Dave Chappelle

Dave Chappelle's Comedy Central show was the most popular and important sketch comedy show since the early days of Saturday Night Live. The comedian's relaxed, country-bumpkin demeanor and apparent affability provided a nice contrast to the maniacally aggressive stage presence of predecessors Richard Pryor and Lenny Bruce. Though no less insightful or incendiary, Chappelle's humor hid behind the veneer of this casualness, which perhaps made Chappelle's brand of racial humor a lot easier for Middle America to stomach. This charm would prove to be a double-edged sword, and after only two seasons Chappelle (much like Frank Zappa) came to believe that his audience was applauding for the wrong reasons. He took flight to Africa in an attempt to reconnect and rejuvenate, and afterwards returned to stand-up comedy. Like Chris Rock, Chappelle was always a champion of hip-hop and neo-soul music. His 2004 Brooklyn "Block Party" event featured some of urban entertainment's most critically acclaimed artists. The proceedings were captured for posterity and resulted in a popular concert film.