His television show on Comedy Central broke many television stereotypes of African Americans. At the time his show premiered, Cosby had cleaned up negative self images of African-Americans. Chappelle, reversed the Cosby effect by challenging conventional wisdom regarding African American stereotypes. His show allowed an African-American to reflect honestly about race and inequality while using humor as a backdrop. So many characters reflected negative stereotypes instead of sweeping them under the carpet like Cosby had tried to do.
The show reached huge numbers, and then Dave disappeared for 10 years. While many speculated why he left his craft, he never felt the need to explain to anyone his reasons for taking time for himself. I truly respect that his absence remained a mystery. Dave has been slowly reintroducing himself to the millennials. His most recent work is 2 episodes on Netflix. The shows are live comedy shows. There are no comedy sketches like his previous television show. We just get Dave with a live audience. However his humor is just as irreverent as the TV show.
In the first episode, he discusses a wide range of issues. His fame seems to be a backdrop for some of the skits. My favorite comedy bit is O.J. Simpson. He splits up O.J. into 2 eras. He draws some comedic analogies with O.J. that are introspective and funny. Within this episode he also jokes about another African-American legend, Bill Cosby. He has an ability to reflect that their guilt is inconsequential to their body of work. In a sense, they are the first African-Americans to benefit from wealth and status when it comes to our nation's criminal justice system. Such a subtle play on history. I thought it was genius. The second episode is filmed in Austin Texas. Again, Dave uses humor to discuss topics that many simply would avoid. He can cross cultural lines that many comedians do not have the ability to do in their performances. He can talk and joke about sexuality, misogynist behavior, race and culture using analogies that are honest and funny. They also make some uncomfortable and cause them to reflect upon their own values. This is why Chappelle matters. His humor uses high level thinking to get across viewpoints using low brow humor. Simply put, Chappelle's humor makes us think about our thoughts and actions, which is why I recommend his body of work.