->''"The hardest thing to do is to be true to yourself, especially when everybody is watching."''

'''Dave Chappelle''' was born on August 24, 1973 in Washington, D.C. His first credited role was in Creator/MelBrooks' ''Film/RobinHoodMenInTights'' as "Ahchoo." He was offered the chance to star as Bubba in ''Film/ForrestGump'', but he turned down the role, [[ItWillNeverCatchOn believing that the movie would flop at the box office]] (a decision he would come to regret). Chappelle wrote and starred in the classic stoner film ''Film/HalfBaked''. He is best known, however, for his sketch comedy show on Comedy Central named (appropriately) ''Series/ChappellesShow''. The show lasted from 2003 to 2006. During this time he came out with several sketches that enjoyed wide success--most famously in which Chappelle plays a disorderly Rick James, driving the phrase "I'm Rick James, bitch!" [[MemeticMutation deep into American culture]]. Chappelle received two Emmy nominations for his show.

Chapelle's career abruptly ended when he decided the fame was becoming too much and people were laughing at his jokes [[MinstrelShows for the wrong reasons]]. He took an unannounced sabbatical in South Africa and then returned home to spend time with his family. He has appeared on stand up stages, talk shows, and occasional independent projects, but he has had [[CelebrityIsOverrated no desire to reclaim the fame]] he walked away from at its height.

Chappelle started a comeback in late 2016 by hosting ''Series/SaturdayNightLive'', an episode which was acclaimed for being a welcome breather from the particularly nasty 2016 presidential election. Memorable moments included a collaboration with Creator/ChrisRock for an election night skit, a parody of ''Series/TheWalkingDead'' featuring Chappelle as BigBad Negan threatening his classic characters, and a "Last Call" sketch with series regular Creator/KateMcKinnon. This was followed by an intense bidding war by various networks to air new stand-up specials from Chappelle, with Netflix ultimately shelling out $60 million for the rights of two unreleased shows and a third to be produced in 2017.

!!Roles of Note:

* ''Film/RobinHoodMenInTights'' (1993): Ahchoo
* ''Film/TheNuttyProfessor'' (1996): Reggie
* ''Film/ConAir'' (1997): Pinball
* ''Film/HalfBaked'' (1998): Thurgood
* ''{{HBO}} Comedy Half Hour'' (1998)
* ''Killing Them Softly'' (2000; comedy special)
* ''Film/UndercoverBrother'' (2002): Conspiracy Brother
* ''Series/ChappellesShow'' (2003-2006)
* ''For What It's Worth'' (2004; comedy special)
* ''Block Party'' (2005): AsHimself
* Netflix specials: ''The Age of Spin'' (2016), ''Deep in the Heart of Texas'' (2016), and an unnamed 2017 special (stand-up)

!!Related Tropes:

* BrickJoke: In ''The Age of Spin''. [[BlackComedyRape "He rapes, but he saves!"]]
* CatchPhrase: Becoming a PhraseCatcher for his own show bits led in part to his hiatus in Africa.
* CelebrityIsOverrated: He prefers a quiet life on a ranch in Ohio than being rich and famous.
* {{Deconstruction}}: His notable skill is in going through what might be seen as StockShticks, exploring their origins, highlighting the potential ridiculousness/justification behind such ideas/notions, and subsequently come out with a meaningful statement on RealLife dynamics and social questions. [[SubvertedTrope That is, if]] [[CrossesTheLineTwice he doesn't go off on a further tangent and take it back to hilarious]].
* LargeHam: Most of his characters are loud, boisterous, and have a tendency to do a lot of yelling.
* MarsAndVenusGenderContrast: Chappelle does tend to go through the usual motions/gags involved in the dating game, sex and marriage, although he does go out of his way of further questioning these stereotypes while at the same time pointing out the origins of why men, women and other genders hold on to those anyway.
* NWordPrivileges: Chappelle explored the word on many different levels, pushing what was OK to say on TV and diving into the culture behind it. When people started treating the word casually because of how mainstream his work had become, he was very taken aback.
* ThisIsForEmphasisBitch: Many of his most famous sketches included punctuated curses: "I'm Rick James, Bitch!" "[[Creator/SamuelLJackson Sam Jackson's]] beer! It'll get you drunk! Mmm mmm, bitch!"
* UncleTomfoolery: One of the reasons he decided to end his show was because people were starting to see his characters this way. Instead of making fun of the stereotypes and showing how ridiculous they were, people were laughing ''at'' the stereotype.
* WhiteLikeMe: One of his recurring bits was to dress or talk as an "average white man" to play on white stereotypes.