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->''"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.

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!!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)

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!!Related Tropes:

* ADateWithRosiePalms: Examined in excruciating detail during the closing minutes of ''Deep in the Heart of Texas'' where Dave discusses how he must gauge the quality and length of his potential masturbation sessions by estimating how long his family will be out of the house. Then, following the requisite shame of the aftermath, depending on how messy the result is, he may sometimes have the family dog come in to lap up the evidence.
* AffectionateParody: His typical "white man" accent is proper, lilted, and oftentimes affable in the face of whatever pretentiousness or faux pas said character will soon be involved with.
* BrickJoke: In ''The Age of Spin''. [[BlackComedyRape "He rapes, but he saves!"]]
* BrokenPedestal: Subverted in regards to BillCosby as seen [[https://www.youtube.com/watch?v=vdJJRPf1x_U here]].
* 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.
* CynicismCatalyst: ''The Age of Spin'' has him talk about how his generation was raised on progressive television shows such as the CareBears that taught them that positive emotions, understanding, and acceptance alone could win the day only to be despondent when they found out that wasn't the case. However, while he was disappointed that while it was impossible for him "to shoot love out of his chest" like a Care Bear, he has since then "shot love ONTO somebody's chest."
* {{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]].
* DrugsAreBad: He smokes weed, but a lot of his stories involving it have him imperiled because of his usage such as his infamous two-night show in Detroit.
* DudeShesLikeInAComa: Played with. Dave talks about "The Mercy Jerk" in one of his specials, wherein instead of badgering their wives for some late-night sex, husbands will quietly go to the bathroom to masturbate if their spouses look too tired or don't seem to be in the mood. However, he doesn't see anything wrong with jacking it to his wife's toes if she forgot to wear socks to bed because in his opinion, "you can't rape feet."
* InsultBackfire: He recounts his wife calling him "a pussy" in front of company and then turning it around by admitting that he is "a pussy" in the sense that he's "soft and warm and persuasive" like "a pussy" and that if she doesn't take care of him, then he'll start to stink "like (her) pussy."
* KarmaHoudini: While driving home with a friend, they were pulled over with his pal being arrested for refusing to take a breathalyzer test. Not wanting to waste time in the police station just so he could be transported to where he wanted to go hours later, Dave decided to do the breathalyzer test himself (a feat the officer at hand thought ill-adviced since his friend claimed to be his designated driver) to prove he was stable enough to drive home...and passed. Not because he was sober, but because the device was meant to detect alcohol, not marijuana.
* LargeHam: Most of his characters are loud, boisterous, and have a tendency to do a lot of yelling.
* ManlyGay: He was once accused of attacking the "masculinity" of homosexual men with his gags. He points out that "fucking another guy in the ass" is "the most gangster shit" he's ever heard about.
* 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.
* MisaimedFandom: He partly defends Manny Pacquiao's views on the LGBT community, not necessarily because they're right, but because he finds it incredulous that after America "bombed the masculinity" out of much of Asia, that homosexuals and transgenders would consider an anomaly of outright Filipino machismo as "(their) champ."
* 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.
* NeverLiveItDown: Every night, whenever she goes to bed earlier than him, his wife tells Dave not to eat the lunches she packed for their kids because of how he used to take big bites out of them to cure his munchies while everyone else in the house was asleep, culminating in his son punching one of his schoolmates in the face because he wrongly believed she was the one eating his meals behind his back.
* StopBeingStereotypical: In ''Killing Them Softly'' he was taken aback when a waiter automatically assumed he would order the friend chicken in a restaurant just because of his ethnicity. He entered a brief HeroicBSOD as he considered that perhaps instead of eating chicken because it was delicious, he ate it because he was genetically predisposed to enjoy it...right before eating the chicken anyway.
* SympathyForTheDevil: For O.J. Simpson, who Dave believes to be guilty, but nonetheless admires for his athletic feats. During his second and third encounters with him anyway.
* 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.

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