What Is The Greatest 'Chappelle's Show' Skit Of All Time?

After over a decade out of the spotlight, the world’s best comic is finally making a return to the stage.
After two seasons of shifting the cultural zeitgeist and cementing his status as one of the world’s elite comedic minds with Chappelle’s Show, Dave Chappelle famously walked away from a $50 million contract with Comedy Central. And just like that, a modern-day living legend, who was widely considered the world’s best stand-up comic, was gone.
Hurricane Katrina came and went, and the world never knew what Chappelle thought about it, or more importantly, what he thought about his friend Kanye West saying “George Bush doesn’t like black people.” Barack Obama became the first African-American president in the history of the United States and Chappelle was nowhere to be found. How about Trayvon Martin? Chappelle walked away from the world, and all we were left with for the next decade was the thought, ‘What would Dave Chappelle think about this?’ And for a while, it seemed as thought he would be gone forever.
But then, in 2013, like a phoenix rising from the ashes of his television career, Dave Chappelle returned.
First, with a 10-show run at Radio City Music Hall, followed by a couple appearances on late night television, and then the return of Dave Chappelle had officially begun.
Then, almost as if it were always meant to be this way, Dave Chappelle stamped his ticket back into the hearts and minds of the mainstream on November 12, 2016 — the night he hosted Saturday Night Live.


Donald Trump had just shocked the American public with one of the most unlikely election results and uncertainty was sweeping the nation.
Going into the night, expectations were high. The country had just lived through a week unlike any it has ever seen, and the reclusive Dave Chappelle was lined up as the host. You had the perfect storm of comedy, so the only question was whether SNL and Chappelle would be able to deliver. And he did. Of course, he did.
Chappelle dropped a line about the horrific Pulse Night Club shooting and the Wu Tang Clan, as only Dave Chappelle could and just like that, he was back. 10 years and 40 pounds of muscle later, and Dave Chappelle was back.
The Monday after Chappelle’s SNL episode, I came into work and wrote this article:
Apparently, the answer was $60 million dollars.
Just one week after his electric return on Saturday Night Live, a deal between Chappelle and Netflix had been announced: 3 stand-ups for $60 million dollars. Dave Chappelle finally got the big money he always deserved, and this time, it was on his terms.
The first two stand-up specials, which were previously recorded, premiere on Netflix on March 21, 2017. Titled The Age of Spin and Deep In The Heart Of Texas, both hours prove that despite his time away from the limelight, Dave Chappelle is still the undisputed king of comedy.
So it got us thinking, as so many of us have thought many times before: What is the greatest Chappelle’s Show skit of all time?
Spoiler Alert: This list is a personal opinion, so, no, Rick James is not the #1 one sketch.

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