Chappelle’s Show is an American sketch comedy television series created by comedians Dave Chappelle and Neal Brennan, with Chappelle hosting the show and starring in the majority of its sketches. Chappelle, Brennan, and Michele Armour were the show’s executive producers. The series premiered on January 22, 2003, on the American cable television network Comedy Central. The show ran for two complete seasons. An abbreviated third season of three episodes aired in 2006, compiled of previously unreleased sketches.
After numerous delays, production of the third season of the show was abruptly ended when Chappelle left the show. TV Guide included it on their list of “TV’s Top 100 Shows” and it also was placed at number 26 on Entertainment Weekly‘s “New TV Classics” list. Throughout its run, the show was critically acclaimed.
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.
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.
- 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.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.”
- 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.” 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. 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”. 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 Frontline, 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 blindwhite 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). The sketch has been compared to the iconic “word association” Saturday Night Live sketch from 1975 featuring Chevy Chase and Richard Pryor 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. 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 psychopath in the mold of Denzel Washington‘s character Alonzo Harris from the film Training Day. Brady had trouble filming the sketch, finding it difficult to say the line, “Is Wayne Brady gonna have to choke a bitch?”.
- 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?”