Chappelle's Show

The show opens with Chappelle being introduced over the instrumental from the song "Hip-Hop", from the album Let's Get Free by Dead Prez. Chappelle performs a short stand up in front of a live audience. The focus then shifts to a prerecorded sketch. The show is notorious for its handling of the topic of sexuality and Chappelle's casual usage of racial epithets. 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. The show sometimes ends with a musical performance by a hip hop or soul artist.[2]

Rather than acting out sketches in front of a live studio audience, the sketches were prerecorded with the audience reaction usually used in lieu of a laugh track. According to Neal Brennan in the season-two DVD commentary, the production team never edits in prerecorded laughs, with the exception of the "Dude's Night Out" sketch due to the lack of reaction from the audience.[3]

• A Moment in the Life of Lil Jon – Chappelle plays rapper/producer Lil Jon doing normal, everyday tasks, with a vocabulary consisting of almost nothing but the words 'Yeah!', 'HWHAT?!', and 'O-kay!' The real Lil Jon appeared in one sketch opposite Chappelle's character, with Lil Jon speaking in an excessively dignified accent. The rapper credited the sketch with increasing his visibility.[4] Entertainment Weekly put it on its end-of-the-decade, "best-of" list, saying, " We could have filled this list with 100 reasons we miss Chappelle's Show, but the biggest one would have to be his riotous celebrity impressions."[5]
• Charlie Murphy's True Hollywood Stories – Charlie Murphy (who also wrote the sketches) retells his encounters with 1980s celebrities, the most popular being the Rick James story. The sketch features Murphy as himself and Chappelle as James, including incidents such as James slapping Murphy and referring to him as 'Darkness', interspersed with cuts from an interview with the actual present-day Rick James, trying to cover up for his past behavior, saying, "Cocaine's a hell of a drug."[6] The sketch spawned one of the show's popular catchphrases, "I'm Rick James, bitch!", which Chappelle, as James, repeatedly declares. The sketch attained even greater public attention when, in 2005, a candidate for city council in Hattiesburg, Mississippi, also named Rick James but unrelated to the singer, had many of his "Vote Rick James" campaign signs defaced by writing "Vote Rick James bitch!" or stolen by fans of the sketch.[7][8] The other "True Hollywood Story" depicted Murphy and his crew losing a pickup game of basketball against Prince. Both James and Prince confirmed the stories were true, with James's admission coming in unreleased interview footage produced for the skit. Prince's confirmation came in an interview with MTV, in which he stated "The whupping is true".[9] Prince later used an image of Chappelle dressed as Prince as the cover of his single "Breakfast Can Wait".
• Frontline – A spoof of the PBS series of the same name, it was hosted by Kent Wallace (played by William Bogert). The first Frontline sketch, "Blind Supremacy", featured the life of Clayton Bigsby (played by Chappelle), a blind white supremacist who is not aware that he is actually a black man. Grantland.com writer Rembert Brown deemed this sketch the winner of his "Best Chappelle Sketch Ever", beating out the Wayne Brady sketch in his 64-sketch, NCAA Tournament style bracket. This sketch was part of the first episode and garnered attention for its extensive use of the word "nigger" (mostly spoken by Chappelle's character).[10] The sketch has been compared to the iconic "word association" Saturday Night Live sketch from 1975 featuring Chevy Chase and Richard Pryor[11] which received similar reactions for its use of the word. Charlie Sheen stated that he was hospitalized in 2010 as a result of developing a hernia from laughing so hard upon viewing the sketch.[12] Other Frontline sketches featured stories of racist animal actors and gay versions of everything from the DMV to the KKK.
• Racial Draft – A parody of modern-day pro-sports drafts. Various multiracial or multiethnic celebrities such as Tiger Woods (Chappelle), Lenny Kravitz, the Wu-Tang Clan (playing themselves), O. J. Simpson, Eminem and Madonna were "drafted" into a (potentially) entirely different race, based on their perceived ethnicity or some other cultural appropriations in their act or lifestyle. Elián González was recertified as Hispanic, after being culturally appropriated by white America. Lenny Kravitz was declared 100% Jewish, the Wu-Tang Clan 100% Asian, and Tiger Woods 100% black. Chappelle also played the white announcer/representative, while rapper Mos Def played the black representative; radio personality Angie Martinez played the Hispanic representative.
• WacArnold's – Chappelle gets a job as a young man at a fast-food restaurant that portrays itself as providing a community service by offering jobs to disenfranchised, poor youth. A scene-by-scene mock of a 1990 McDonald's commercial is followed by Chappelle slowly realizing the job is embarrassing and he does not make enough money to support his family. He gets robbed and harassed on his way to work. During one encounter in the last scene of the sketch, a thug (played by Donnell Rawlings) quips, "Hey Calvin! It's a fine line between fries and shakes!" before he breaks into song, "The leanest burger in the world, could be the meanest burger in the world, if you cook it that way!". He follows by stating he has to "stop smoking this shit here" as his friends break out in laughter. The song is a remake of a 1971 song by The Persuaders (also covered by The Pretenders in 1983 and H-Town in 1996) "Thin Line Between Love and Hate".
• Wayne Brady's Show – After Dave Chappelle quits the show in an opening segment that coincidentally mirrored the contract negotiations for the aborted third season, Wayne Brady (portraying himself) takes over as host and is asked to emcee the remaining episodes of the series since Chappelle had already filmed the remaining sketches. Regretting the decision to leave the show, Chappelle returns and confronts Brady. The ensuing confrontation leads to the airing of a flashback to a night of misadventures involving the two that portrays Brady (contrary to his friendly public image) as a murderous, pimping, and seriously disturbed sociopath in the mold of Denzel Washington's character Alonzo Harris from the film Training Day.[13] Brady had trouble filming the sketch, finding it difficult to say the line "Is Wayne Brady gonna have to choke a bitch?".[14]
• When Keeping It Real Goes Wrong – A documentary style sketch, it serves as a cautionary tale about when not to "keep it real" (be completely honest). The sketch depicts events in which a character is just minding his business until someone else says or does something that the first character does not like. The character is given a choice: ignore the alleged provocation, or "keep it real" (get confrontational and be antagonistic with whoever provoked him), with the character going with the latter, all the while boasting about how they "keep it real". Eventually, the character's decision backfires severely on him, thus ruining his life, while the person who provoked him is having the time of his life, and the character's friends shun the character's choice to "keep it real".
• Player Hater's Ball – Guest starring Ice-T, the sketch featured Chappelle and several other regulars attending a convention of "haters", i.e. people who make hurtful and deprecating comments towards others. The characters all dressed and acted in the manner of flamboyant 1970s pimps. The convention featured an award for "hater of the year" and an ad-libbed segment where the attendees were shown pictures of celebrities such as Rosie O'Donnell and Kelly Osbourne and delivered put downs. This later spawned a sequel called "Haters in Time" where the haters went back in time to when the Africans were slaves and end up killing one of the slave masters.
• Samuel L. Jackson Beer – Filmed as a long-form ad, the sketch featured a parody of Samuel Adams Beer sponsored by actor Samuel L. Jackson. Chappelle appeared as Jackson, wearing a wig reminiscent of the actor's hair style in the 1994 movie Pulp Fiction and dressed in Revolutionary War-era garb similar to the spokesman who had recently appeared in Samuel Adams Beer ads. Chappelle's performance played heavily on Jackson's propensity for roles which involve angry shouting and copious profanity. At one point when asked to stop yelling by Bill Burr, Chappelle, as Jackson, yells "No, I can't stop yelling, 'cause that's how I talk! You ain't never seen my movies?"

• Tron Carter (played by Chappelle) – a cocaine dealer, he is originally shown in a sketch where he has received reparations for slavery and due to a "hot hand in a dice game" becomes the richest man in America. When asked about the infant he carts around in a stroller, Tron says, "I just bought this baby, cash." He is also one of the roommates in The Mad Real World. Later in a spoof of Law & Order, Tron gets the same lenient treatment as those involved in white-collar crime, invoking the "fif" in response to every question. Tron also appeared in the first episode of season three in a sketch in which he described an altercation with Method Man and was tortured by the methods described in the song "Method Man" from Enter the Wu-Tang (36 Chambers). In the reparations episode, he is shown gambling in Brooklyn and described as a Harlem resident, but in another episode, he is shown in his house on "Everglade Boulevard" bagging up cocaine and watching the fictitious R. Kelly music video "Piss on You", and he receives a phone call from the Dade County Police Department, suggesting he lives in Miami.
• Negrodamus – Paul Mooney plays a black prophet and fortune teller (a satire of Nostradamus). In the sketch, people (mostly white) ask him various questions such as "Negrodamus, why do white people love Wayne Brady so much?" to which he replies "White people love Wayne Brady because he makes...Bryant Gumbel look like Malcolm X." (This clip was later shown as a drug hallucination in the Wayne Brady sketch.)[14]
• Tyrone Biggums – Chappelle plays a squeaky-voiced crack addict recognized by his white, blistered lips and constant scratching. His first appearance was in the second episode of season one. He is often heard saying, "I smoke rocks" and "SHAZAM!" Tyrone enjoys eating peanut butter and crack sandwiches, and was the spokesman for "Red Balls", an energy drink made from cocaine. He also made an appearance in a Fear Factor spoof sketch on the "Wayne Brady's Show" episode, wherein he was exceptionally willing to do gross challenges, and was nonreactive to the hot coals underneath his feet, which lit his big toenail on fire (the same fire from which he would later light a cigarette). Tyrone Biggums was featured in "The World's Greatest Wars" segment where he was a cellmate of River Terrace Crew leader General Cornrow Wallace (Mos Def).
• "Silky" Johnson (played by Chappelle) – A notorious player hater, he won the fictitious "Hater of the Year" award twice (one of which was for calling a bomb threat on the Special Olympics), and who later traveled back in time to "hate" in the past.
• Chuck Taylor (played by Chappelle) – The lead "white" anchor on the fictitious "News 3", he is played by Chappelle in whiteface makeup and a blonde wig. Taylor has appeared in a few sketches, the first of which was the "Reparations" sketch from season one.
• Leonard Washington (played by Chappelle) – Washington first appeared in the first-season sketch "Trading Spouses", wherein he acted as the patriarch of a white family for a month. Notably, when entering rooms unfamiliar to him, Washington looks out the windows to see if he is being followed. He also expressed his displeasure that many white families do not use washcloths when taking a shower or bath. One of the only things that can make Leonard Washington back down is being shot. When asked for his hometown in the "World Series of Dice" sketch, Washington replied, "Where I'm from? A little town called none ya goddamn bidness." He has a wife and a son, T-Mart. He is seemingly unaware of white culture, unknowing of Renée Zellweger (as he stated in "Trading Spouses" after reading White People Magazine).
• Ashy Larry (played by Donnell Rawlings) – A shirtless black man with flaky-white skin and chapped lips, he is always seen wearing a pair of white boxer shorts. He appeared in the "World Series of Dice" sketch, in one of Chappelle's daydreams during a boring dinner conversation, and was seen holding Dave Chappelle's $50 million check in one of the lost episodes. Ashy Larry is also one of the names Wayne Brady calls the PCP he gives to Dave in the Wayne Brady sketch. Rawlings briefly reprised his role as Ashy Larry in the sketch comedy show, In The Flow with Affion Crockett, encountering Chappelle (played by Crockett).
• Robot Dancing Man – Set designer Karl Lake did the robot dance in random places, including a barbershop, club, and a courtroom (in a deleted scene). In the sketches, he is generally not acknowledged, despite the out-of-place behavior, nor does he acknowledge anyone. A few exceptions to this rule have occurred. One of them is during the "Slow-Motion" sketch, in the club, when Dave acknowledges him by saying "The Robot", and emulating him. Another is when Wayne Brady "takes over" the show, during one of the commercial break introductions; Wayne is looking at Robot Man's moves, and proceeds to dance with him. Also, in the opening theme for season three, Charlie Murphy and Donnell Rawlings have hogtied and taken the place of the two men who start off the show. Robot Man is seen in the background doing his dance and the harmonica player yells out "Robot, help us!", but to no avail.

Many guest stars have 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 include 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.

Reruns have frequently aired on Comedy Central and VH1 in the US. The series also airs around the world, with episodes airing on MTV in Germany, Comedy Central in Brazil, The Comedy Network and MuchMusic in Canada, SBS,[19] NITV[20] (sister channel to SBS), The Comedy Channel and 7mate in Australia, and FX in the United Kingdom. The series was also shown on WGN America and was syndicated to various television stations across the US, including MyNetworkTV.

The series is available to be streamed on the Comedy Central app and website. The series is also available to stream on Paramount+, Netflix, and HBO Max.[21][22][23][24] It is free to digitally rent with select public libraries in the United States through Hoopla.[25]

On November 1, 2020, the series became available to stream on Netflix and HBO Max. 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.[26][27] On February 11, 2021, Chappelle announced that he had renegotiated his deal with ViacomCBS, and the show returned to the services the following day.[28][29] 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.[30][31]

The DVD sets for seasons one and two of Chappelle's Show have sold extremely well since their release. As of 2005, the first-season DVD was the best-selling TV series set of all time,[32] 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.

The episode "Music Jump-Off" which featured Chappelle visiting his old high school, the Duke Ellington School of the Arts, intercut with previously unaired sketches and musical performances, did not make either DVD set.

On October 11, 2005, the first half of the first season was released on UMD.

On May 23, 2006, the first uncensored season was made available for purchase on the iTunes Music Store, and on June 20, the second uncensored season was also made available on iTunes.

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.

On November 20, 2007, Comedy Central released a boxset with season one, season two, and "the Lost Episodes" titled Chappelle's Show – The Series Collection.

All box sets were released by Paramount Home Entertainment (under the Comedy Central banner).

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