• Creator Backlash: Dave left the show mostly due to the way he felt the racial humor had gone, the fanbase that refused to stop repeating his famous line and how Comedy Central treated the show. This is Chappelle's spin on it, however. The fact that he had gone from stuff like...Half Baked... to becoming a cultural icon in less than five years might have been a bit too much for him to take in all at once.
    • Dave also said that he didn't believe the third season could possibly live up to the hype of his 50 Million dollar contract, it should be noted that he tried to keep the contract a secret from the media and was upset to see the headline in the newspaper.
  • Executive Meddling: One of the reasons Dave quit was all the fights with the network.
    • In particular: they wanted more Catch Phrase-type sketches and fratboy humor.
  • Hey, It's That Guy! / Retroactive Recognition: Cee Lo Green performs on one episode, introduced as just "Cee Lo" and long before the release of "Fuck You".
    • That appearance happened almost a decade after his first album was released.
  • Keep Circulating the Tapes: The DVDs lack about half of the live musical performances. However, since Comedy Central reruns the show periodically, it shouldn't be too hard to find this material.
  • Missing Episode: The entire "third season" (hosted by Charlie Murphy and Donnell Rawlings, two of the show's writers and actors) was advertised as "The Lost Episodes", which aired two years after the second season and consisted of skits Dave Chappelle was filming before he left the show. Chappelle was displeased with the airing of these skits, as they were mostly unfinished and offensive, particularly the "Racial Pixie" sketch.
    • Season two also had an episode based around "lost sketches", that were filmed but ultimately not aired at that point. In particular, one sketch, a sequel to the season one "Player Haters Ball" was only partially shown.
  • Shout-Out: Both editions of Charlie Murphy's True Hollywood Stories contained numerous references to both Rick James and Prince's careers.

Charlie: [while playing basketball] Hey Prince, man, you got a towel? It's kinda hot out here.
Prince: Why don't you purify yourself, in the waters of Lake Minnetonka?