Hollywood Shuffle is a series that celebrates our cultural icons in film and television whose performances have resonated with generations of viewers. From the pioneering actors and actresses who’ve helped break barriers and pave the way for those to follow, to the most promising and decorated thespians of today, their dedication to their craft is respected and appreciated.

Award-winning actor Will Smith’s foray into Hollywood began as a byproduct of his music career. The Philadelphia native parlayed his popularity as one-half of the duo DJ Jazzy Jeff & the Fresh Prince into a starring role in the hit television series The Fresh Prince of Bel-Air. Portraying a fictionalized character loosely based on himself, Smith’s performance yielded high ratings and rave reviews, prompting the film industry to knock at his door.

After appearing in his first feature film, Where the Day Takes You, in 1992, Smith went on to become one of the most bankable leading men in history, with roles ranging from an action hero to that of an everyman. With various box office hits under his belt and more accolades than one trophy case can fit, one piece of hardware that has eluded Smith thus far is an Academy Award, particularly for Best Actor. Not for any lack of effort of his own as he’s already been up for the award twice, in 2002 and 2007.

However, Smith’s fortunes could change on Sunday (March 27) at the 94th Academy Awards. For the third time in his career, he’s been nominated again for the Best Actor In A Leading Role category for his portrayal of Richard Williams—father of tennis legends Venus and Serena Williams—in the 2021 biopic King Richard. The film, which is also nominated for Best Picture, has dominated the film awards circuit, making the role his most praiseworthy to date. If he were to secure a victory, it would further solidify a resume that’s already earned him the distinction of not only one of the greatest actors of his time but also a living legend.

In this edition of The Hollywood Shuffle, VIBE looks back on the 10 iconic roles that have defined Will Smith’s career.