Dave Chappelle has been an enigma the last few years. After famously walking away from his wildly popular show on Comedy Central Chappelle has largely remained out of the public eye. More recently the comedian began playing a series of unannounced shows throughout the country that while sparking significant hype have been terribly disappointing.
That is a shame because I still find Chappelle to be one of the finest stand up comics. Ever. Recent public flops aside his two specials, Killing Them Softly and For What It’s Worth, remain two of my favorite specials of all time.
Though not necessarily a political comedian Chappelle does occasionally touch upon politicians, especially those who might be linked to the Black experience. Long before Barack Obama became the nation’s first black president comedians like Cedric the Entertainer opined about Bill Clinton being the de facto first one.
The clip here is from 2000 right near the end of the Clinton Administration. There are some timely references to then President Clinton’s candor and coolness that those who saw his recent rave review at this year’s Democratic National Convention will find timeless as well. And since Chappelle initially cut his comedy chops as a teenager at the Washington D.C. improv in the late 80’s there is always room for a well placed mayor joke as well.
See any similarities with the persona here with what we saw during the Democratic Convention?