Critically acclaimed throughout its run, the series often satirized and examined—through dark and racial humor—race, social stereotypes, masculinity, celebrity culture, and comedy itself.
[1] The show opened with Chappelle being introduced over the instrumental from the song "Hip-Hop", from the album Let's Get Free by Dead Prez.
Chappelle performed sketches that premiered intricate cultural topics, such as prostitution, the entertainment industry, gun violence, numerous drug references (particularly marijuana, alcohol, PCP, crystal meth and crack cocaine) and music.
[2] Many guest stars appeared on the show, including Half Baked co-stars Guillermo Díaz, Jim Breuer and Snoop Dogg (who was also a musical guest); RZA, GZA and Method Man of the Wu-Tang Clan, Rick James, Damon Dash, Redman, Ice-T, Arsenio Hall, Wayne Brady (the only guest to appear on stage), Mos Def (who was also a musical guest), Eddie Griffin, Susan Sarandon, Q-Tip, Rashida Jones, Jamie Foxx, Carson Daly, Ron Jeremy, Bill Burr, Patrice O’Neal, Rich Vos, Spike Lee, Michael Rapaport and Joe Rogan.
Musical guests included De La Soul, Ludacris, Robert Petkoff, Talib Kweli, Fat Joe, Wyclef Jean, Killer Mike, Big Boi of OutKast, Anthony Hamilton, Kanye West, Common, DMX, Busta Rhymes, Slum Village, John Mayer, Questlove, Cee-Lo Green, Vida Guerra, Erykah Badu and Lil Jon.
According to Neal Brennan in the season-two DVD commentary, the production team never edited in prerecorded laughs, with the exception of the "Dude's Night Out" sketch due to the lack of reaction from the audience.
He stated that he disliked working "20 hours a day" and that the popularity of the show was making it difficult for him to continue his stand-up career which was "the most important thing" to him.
This date was pushed back to May 31, 2005, when production fell behind schedule in December 2004 because, according to Comedy Central, Chappelle had fallen ill with the flu.
[18] On May 14, Time announced that one of their reporters, Christopher John Farley, had interviewed Chappelle in South Africa, and that no psychiatric treatments were occurring or necessary.
Chappelle returned shortly thereafter and quelled rumors of psychiatric or substance-abuse problems, and emphasized that his trip was a "spiritual retreat" intended to keep his sense of reality outside the bubble of intense pressure and fame and to keep his humor fresh.
[19] Chappelle would say that he was unhappy with the direction the show had taken, and expressed in an interview with Time magazine his need for reflection in the face of tremendous stress: Coming here, I don't have the distractions of fame.
[20]On July 14, Comedy Central president Doug Herzog announced that Chappelle was welcome back any time, but that the comedian had said he was still not ready to return.
Around the same time came confirmation from Comedy Central that co-creator Neal Brennan had left the show,[21] and it was later revealed a rift had formed between him and Chappelle.
On February 3, 2006, Chappelle made his first television interview since production ceased on season three, on The Oprah Winfrey Show.
Chappelle was interviewed for Inside the Actors Studio on December 18, 2005, at Pace University's Michael Schimmel Center for the Arts.
As of 2005, the first-season DVD was the best-selling TV series set of all time,[33] beating out other popular shows such as The Simpsons (the first season of which held the record beforehand), American Dad!, Family Guy, Friends, and Seinfeld.
On June 5, 2007, Comedy Central released a compilation DVD titled The Best of Chappelle's Show which highlights 25 of the most popular sketches in all seasons.
However, less than two months later, the series was removed from both services following Chappelle's commentary concerning his lack of royalties from the show during his appearance on Saturday Night Live.
[43][44] Despite the renegotiated deal, Season 3 (the "lost episodes") were not reposted to Netflix, and has also been withdrawn from other platforms where it was available previously like Crave in Canada.