
A confession: during Chappelle's Show initial run in 2003-2004, I always fast-forwarded past the musical performances. Here was Josh's mindset at the time: no Eminem, no care. Just awful. I was a dumb kid from the country who wasn't yet aware of the brilliance of Killer Mike and the Roots, and it wasn't until 2006, coincidentally when Chappelle's mediocre season three aired, that I began to appreciate Nas rapping in a car.
It's been a decade since Chappelle's Show first premiered on Comedy Central, and while the sketches themselves have been widely dissected and bracketed (rightly so), far less attention has been paid to the rappers Chappelle booked over the first 25 episodes, spanning seasons one and two. This past Sunday, March 3rd, was the nine-year anniversary of Kanye West's first major TV appearance, when he performed with Common during the "World Series of Dice" episode, so we thought we'd take a look back at some of Chappelle's Show greatest non-sketch music performances. Sorry, "Dancing for Different Cultures" and "Wu-Tang Financial." You're #1 in my heart.
Artist: Nas
Song: "Close Edge"
Episode: "1.1"
Artist: GZA
Song: "Knock Knock"
Episode: "1.10"
Artist: The Roots
Song: "Hardware"
Episode: "1.9"
Artist: Talib Kweli ft. John Legend
Song: "Around My Way"
Episode: "Music Jump-Off"
Artist: Killer Mike
Song: "Akshon (Yeah!)"
Episode: "1.7"
Chapelle's Show: Black Star Music Video from Jared Morgan on Vimeo.
Artist: Black Star
Song: "What's Beef"
Episode: "1.12"
Artist: Big Boi
Song: "The Rooster"
Episode: "2.13"
Kanye and Common on the Dave Chapelle Show from Derek Blair on Vimeo.
Artist: Common and Kanye West
Song: "The Food"
Episode: "2.7"



#2 is the artist formerly known as Mos Def aka Yasiin Bey
Also your first paragraph should say Mos Def rapping in a car.
Yeah, mistakes happen and all that, but twice?
Since Mos Def passed the name Mos Def to Stephen Colbert, does that mean #2 is really Stephen Colbert rapping in a car?
Was thinking the same thing on Mos Def, who by the way was awesome in Yo Gabba Gabba as “Super Mr Superhero”
After his appearance on the Report, I suspect that Colbert might secretly be Dicknose Franco.
Now I got Colbert doing Black Star and BOBS verses stuck in my head…
MOS DEF is not NAS and yeah they don’t look alike either.
But if Nas was dropping BOBS in ’99, does that mean Nastrudamus didn’t’ happen? Because I’d be OK with this.
No DMX on the list? WHAT!
No Kanye, Mos Def and Freeway either.
Yeah, the Two Words snub sticks out. The Food? For real?
The first thoughts I had before clicking were “Two Words”, “What’s Beef?” and Yasiin Bey/Mos Def rapping in a car.
The Food was so good that Com rushed it onto his album. So yeah, that counts.
I’d put up the unaired Beastie Boys performance ‘cuz it was “hella fresh,” as the kids say
Didn’t TSS share that when Adam died? That was a great performance.
First thing I thought of.
The worst one was an uninspired Ludacris closing out the Rick James episode. Should’ve been you, Common.
How can you mix up Mos Def for Nas twice?? Especially when the title of the freaking video says Mos Def. O____O
I just fast-forwarded past all the music. No funny = don’t care. I’m still okay with that.
Yeah, same for me with SNL. I watch comedy shows for comedy not music.
“You forgot John Mayer.” said none one.
no one*
Where the hell is DMX?!?!?!
Mos Def’s closed edge was the absolute best. De La Soul was pretty damn good too
” The Food ” is clearly the greatest in-show sitcom performance of all time.. any other performance posted here is just completely uncivilized..
… side bar:::
Be in 2005 was a flawless piece of work and shall be Timeless for decades to come.
Holy shit Questlove is skinny
How can you have any credibility when you mix up Nas and Mos Def? You even tagged Nas in the post… Do you watch that video and think it sounds or looks like Nas? No offense, Josh, but that’s bush.
And leaving DMX off this list is criminal. Dave just kept queuing up new songs and DMX kept going and going.
I’m the whitest white guy who ever whited, and even I was screaming “Mos Def, mafa!”
The Music Jump-Off episode was absolute brilliance and it sucks that it wasn’t included in any of the dvd releases.
The greatest part of “The Food” is that Common used that version for the album release
After calling Mos Def Nas, you should have messed up all the names and called it humor. I would have laughed.