Dave Chappelle defines comedy in so many ways. We’re not talking about the comic with the most money or active airtime, but we are talking about a comedian who’s respected by any comedian to date. When Kevin Hart was asked by DJ Vlad who was the greatest comedian of all times, he responded:

“Chris Rock and I were at a comedy club and saw Dave Chappelle. We both looked at each other and questioned ourselves… ‘Why aren’t we that funny?’”


When I think about the “Greatest of All Times”, there are a few qualities that come to mind: cultural significance, talent, showmanship, and style. For those of you who remember, the Chappelle Show was THE biggest show on Comedy Central in 2004-2006. He was offered an exorbitant deal and walked away from the hit series.


If you have a chance to look into the man that is Dave Chappelle, you’ll realize why he left the main stream the way he did. He was called crazy for leaving all that money behind, but Chappelle is probably one of the more intellectual comedians we know. He saw something in the show and where his career was headed that took away from who he was and what he believed in.

Chappelle was known for touching on several topics that were closely relatable to his audience such as: race, politics, class, and cross-cultural examination. He didn’t leave a stone unturned when it came to “The People” and their relatability to his work.

Dave also hosted a block party in Brooklyn with artists Erykah Badu, Mos Def, The Roots, Dead Prez, Jill Scott and Kanye West. The film for “Dave Chappelle’s Block Party” was released in 2006, and it grossed over $11 million dollars on a $3 million dollar budget. His close relation to social issues, soul music, and creativity to present it in comical genius has granted him more cultural significance than any comedian in this era.


(Block Party Photo in 2004)


There is no doubt that “Killing them softly” and “For What It’s Worth” were a couple of his best stand-ups and he continues to do stand-up to this day. He hardly makes any television appearances, and he sells out every show that he does.

The demeanor he brings to the stage is almost like an energy he pulls from the crowd. He’s quick-witted, and I’ve rarely seen him unable to maintain crowd momentum – – no matter the size.

With all of this said, I’m adding Dave Chappelle to my G.O.A.T list. He is the greatest comedian of all time.


Katt Williams on Dave Chappelle: