Trivia: Chappelle's Show
- Artist Disillusionment / Creator Backlash: As he said in response to fans constantly quoting his most famous line out of context:
Chappelle: "You know why my show is good? Because the network officials say you're not smart enough to get what I'm doing, and every day I fight for you. I tell them how smart you are. Turns out, I was wrong. You people are stupid."
- Big Name Fan: On the Season 2 DVD commentary, Chappelle relays a story of Martin Scorsese coming up to him one time and saying he was a fan of his show. His favorite sketch? "The Playa Haters Ball".
- Colbert Bump: By the early 2000s, Rick James had been disgraced thanks to drug arrests and a 3-year prison sentence. Then Dave Chappelle spoofed his life and Rick's popularity reached new heights.
- 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.
- Defictionalization: Sort of. The "Trading Spouses" sketch was meant to make fun of the Reality TV craze. A little while later ABC announced that they were going to do an American version of Wife Swap. A couple of weeks before it's debut, Fox premiered Trading Spouses: Meet Your New Mommy, and ABC accused them of ripping off their show.
- A Rick James comedy biopic was apparently in the works for some time, with Chappelle reprising his role; James' death put a stop to it.
- 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. The DVDs, despite being huge sellers, ultimately fell out of print for a couple of years. In 2012 Comedy Central reissued the entire series as a box set.
- Life Imitates Art: The final skit of the show's "third season" (filmed before Dave left) has Dave meeting with The All Powerful Show Business, who offers him various ways to capitalize on his popularity (i.e. Dave Chappelle cereal, a Lil Jon movie and an MTV Cribs appearance). The skit ends with Dave walking away from show business.
- Similarly, after appearing on the series, Wayne Brady landed a multi-episode stint on the FX show "Dirt", playing an Affably Evil employee for a murderous rap mogul who threatens to castrate one of the cast members and force-feed them their own penis. Not to mention breaking a basketball player's kneecaps.
- The famous Wayne Brady episode opens with a prologue segment in which Dave Chappelle "quits" the show due to the insane filming schedule and Executive Meddling. Even on the DVD Commentary, he admits that the schedule line was very true.
- 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.
- Orphaned Series: After Comedy Central aired the filmed sketches for season three, Dave Chappelle pretty much disowned the show outright (up until they announced they would air the filmed sketches, Chappelle claimed that he was open to coming back but the decision to air those sketches burnt those bridges).