Funniest Dave Chappelle bits as new stand-up special hits Netflix

December 4, 2022 | WTOP's Jason Fraley recalls Dave Chappelle's best bits (Jason Fraley)

WASHINGTON — No comedian in recent memory has created so many pop-culture staples in so short a time with such stellar satire on race relations.

Now, the 21st century’s funniest comedian is officially back, as Dave Chappelle returns for a much-anticipated stand-up comedy special streaming exclusively on Netflix starting Tuesday, March 21.

It weaves together two live gigs from Chappelle’s vault: “The Age of Spin” from March 2016 at Los Angeles’ Hollywood Palladium and “Deep in the Heart of Texas” from April 2015 in Austin, Texas.

The trailer shows Chappelle spitting jokes about the rise of ISIS, meeting O.J. Simpson shortly before the murder of Nicole Brown Simpson, and how the biggest threat to black men is actually salt intake.

The double-stand-up performance is Chappelle’s first comedy special in 12 years, part of a reported $60 million deal with Netflix that will also see a third comedy special arrive in the coming months.

Along with his postelection hosting of “Saturday Night Live” back in November 2016, this marks Chappelle’s long-awaited return after infamously walking away from a reported $50 million offer from Comedy Central for a third season of his hit sketch-comedy series “Chappelle’s Show” in 2005.

His return is doubly exciting for D.C. folks, as Chappelle was born in the nation’s capital in 1973 and graduated from Washington’s Duke Ellington School of the Arts in 1991. Before long, he landed film roles in “Robin Hood: Men in Tights” (1993), “The Nutty Professor” (1996) and “Blue Streak” (1999).

Still, it was Comedy Central’s “Chappelle’s Show” (2003) that made him an instant comedy legend, thanks to laugh-out-loud bits that spoke volumes about society with truly daring social commentary.

So, as you gear up to watch the Netflix special, what were the funniest bits from “Chappelle’s Show?”

Click through the gallery below for the hilarious countdown!

WARNING: Videos contain explicit material, including racial slurs, for purposes of social commentary.

Introduction What are the funniest sketches from “Chappelle’s Show?” Click through the gallery for our Top 20 countdown. WARNING: Videos contain explicit material, including racial slurs, for purposes of social commentary.
20. ‘Samuel L. Jackson Beer’ Best Line: “Yes, they deserve to die! And I hope they burn in hell!”
19. ‘Tron Carter’s Law and Order’ Best Line: “I plead the Fif! 1-2-3-4-Fif!”
18. ‘When Keeping it Real Goes Wrong Brenda Johnson’ Best Line: “I don’t like people playing on my phone!”
17. ‘The Player Haters Ball’ Best Line: “He’s got dolphin teeth! Arsenio Hall teeth!”
16. ‘Reparations 2003’ Best Line: “Nah, I just bought that baby cash.”
15. ‘Celebrity Jury Trial Selection’ Best Line: “Michael Jackson has many faces. None of them look guilty to me.”
14. ‘A Moment in the Life of Lil Jon’ Best Line: “Yeah!!” “What!!” “Okay!!”
13. ‘The N***** Family’ Best Line: “We’re rich, they’re N***** rich.”
12. ‘I Know Black People’ Game Show Best Line: “Is pimping easy?” “Hell yeah.” “That is correct.”
11. ‘Making the Band’ Best Line: “Who are the five best rappers? Dylan, Dylan, Dylan, Dylan and Dylan. I spit hot fire.”
10. ‘Tupac is Still Alive’ Best Line: “I wrote this song in ’94.”
9. ‘Mad Real World’ Best Line: “Lysol and Tyree are just genuinely nice guys.”
8. ‘Black Howard Dean’ Best Line: “Byah!!!”
7. ‘R. Kelly’s P*** On You’ Video Best Line: “Your body’s a port-a-potty.”
6. ‘Charlie Murphy’s True Hollywood Stories — Prince’ Best Line: “Shoot the J! Shoot it! In your face, Charlie Murphy.”

Racial Draft - Natural Selection of the Millenia from Kato on Vimeo.

5. ‘The Racial Draft’ Best Line: “I’ve always wanted to say this … For shizzle.”
4. ‘Wayne Brady’ Best Line: “Is Wayne Brady gonna have to choke a b****?”
3. ‘Tyrone Biggums — Fear Factor’ Best Line: “I smoke rocks, Joe Rogan!”
2. ‘Charlie Murphy’s True Hollywood Stories — Rick James’ Best Line: “I’m Rick James, b****!”
1. ‘Clayton Bigsby’ Best Line: “Three days ago, he filed for divorce from his wife. When we asked why after 19 years of marriage, he responded, ‘Because she’s a [expletive] lover.'”

Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

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