Tareau’s top 15 Chappelle Show skits of all time

Awww yes. It is finally here. What will come in #1? Will Tareau go with the most popular skit? Or will Tareau throw a monkey wrench in your and prevent you to receive your “fix” in your Chappelle Show quest. Tune in now to find out. Please bear with the bad quality on the videos. (Thanks Google.)




15. The Wayne Brady Skit.


This skit was so funny on way to many levels. In the peak of the hip hop era in the early 2000’s, Wayne Brady struggled to achieve acceptance from his Black audience. This skit guaranteed him a seat at ya Grandma’s house at Thanksgiving.



14. Trading Spouses

This one was funny because at the time, Trading Places and Wife Swap, was very popular. Classic Dave Chappelle does this as well. In his variation.



13. Reparations

Yes. This one also a classic due to the hypothetical “what ifs” we as black people ask ourselves everyday. 40 acres and a mule. Also this episode coined the phrase “I’m rich bitch.” Courtesy of Donell Rawlings. Aka Ashy Larry.



12. Dave Chappelle as Lil Jon

Hahahahaha, one of the things celebrities hate is to constantly be bothered with things. Some would argue that this was career suicide for Dave Chappelle but the “Yeaaa” and “whhhaaatttttt” and “oooookkkkkkkaaaayyy” are funnier than shit. His mannerisms as Lil Jon were priceless as well.



11. Tyrone Biggum on Fear Factor.

“Gotta Play to win!” Hahahahahahahahah Tyrone Biggum actually caused a racial stir with me. I was him for Halloween one year and (not to compare myself to Dave Chappelle) I kinda felt what Dave was talking about with the “Black Pixie” skit. Nonetheless I thought it was funny because I could literally throw a rock from where I am sitting and hit several Tyrones. Sad but truth. Sadness does have its comedy, right.


 10. R. Kelly Piss On You

Dave does not get enough credit for his bravery, folks. You see this was a genius skit due to R. Kelly peeing on an underage girl. The Black community is so forgiving too a fault but Dave reminded all those people who got back to bumping and grinding that R.Kelly is a pedophile and he should be made fun of. Nuff said. DRIP DRIP DRIP. HAHAHAHAAHAHAHAH


9. The Mad Real World

“Get my money, Kyree” hahahahahahaha. Dave, like many Black Americans, often wondered what it would be like if MTV had an all Black Cast for their hit TV show ‘The Real World.’ You see ladies and gentlemen, those shows would always pick a Black person who is not “A Hood” black person and they would get eaten alive by their all white cast mates. Lol Dave flipped the script and history was mad.


8. Dave gets revenge.

A lot of people didn’t find this skit funny. I loved it however. Especially when Dave looks at the camera and says “How Lucrative” The lost season was not as popular as season 2, but who cares. Laughter heals y’all.


7. Rick James

E! True Hollywood story presents Carlie Murphy.  RIP Rick James. Everyone loves these and I’m no different. Probably responsible for Chappelle Show superstardom, Charlie Murphy’s Career also skyrocketed. White People were no longer scared to cast him in other roles.  “Fuck yo couch.”


6. Prince Vs. Charlie Murphy

Game! Blouses! RIP Prince.



5. Who knows Black People

This show was a great look at how the majority of Black People thinks about pop culture and surrounding issues. I even learned what that disputed Good Times jingle was “Hanging In The Chow Line.” Classic right? But so is this whole segment =)



4. The NIGGAR Family

LMFAO Just watch! No explanation needed.




3. The Controversial Pixie Edipsode

Hahahahahahaah. “Look at all that meat.” Controversy or not, this was some funny comedy.


2. The Racial Draft.

This is probably everyone’s favorite skit due to the uniformity that was exhibited. Mos Def played the prototypical old skool brotha. Very Mature Rondell.


#1. 2 way tie. The Haters Ball & Clayton Bigsby

No explanation needed. Just watch. RIP to Patrice O’Neal.

So there we have it. Another day another list. Another sip of Safeway’s Tea with a twist. Stay thirsty my friends




  1. Love this! The Wayne Brady one will always be one of my faves…that and Charlie Murphy and Prince…”you know where you got that shirt from, and it damn sure wasn’t the men’s department…”
    Great Top 15!

    Liked by 2 people

  2. Lmao! Great list! I definitely agree! I am a huge Prince fan – so that skit was hilarious to me! All of these were pure gold lol.

    I would add the 2pac skit, and the one where he had the camera and he could see people’s inner thoughts lmao!

    Liked by 1 person

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