native raps over the series’ theme. And through 148 episodes, audiences were treated to the actor’s musical talents, dancing skills, comedic timing, and effortless cool. The recurring role also set a precedent for the majority of his characters during the first phase of his career (again, hot shots maturing), in addition to his uncanny ability to play off his costars, particularly father figures like Uncle Phil (James Avery).
Two episodes, in particular, combine father figures and maturity. In Season 4, “Papa’s Got a Brand New Excuse”, Will’s father returns, and Will desperately craves his dad’s affection, even to the point of rebelling against Uncle Phil. But when his dad runs out on him again, he’s left collapsing into Avery’s arms asking, “How come he don’t want me?”, in a heartbreaking display of dramatic emotion.
Later, in the series finale — whose final shot of Will staring at an empty living room has now become iconic through memes — Will says goodbye to the family and his surrogate father Uncle Phil. Will is still charming, but also an adult. He chooses not to be transient or irresponsible anymore; he decides to remain in California to earn his Bachelor’s degree. Looking back, the entire arc of Fresh Prince of Bel-Air perfectly introduces a young actor, carefully displays and grows his best abilities, and sets him off to graduate to greater success.
Best Line: Carlton Banks: “I thought Ashley was in bed.” Will: “Yeah, and you also thought Tupac Shakur was a Jewish holiday.”
02. Agent J
Men In Black (1997)
The Summer of 1997 had Smith caught in the middle of a career transition that would catapult him into a new stratosphere of fame. This was his gap year in between the conclusion of The Fresh Prince of Bel-Air in 1996 and his platinum selling album Big Willie Style in 1998. So, naturally, Smith used this time to jump into his second science fiction film in as many years. Men In Black is arguably Smith’s most iconic film performance. While it may not be his most profound piece of work, the franchise sparked a distinct look that, for better or worse, makes its way into many Halloween wardrobes.
This would mark the beginning of Smith’s four collaborations with director Barry Sonnenfeld. While he’s not a movie star that thrives on working with auteur directors, per se, Smith found a nice groove living in an alternative universe where your bodega man could be an alien undercover. As the hotshot agent in training “J”, Smith settled in as a family-friendly loudmouth, complete with one-liners and displaying a physicality that ran the gamut of slapstick comedy to action star. In one scene he’s jumping across buildings, and in the next, he’s getting vomited on by an infant extraterrestrial.
In many ways, Smith was breaking boundaries as far as representation on screen, while still finding room to subvert expectations. If there was anything that plotted the course for the bulk of Smith’s career, it was that sleek black suit and Ray-bans.
Best Line: “The difference between you and me, I make this look good.” This line my come off as a bit corny today, but this was Smith’s coming out party. His announcement that a new presence in blockbuster cinema was dawning.
01. Muhammed Ali
“The champ is here!”
Captain Hiller might be Smith’s signature role, but his best performance remains Muhammed Ali for Michael Mann’s 2001 biopic of the famed boxer. Throughout most of his career, Smith’s typically played some semblance of himself and relied on his natural traits. While the historic pugilist possessed many of those same attributes, be it charm, swagger, or humor, Ali stands as one of the rare examples of Smith immersing himself into a character.
For one, he had to learn Ali’s fighting style. In every boxing match, the actor displays the fighter’s signature head movements, the hands positioned too low (daring the opponent to charge), the strut, and the muscle. Smith studied Ali’s cadence and vocal intonations, turning in an uncanny resemblance, too. For many, the heavyweight champion was a God, but Smith plays him as a flawed, insecure human. It’s in these more quiet, introspective scenes — such as Ali ruminating on his future with the Nation of Islam — that say as much about the man as any boisterous rhyme or fight.
This approach required nerve on the part of the actor, and given Ali’s importance as a historical figure and emblem of pride and courage, Smith’s never taken on a role with as much pressure to get it right — and Smith does. He is Ali. And through which, he became an Oscar nominee.
Best Line: “I ain’t draft dodging. I ain’t burning no flag. I ain’t running to Canada. I’m staying right here. You want to send me to jail? Fine, you go right ahead. I’ve been in jail for 400 years. I could be there for four or five more, but I ain’t going no 10,000 miles to help murder and kill other poor people. If I want to die, I’ll die right here, right now, fightin’ you, if I want to die. You my enemy, not no Chinese, no Vietcong, no Japanese. You my opposer when I want freedom. You my opposer when I want justice. You my opposer when I want equality. Want me to go somewhere and fight for you? You won’t even stand up for me right here in America, for my rights and my religious beliefs. You won’t even stand up for my rights here at home.”