The character Clayton Bigsby was inspired by Dave Chappelle's maternal grandfather. He was a blind Caucasian who was abandoned as a baby and raised by African Americans. Because of his upbringing and his inability to see himself, he considered himself to be African American.
Dave Chappelle did not show up to shoot the scene in which Clayton Bigsby gives his speech. He instead appeared on Howard Stern's radio show and sat with Stern for hours. Assistant director Chip Signore called in to the show and told Chappelle on the air to come to work.
The black friend that Dave says was offended by the Clayton Bigsby sketch is graphic designer Cey Adams who is best known for his work with Beastie Boys.
Mel Brooks's Blazing Saddles (1974) featured a black Sheriff who dresses in a Klan costume. Dave Chappelle worked with Brooks on Robin Hood: Men in Tights (1993) and becomes Sheriff at the end.