When the music industry introduced Will Smith to the world as the Fresh Prince, folks had little idea that it was also the launchpad for a young man who would become one of the most successful entertainers to hit Hollywood. Whether he was making us laugh or blaming the wind for the tears in our eyes with his Oscar-nominated performances, Will Smith proved to the critics that he was more than just a rapper from Philadelphia. In a field where talent is everything, Smith has exhibited time after time that he can master both comedic as well as dramatic roles, a rarity in Hollywood. In anticipation of his latest film, I Am Legend, here’s a list of his best roles to date.

Fresh Prince of Bel-Air (Will Smith, 1990-1996) In West Philadelphia born and raised, on the playgrounds is where he spent most of his days. When the show debuted in September of 1990, people were skeptical about what he could bring to the table. After all, he was just some wacky rapper with about a dozen hits and a Grammy Award winner. He couldn’t be an actor they thought. The sitcom proved to be a stepping-stone for the soon-to-be Hollywood star and the show is still causing laughs from syndication and the DVD.

Six Degrees of Separation (Paul, 1993) Although it didn’t get a lot of attention, Smith also showed his potential as a young actor who possessed a hunger to hit big. His role as a lying, conniving but mentally ill homosexual reached new heights for the novice actor and was an early showcase of his potential.