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"I can’t even tell something true unless there’s a punchline behind it."

David Khari Webber Chappelle (born August 24, 1973 in Washington, D.C.) is an American stand-up comedian, actor, writer, and producer who achieved worldwide fame as the co-creator and host of the Comedy Central variety show named (appropriately) Chappelle's Show, and has gone on to be considered one of the greatest comedians of his generation.

As far as early work goes, Chappelle's first credited role was in Mel Brooks' Robin Hood: Men in Tights as "Ahchoo". He was offered the chance to star as Bubba in Forrest Gump, but he turned down the role, believing that the movie would flop at the box office (a decision he would come to regret). He also co-wrote and starred in the stoner comedy film Half Baked.

Chappelle's Show was far and away Chappelle's claim to fame on a mainstream scale. The show ran for two seasons from 2003 to 2006, becoming a massive critical and ratings hit by its latter season, netting Chappelle two Emmy nominations, and cementing him in the annals of 21st-century popular culture through memes and quotes derived from his sketches that are still referenced to this day.

However, amid anticipation of a third season of the show, Chappelle suddenly went missing and resurfaced in South Africa. As the world would later find out, he had decided that the fame was becoming too much, a conclusion driven heavily by Comedy Central getting involved in the show's production and him feeling that his mostly white fanbase was laughing at his jokes for the wrong reasons. He made appearances at stand-up stages, on talk shows, and in occasional independent projects, but he generally showed no desire to reclaim the fame — and the $50 million a third season would've secured — that he walked away from at its height.

Chappelle started a comeback in late 2016 by hosting Saturday Night Live, an episode which was acclaimed for being a welcome breather from the particularly nasty 2016 presidential election. Memorable moments included a lengthy opening monologue reflecting on the election’s outcome, a collaboration with Chris Rock for an election night skit, a parody of The Walking Dead featuring Chappelle as Big Bad Negan as well as a returning number of his iconic show characters, and a "Last Call" sketch with series regular Kate McKinnon. 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 produced in 2017.

In October of 2019, as a tribute to his decades of wit, integrity, societal reflections, and impact on American culture, he received the Mark Twain Prize for American Humor, presented to him at the Kennedy Center for Performing Arts. The award ceremony was broadcast on PBS, and can be partially viewed here.


Works of note:


Chappelle's work shows examples of:

  • Affectionate Parody: 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.
  • Brick Joke: In The Age of Spin. "He rapes, but he saves!"
  • Broken Bird: His father died when he was struggling to make it in show business and when he finally made it, he faced a lot of personal struggles that led him to become more reclusive since.
  • Broken Pedestal: Subverted in regards to Bill Cosby as seen here.
  • Call-Back: During his 8:46 special, he quotes a line he said decades earlier from a stand-up special for a more serious effect: "Do we give a fuck what Ja Rule thinks [at a time like this]?"
  • Catchphrase: Becoming a Phrase Catcher for his own show bits led in part to his hiatus in Africa.
  • Celebrity Is Overrated: He prefers a quiet life on a ranch in Ohio than being rich and famous.
  • Character Tics: Slapping the microphone against his thigh when he finds any of his own jokes particularly funny. In the Netflix specials, he sometimes runs his hand down the buttons on his done-up jacket when giving a monologue. He'll also occasionally hold his fingers up to his lips as if holding a cigarette, due to his years as a smoker.
  • Creator Backlash: He stands by the material created for Chapelle's Show but his disillusionment came from how people would take satire at face value. Especially with the use of Black Face.
  • Corpsing: Does this quite a bit in the Netflix specials.
  • Cynicism Catalyst: The Age of Spin has him talk about how his generation was raised on progressive television shows such as the Care Bears (1980s) 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."
  • Darker and Edgier:
    • His half-hour special 8:46 is easily his most raw special to date. It has some jokes, but the majority of it has Chappelle in deep anger and pain as he speaks about the murder of George Floyd, the wider history of police brutality against African-Americans, and the uncanny connections the situation has to his personal life.
    • His second filmed 2020 special, Unforgiven, is even less joke-prevalent. It deals with events during his childhood career of him getting screwed over by others, which he compares to how Comedy Central treated him over Chappelle's Show, sending him in a deep rage over how they licensed his show to Netflix and HBO Max with him not getting a cent over it (though he made it clear that it wasn't the money but the lack of respect he received that made him furious).
  • Deconstruction: His notable skill is in going through what might be seen as Stock Jokes, exploring their origins, highlighting the potential ridiculousness/justification behind such ideas/notions, and subsequently come out with a meaningful statement on Real Life dynamics and social questions. That is, if he doesn't go off on a further tangent and take it back to hilarious.
    • At one point he deconstructs cartoons and kids' shows, comparing Pepé Le Pew's constantly unwanted advances to sexual assault and calling Sesame Street a very unsafe neighborhood filled with strange animals, on top of teaching kids to label people through their treatment of Oscar, who is homeless and has every right to be grouchy about it.
  • Dragged into Drag: Discussed in his 2006 interview with Oprah Winfrey, where he recounts the time he refused to do a Disguised in Drag scene for a movie, with the writers, producers, and director trying to pressure him into relenting. He suggests that Hollywood likes putting black actors in drag scenes because it's a way of forcing them to humiliate themselves.
  • Drugs Are Bad: 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.
    • Its also notable that Dave will almost always portray any drug other than weed in an entirely negative light, such as his awful mushroom experience or the Squick laden Tyrone Biggums character.
  • Dude, She's Like in a Coma: 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."
  • Fetish: Related to the above, Dave Chappelle has joked about how he has a foot fetish.
  • Fridge Logic: Played With for laughs in his bit on Jussie Smollett.note  Chappelle noted that if Smollett's alleged attackers had in fact been racist, homophobic white men, then they would never watch a show with a predominantly black cast and queer representation like Empire in the first place.
    Chappelle: So, where were you going. (beat) Subway? (beat) Sandwiches?!
  • Green-Eyed Monster: He has expressed mild, if playful, envy of the relative swiftness of the LGBTQ+ community's societal progress (decades), only for him to have the audacity to complain about it not going fast enough when African-Americans had to endure centuries of protracted discrimination to attain similar basic civil rights.
    • Also playfully brought up when he went to see fellow comedian Kevin Hart together with his son.
  • Groin Attack: "So I kicked her in the pussy!". That was the punchline he worked up for when talking about what he did as a child when the mother of his friend didn't have enough Stovetop Stuffing for everyone.
  • I Am Not Spock: During his stand-up on Michael Richards' racist rant, Chappelle kept calling him Kramer.
  • Insult Backfire: 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."
  • Karma Houdini: 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.
  • Large Ham: Most of his characters are loud, boisterous, and have a tendency to do a lot of yelling.
  • Manly Gay: 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.
  • Mars and Venus Gender Contrast: 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.
  • Misery Poker: Brought up in the Age of Spin special which Dave calls "comparative suffering".
  • N-Word Privileges: Chappelle has 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.
  • Once Done, Never Forgotten: 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.
  • Orphaned Punchline: Inverted. Chappelle claims that truly experienced comedians can come up with punchlines first and then create jokes around them, essentially a reversal of the usual process. To support this claim, he provides the example of "So I kicked her in the pussy!" and proceeds to create a gag for it to cap off. Twice.
  • Rage Breaking Point: Played for Laughs when he describes how he got so sick of people coming up to him and saying "I'm Rick James, bitch!" when he was with his family in Disney World, culminating with him punching the head off the last person who said it to him that day. And that person? Mickey Mouse!
    Dave: Gasp! I can't believe that Mickey Mouse is a Mexican!
  • Reclusive Artist: Famously disappeared for months after leaving Chappelle's Show abruptly, only for people to learn he went to Africa to try and avoid media attention. In an interview with Oprah he said he loves being famous but was disillusioned with how the entertainment empire was trying to control him, as no one paid attention to him until it became evident he was worth something.
  • Running Gag: In The Age of Spin, the four times Dave met O.J. Simpson — the last of which was told after his final punchline.
  • Stop Being Stereotypical: In Killing Them Softly, he notes that he was taken aback when a waiter automatically assumed he would order the fried chicken in a restaurant just because of his ethnicity (and he was right). Chappelle entered a brief Heroic BSoD 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.
  • Sympathy for the Devil: 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.
    Sharon: How could you?... How could you shake hands with that murderer?!
    Dave: Sharon, with all due respect... that murderer ran for over 11,000 yards.
  • This Is for Emphasis, Bitch!: Many of his most famous sketches included punctuated curses.
    "I'm Rick James, bitch!"
    "Sam Jackson's beer! It'll get you drunk! Mmm-mmm, bitch!"
  • Uncle Tomfoolery: 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.
  • What You Are in the Dark: This trope is why he'd be reluctant to ever call 911, since those messages have a tendency to find their way to national television if the cases related to them are grisly enough. Understandably, no one would be all too focused on talking in a dignified or courageous manner during such a call, but Dave is still worried that if he perished regardless, his friends would bemoan how he "died crying like a bitch."
  • White Gangbangers: Dave discusses Token White gang members in one of his specials, saying that the white thug is probably the worst out of all of them, since he had to do something to gain the black members' trust. He also says that the white gang bangers are there to talk to the police when something bad happens.
    "You'll be walking down the street and you'll see a bunch of black dudes walking, not just any old black dudes, we're talking 'thugs'. And in the group, they got one, or two, sometimes as many as three white guys with them, you ever seen that shit? Well let me tell you something about those white guys. Those white guys are the most dangerous motherfuckers in them groups. It's true, man. There's no telling what kind of crazy shit they've done to get them black dudes' respect, but I'll tell you they've done some wild shit.'"
  • White Like Me: One of his recurring bits was to dress or talk as an "average white man" to play on white stereotypes.


 
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The N-Word Family

One of Chappelle's more interesting skits involves a 1950's middle-class white family with a very unfortunate surname.

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