7. Dave Chappelle
Best known for his comedy show The Chappelle Show, Dave Chappelle retired when he was at the peak of his career. He is also known for big screen roles in movies such as Robin Hood: Men in Tights and Con Air. He also had a starring role in Half Baked. He is listed as one of Comedy Central’s “100 Greatest Stand-Ups of All Time.” Chappelle does occasional stand-up shows still and has had a couple of surprise shows over the past couple months, but mostly stays quiet living with his family. While rumors circulated that he left television because of drug problems, Chappelle told Oprah Winfrey he had had issues with how the entertainment industries portrayed black entertainers.
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