Over the course of an illustrious career, Will Smith has embedded himself into the Hollywood pantheon with a series of iconic performances. 30 years after he burst into the public consciousness via our speakers, he and DJ Jazzy Jeff’s exuberant, radio-appeasing rap accounts for just one component of his overarching legacy these days. For less incorrigible actors, the role-- and remuneration-- of The Fresh Prince Of Bel Air would’ve allowed them to rest on their laurels but if anything, Smith has upped the intensity of his workload on a year-by-year basis.

Initially conceived as a way to pay off his exorbitant tax bills, an onscreen role that got the IRS off his back soon morphed into a lifelong vocation for the Philly native and his bankable charisma would lead to countless high-powered roles in the years to come. Yet for every Agent J, Detective Mike Lowry or Capt. Steven Hiller of the United States Marine Corps, there are those characters that didn’t translate to the big screen as well as Will had hoped or ended up consigned to the wrong side of his box office record books. Poised to take theatres by storm with sequels to Bright and Bad Boys respectively, as well as undertaking the very unenviable role of trying to fill Robin Williams’ shoes in Aladdin, it’s worth gearing up for his return by looking at some of his less lauded roles.

Where The Day Takes You

Flanked by an all-star cast that included Lara Flynn Boyle, Ricki Lake, Sean Astin, Balthazar Getty and Alyssa Milano, 1992’s Where The Day Takes You marked Will Smith’s inaugural appearance on the big screen. Directed by Marc Rocco, the film follows the plights of a group of teenage ne’er-do-wells and runaways on the streets of LA as they make their way through a maze of drugs, prostitution and vagrancy. In a striking contrast to the action heroes that he’d soon embody, Will is tasked with the portrayal of Manny, a wisecracking paraplegic who has to endure a brutal beating from Peter Dobson’s Tommy Ray. A gritty precursor to future coming-of-age films such as Kids and Mid-90s, it has aged remarkably well for a film that was a box office flop.

Six Degrees of Separation

A year after he played a supporting role amid an ensemble of Hollywood’s hotly tipped talent, Will would get his chance to strike out on his own with Six Degrees Of Separation. Adapted from the John Guare play of the same name, the film sees Will play the role of seasoned hustler that infiltrates the shallow ranks of the New York intelligentsia by posing as the son of Sidney Poitier. Through a series of elaborate falsehoods, ‘Paul’ gains the trust of two affluent but ultimately closeminded art dealers and sets the stage for a movie that addresses issues around race, sexuality, discrimination and the overarching humanity that should bind us all together.

Enemy Of The State

Due to his box office acclaim, it’s not often that the words ‘underrated’ and ‘Will Smith’ are reconcilable with one another. However, it’s a more than appropriate descriptor for his turn in 1998’s Enemy Of The State. Fresh from the first entry in the Men In Black series, the late Tony Scott’s tale of a man in the wrong place at the wrong time reworked Smith as an average joe that had been led out of his depth. Framed for a crime and an adulterous affair that he didn’t partake in, labor lawyer Robert Clayton Dean must scrape and claw to clear his name with any espionage skills at his disposal. A thrilling tale of deception, underlying agendas and corruptive power of surveillance, it’s a film that is often left by the wayside when conversation turns to outstanding thrillers and, in many ways, forewarned of the NSA whistleblowing scandals to come.

The Legend Of Bagger Vance

Derived from Hindu scripture in the Bhagavad Gita, Will Smith and Matt Damon took the leap into the realm of parable in The Legend Of Bagger Vance. Derided by some as schmaltzy and overly sentimental, Robert Redford’s take on the Steven Pressfield novel struck a discordant note for many but Will’s performance is captivating nonetheless. Acting as a spiritual guru for a man at the end of his tether, Smith’s take on the mythical figure wasn’t too much of a stretch considering the wholesomeness that was ascribed to him but he deserves credit for it nonetheless.

Jersey Girl

Not content to share a screen with just one writer of the Oscar-winning Good Will Hunting, Will Smith has also dispensed life advice to Ben Affleck in Jersey Girl. As opposed to playing a messianic being, his cameo in this Kevin Smith flick sees Will play himself in a uniquely meta moment. Perched beside Affleck’s Ollie in a waiting room at a time of personal crises, the man that once took umbrage with the fact that ‘Parents Just Don’t Understand’ imparts some words of familial wisdom to the music promoter. Complete with a touching remark about “how it takes everything I’ve got” to leave his family behind for the day, it’s a role that is of pivotal importance to the story and the dialogue could’ve easily been culled from Will’s real life. Not to mention it features the comedic relief of Will referring to himself as “hung, like… It’s ridiculous.”

Seven Pounds

With a whopping budget of an estimated $55,000,000, Seven Pounds had all the makings of one of those life-affirming Hollywood classics but never attained the widespread culture resonance that it clearly strived for. Labeled a masterpiece by some and a damp squib by others, the film follows Smith as IRS agent Ben Thomas as he attempts to change lives and make reparations for a tragedy in his past. Cast as the mysterious benefactor, Smith does an excellent job of conveying the film’s heavy subject matter with skill and avoids the ham-fisted pitfalls that his character could’ve fell into in the hands of a less capable man.

A Winter’s Tale 

Hailed as one of the most endearing figures in Hollywood, Will’s seamless transition into a YouTuber tells you just how much people gravitate towards him as a media personality let alone an actor. For that reason alone, his portrayal of an entirely more malevolent figure in A Winter’s Tale is worth a watch. Patchily received to say the very least, the adapted screenplay of Mark Helprin’s magnum opus was listed as one of those ‘unfilmable’ projects for countless years before Akiva Goldsman decided to step up to the plate. Boasting a 14% approval rating on Rotten Tomatoes, Will’s portrayal of a brooding and pragmatic Lucifer is not only the highlight of the film but also marks one of the few times that he’s ever ventured in the territory of the antagonist.

After Earth

Whie many of these films are unfairly maligned or overlooked, 2013’s After Earth is one film that Will and Jaden Smith would be more than willing to resign to the depths of the past. Conceived as a sci-fi epic, it follows the aftermath of Nova Prime’s Cypher and Katai’s unceremonious arrival on the remains of their ancestral home planet. Crafted by M Night Shymalan during his career’s emphatic downturn, many believed the film to be thinly-veiled scientology propaganda and Smith has since labeled the debacle as “the most painful failure of my career.” Released around the same time as his father’s cancer diagnosis, Smith came out of the other side with a new perspective on the world around him:

“That Monday started the new phase of my life, a new concept: Only love is going to fill that hole. You can’t win enough, you can’t have enough money, you can’t succeed enough. There is not enough. The only thing that will ever satiate that existential thirst is love. And I just remember that day I made the shift from wanting to be a winner to wanting to have the most powerful, deep and beautiful relationships I could possibly have.”