The 10 Funniest Skits in the Much-Too-Brief History of Chappelle’s Show

In the Midwest, we argue about a lot of things when it comes to sports.

White Sox-Cubs. Cubs-Cardinals. Indiana-Purdue. Ohio State-Michigan. Notre Dame-everyone else. I could go on and on and on.

While most of it is good natured, there are strict battle lines drawn and most Midwestern sports fans staunchly support their teams and viewpoints, with little bend and rarely any break; but despite this polarization of opinion when it comes to sports, there are some things that are universally agreed upon.

Today, I decided to step outside of the sports world to celebrate something that, in my experience, is beloved and appreciated by all Midwesterners – at least the ones that I know.

That something is Chappelle’s Show, hosted by the great Dave Chappelle.

And seeing as how Chappelle now proudly makes his home in Ohio, well, he’s one of us.

The idea for this post actually struck me this weekend when I was showing my brother some of my favorite Chappelle’s Show skits online. I realized that there were only two seasons of this magnificently funny show, but damn did Dave pack a lot of brilliant humor into those two seasons.

It’s unfortunate that production and personal issues frustrated Dave enough that he left during Season 3, but from all accounts he seems happier no longer doing the show; if that’s the case, then good for him. We’ll always have his stand-up, plus the greatest two-season archive in comedy history to to enjoy in perpetuity.

So let’s do just that.

Here is my personal Top 10 list of Chappelle’s Show skits. I’m sure mine will probably differ from yours, so feel free to go here and find what you feel I’ve missed and drop a link in the comment section.

1. Racial Draft

This is the first Chappelle’s Show skit I ever saw, and needless to say I was hooked. Absolutely brilliant.

2. Frontline – Clayton Bigsby Parts I & II

Many, many people have lauded Chappelle for being able to provide astute social commentary through the biting honesty of his comedy. I won’t belabor those points here, but I obviously agree. These two skits are the most impressive examples.

3 – Better in Slow Motion

I don’t know why exactly, but I laugh my ass off at the end of this skit every time.

4- True Hollywood Stories – Rick James Parts I & II

This is perhaps the most famous and oft-quoted skit from Chappelle’s Show. Watch it, bitch.

5 – Trading Spouses

Few aspects of Chappelle’s Show make me laugh as mucha as when Dave Chappelle impersonates a white guy. The brilliance of this skit is a) the idea, and then b) how brilliantly it is executed. Sure, it takes stereotypes to the extreme, but do you really think it would be all that different if they did this in real life?

6 – Tyrone Biggums Fear Factor

All of the Tyrone Biggums skits are funny, but I liked this one of the best because I thought it was the most clever.

7 – Reparations 2003

Another skit with Dave impersonating a white guy. Money.

8 – Samuel L. Jackson Beer

It’s get you drunk! Pay special attention at the end when Dave (as Sam Jackson) dives mouth first into the bowl of peanuts and takes a huge mouthful. I don’t know why, but this gets me every time.

9 – The Wayne Brady Show

I think this skit is somewhat overrated because it drags a bit, but the idea is brilliant and both Brady and Chappelle are hilarious.

10 – R. Kelly “Piss on You” Music Video and Remix

Nothing really to say about this one. R. Kelly’s career hasn’t been the same since the trial and this video.

Honorable Mention:

The Playa Hater’s Ball

Black Bush

Update: How could I forget this one!? Probably because I didn’t find it while scrolling through the Comedy Central video archive of Chappelle’s Show, but I might have just missed it. Either way, this one is a classic:

I wrote this song a long TIIIIME ago!

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