Grammys Flashback '98: Willie Gets Jokey Wit It

Will Smith has become such a prominent actor that you might have forgotten that his career in entertainment began in the music industry as a rapper. With rap music in its early stages, Smith earned some of the genre's earliest Grammys. In the pressroom for his most recent Grammy, Smith couldn't help but turn the stage into a stand-up routine.

At the 1998 Grammys, the then-29-year-old actor and rapper won the Best Solo Performance Grammy for "Gettin' Jiggy Wit It," an award that he had also won the previous year ("Men in Black"). Alongside close friend DJ Jazzy Jeff, with whom Smith had previously won two Grammys for their hip-hop duo DJ Jazzy Jeff & The Fresh Prince, Smith harkens back to his comedic ways on The Fresh Prince of Bel-Air.

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As he intermittently sends the pressroom into a frenzy of laughter, Smith also talks on a more serious note about rap music and the relative novelty of the genre in the industry. Despite his joking nature, Smith explains what the award, his fourth Grammy, means to him.

Although he is "hyped" to have received the award, the Philadelphia native admits to doubting himself and being "almost scared of making music again" for Big Willie Style until Jada Pinkett, whom he had married the previous year, inspired him "to keep going and do it for real."

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"It was ten years ago the first time that we (Smith and Jazzy) were nominated and there were a couple of times in those ten years that we kind of thought that was pretty much it, it's over," he adds. "It just feels good 'cause rap in really its first cycle of infancy, so we don't know what...a rapper's longevity [is]....We don't know what the cycle is yet, so [it] feels good to be continuing."

Smith would receive two additional Grammy nominations in the following two years but he wouldn't continue his Grammy saga despite albums in 2002 and 2005.

Watching the video, you could say the man enjoyed the moment while it lasted.