This Philly rapper-actor made an instant impact with his crossover hit "Parents Just Don't Understand." The Grammy award–winning single — rap's first — set the stage for the charismatic wordsmith to make his transition to acting as the star of the popular long-running sitcom, The Fresh Prince of Bel Air. Hip hop culture was given a primetime slot on a national stage thanks to the sitcom. And in its wake, Smith has become one of the highest paid, most bankable leading men in Hollywood.
(Photo: Camilla Morandi / Corbis/As featured in Hip Hop: A Cultural Odyssey)