Dave Chappelle is known as one of the biggest comedians in comedy, but when his show debuted on Comedy Central in 2003, fans didn’t know just how truly genius and groundbreaking he was.

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In  the short span of three-years and 33 episodes, Chappelle and co-writer Neal Brennan made history creating quotable gold and some of the most memorable characters. During the tenure, Chappelle solidified a cult following and laid the foundation for comedy shows including the iconic Key and Peele among many others. In addition to creating a blueprint for shows to come, Chappelle also played a role in ushering Hip-Hop’s biggest names including Kanye West, Yasiin Bey, Talib Kweli and Common to primetime.

In 2017, Dave Chappelle reemerged from his self-imposed exile with new material with his familiar teachable and raw signature style. His most recent Netflix specials, Equanimity & The Bird Revelation, Chappelle ignites the desire for the return of his groundbreaking show as he channels the shows relax format in front of large audiences, as Chappelle unapologetically tackles controversial subjects in a way only he can.


While it seems Chappelle has no plans to bring back his old show, that’s not stopping us from listing some of his most groundbreaking moments.

Check out the Top 10 groundbreaking moments below and let us know your favorites on Twitter @TheSource.

10. Kneehigh Park

The episode featured Dave’s spin on making Sesame Street more realistic, giving kids a real glimpse of life is like as an adult. This episode (clearly aimed at adults) was a comedic way to tackle some tough issues including knowing your status, drug use in the inner cities and economic disparities.

9. The Niggar Family

In the hilarious episode set during segregation, Chappelle utilizes the n-word by adding a comedic twist of literally making “Niggars” white.

8. The Wayne Brady Show

At a time when much of Black America viewed comedian/improv artist Wayne Brady as “corny”, Chappelle showed a side of Brady that many grew to love. Gully Wayne Brady has forever been etched as a staple in television history.

7. The World Series of Dice

Known for his skewed sporting events, the World Series of Dice hilariously brought the corner to ESPN.

6. R. Kelly’s “Piss on You”

At a time when the world was abuzz with theories about the alleged sex tape that featured R&B crooner R. Kelly and a then-underage girl that hit the web, Chappelle took the situation to put his feelings out regarding the legitimacy of the tape in the most comedic way possible-via a music video.

5. The Racial Draft

An episode that was definitely ahead of its time, The Racial Draft hilariously poked jabs at the foul-ups of celebrities by giving us the ability to trade them off to the perceived desire race. We only disagreed with one trade, Wu Tang.

4. Music

With John Mayer and Questlove, Dave tested the preferred musical instruments among Latinos and black people. The show featured an impromptu freestyle which left us all clowning bad freestyles with the classic line, “Boom, pow, surprise.”

3. Charlie Murphy’s True Hollywood Story

Do we REALLY need to explain the impact of this episode?

2. Frontline: The Black White Supremacist

Diving into the subject of race in a way that only Chappelle can, the show introduces the infamous Clayton Bigsby the blind Black White Supremacist that pokes fun at the ignorance of the KKK.

1. I Know Black People

The game show-style episode that featured real New Yorkers and not actors touched on the issue that many African Americans face from white people who think they know the Black culture better than an actual black person. It had to be number one because we finally learned the actual lyrics to the Goodtimes theme song.