- The original opening theme was supposed to have lyrics, but the "band" couldn't synch the lyrics to the music. Dave told them to just keep saying "Chappelle's Show" over and over.
- The original sketches pitched for a pilot were Popcopy, Clayton Bigsby, and Reparations.
- Somewhere in every episode of the second season, the same man can be seen intensely dancing "The Robot". He is Karl Lake, set dresser for the show. In the first season, he was asked to be in a crowd scene and do something funny. Chappelle liked the dance Lake was doing and made it a fixture of the second season.
- All of Paul Mooney's lines are improvised.
- Dave Chappelle left the show abruptly during filming of the third season. He later stated in interviews that he never intended to make a third season but he felt pressured by Comedy Central and his co-workers to continue. Comedy Central pulled the show from its 2005 schedule and decided to shelve the completed sketches in hopes that Chappelle would return to finish the season. Chappelle stated in interviews that if Comedy Central aired the episodes he would definitely not return to the show. After negotiations with Chappelle stalled, Comedy Central decided to repackage some of the completed sketches and air them in 2006. Charles Q. Murphy and Donnell Rawlings took over the hosting duties.
- Dave Chappelle was inspired to create the show after watching a documentary about Hugh M. Hefner that featured clips of "Playboy After Dark" (1969). Chappelle was inspired by the laid-back atmosphere of Hefner's show.
- After returning from his spiritual trip to Africa, Dave Chappelle has since expressed distaste for the show, as well as losing his partnership with writer Neal Brennan.
- During a stand-up performance in Sacramento, CA, Chappelle ended it abruptly after berating the audience for repeating the show's catchphrases and having difficulties with his career.
- The Beastie Boys taped a performance of their 1986 song "The New Style" for the third season. But the segment did not air.
- According to Neal Brennan, noted political comedian Mort Sahl was offered a role in a sketch but he turned it down. The sketch was never shot.
- Sketches were shot for the aborted third season but did not air including: - A parody of Michael Jackson's videos Thriller (1983) (TV) and "Beat It" referencing his child molestation trial - A parody of Super Size Me called "Maximize Me" - A sequel to Daddy Day Care starring Charlie Murphy - Dave uses the speech patterns of politicians to receive special treatment at a coffee shop and a strip club - A parody of the Virgin Mobile commercials featuring two singers on the street - A "Hip-Hop Newsbreak" portraying the lyrics of Nas's "If I Ruled the World" - Dave imagines what would what happen if he sold a ringtone and spoke at the Republican National Convention - A "Hip-Hop Newsbreak" stating lyrics of Dr. Dre's "Still D.R.E." - Dave harasses his ex-girlfriend's husband at his job at a donut shop - A "Hip-Hop Newsbreak" stating lyrics of Das Efx's "They Want EFX"
- A performance by John Legend doing his song "Ordinary People" was shot for the third season but did not air.
- The song that plays when Chappelle walks on stage is "Hip-Hop" by Dead Prez. The group shot a performance of the song for the third season but it did not air.
- Paul Mooney originally wanted Negrodamus to be named "Niggadamus". But Chappelle felt that Comedy Central would not allow that to air.
- Charles Q. Murphy first showed the infamous Rick James sketch to his brother Eddie Murphy before audience tapings. Eddie enjoyed the sketch so much that the two watched it again.
- The character of 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. So because of his upbringing and his inability to see himself, he considered himself African-American.
- The Popcopy sketch was inspired by a bad experience Neal Brennan had at a Kinko's.
- 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.
- In "The Mad Real World Sketch", most of Chappelle's lines were improvised. Also, the part where Tron, Tyree, and Faze run when they hear a siren was not planned. A siren just happened to go off while filming.
- "The Mad Real World" was inspired by David Edwards's experience on the second season of The Real World. Edwards was kicked out of the house by the other cast members. Edwards is a friend of Chappelle's and Chappelle helped Edwards to become a cast member on the series.
- In the "Blackzilla" sketch, there is Japanese writing on a window in one shot. In English, it translates to "white devil".
- Most of the lines in the "Playa Haters Ball" sketch were improvised.
- Donnell Rawlings speaks Korean in the "Playa Haters Ball" sketch. Rawlings really speaks Korean having learned it in the U.S. Air Force while stationed in South Korea.
- Donnell Rawlings came up with his character, Beautiful, just minutes before the sketch was to begin filming. After he quickly got the wig and clothes, he looked in the mirror and said "Man, I feel beautiful!"
- For "The Racial Draft" sketch, a scene was filmed with an actor portraying 'Elian Gonzalez' saying that he wanted to return to America. But it was deleted.
- In "The Niggar Family" sketch, Chappelle improvised the part where he pops back into the Niggars' kitchen.
- According to Chappelle, the use of sparse sets for the "Rick James" sketch was inspired by the Family Ties episode "Family Ties" (1982) {A, My Name Is Alex: Part 2 (#5.24)}.
- Charles Q. Murphy was originally filmed telling the story while sitting down. But Neal Brennan realized that by having Murphy stand it would give the scenes more energy.
- Charles Q. Murphy's son plays Eddie Murphy in the "Rick James" sketch.
- Dave Chappelle and Neal Brennan learned about the Prince story from Rick James (II). During James' interview for the previous episode, he told the story about the basketball game between Charles Q. Murphy and Prince. They asked Murphy to tell the story on-camera and the sketch was quickly put together.
