The Dave Chappelle Story ("8 Mile" Parody)
Inspired by Eminem's underdog film "8 Mile," Dave wondered, "Why couldn't that be me and my story?" So he made one. His stories are a bit more exaggerated, though.
With choruses like "Cash rules everything around me," why wouldn't you want a Wu man watching your money? You've got to protect your neck -- financially speaking, of course. And the Wu-Tang Clan was all about that.
A Moment In The Life Of Lil Jon with Lil Jon
Lil Jon's commitment to shouting a few select ad-libs like "YEAH!," "WHAT?!," and "OKAY!" (alright, those were pretty much the only ones) had many giving their best impression of the King of Crunk. However, only Dave Chappelle could get the real Lil Jon on the phone to have a Lil Jon-off, and the audience was the the true winner.
Roca Pads with Dame Dash
With the rise of rappers founding their own labels, clothing lines, premium liquor lines, and producing other luxury goods, it only made sense that they would branch out into everyday needs. Though few would ever think that Dame Dash and Jay-Z< would put their Roc-A-Fella brand's name on feminine hygiene products. (Note the cameo from Rashida Jones from "Parks and Recreation" before she hit star status.)
Tupac Is Still Alive
In Hip-Hop conspiracy circles, the fact that 2Pac keeps coming out with new records is their main source of evidence he's alive. (The hologram at Coachella probably didn't hurt that case either). But Dave took that to an entirely new level with Nostradamus-like predictions about Blackberries, Grand Theft Auto, and pointing out a girl in the club with a bad outfit. ?uestlove cameos again as a DJ wishing that Pac rest in peace, and he responds "Okay I will!"
R. Kelly "Piss On You" Music Video
While R. Kelly was embroiled in one of the most serious celebrity trials of the 2000s, Dave Chappelle lightened the mood with his ridiculous parody of "Feelin' On Yo Booty," which he not-so-subtly titled "Piss On You." His impression of the Pied Piper of R&B was probably not appreciated by Kellz, but so many more got a good laugh from it.
Making The Band: Diddy
The myth of Diddy is probably closer to his reality than any other superstar. Does that mean that he can fall asleep standing up while bodyguards carry him away or he demands the mother's milk of Cambodian immigrants? We have no way of really knowing, but somehow it's believable.
Dancing For Different Cultures with John Mayer and ?uestlove
Many of the most revered "Chappelle's Show" sketches had to do with putting a mirror up to society and being able to laugh at racial differences. Dave's quest to find out what makes ethnicities dance hit that note exactly, with John Mayer and ?uestlove assisting in his "experiment."
True Hollywood Stories - Prince
Charlie Murphy's stories on "Chappelle's Show" arguably were the most memorable moments in the series' short existence. His tale of how Prince and the Revolution torched his crew on the basketball court -- ending with a monster Prince dunk and the Purple One saying, "Game, Blouses" -- is epic. The best part is that it was true. Well, mostly.
True Hollywood Stories - Rick James
This might be the most popular sketch of the 2000s. Split in three parts, Dave Chappelle's "True Hollywood Stories - Rick James" it took up an entire episode. Dave Chappelle's reimagination of Rick James would make the comedian a household name. Ironically, it would also be one of the things that made him weary of the stratospheric fame. It is among the funniest sketches from the show's entire run, though. So much so that it was reported that Dave would star as the fictionalized Rick James in a feature film, but it was decided it wouldn't happen. Drink up! Be merry!