There is only one Dave Chappelle, and his skits have become legendary over the years.
Here’s a look at 7 of his most memorable skits that will most certainly bring you back to the early 2000s and get you laughing.
7. “Making the Band”
Season 2, Episode 10
Original Air Date: April 7, 2004
Chappelle was a follower of various MTV shows, and this is obvious in his comedic takes on the network.
This comedy sketch was an all-out parody on Diddy’s Making The Band and it mocks some of the over the top demands from its music mogul.
It is a fun time capsule into reality television from the early part of the 2000s and is still relevant today.
In a show full of hip hop performances, Chappelle’s Diddy impression is spot on and the segment is memorable for that alone.
6. “The Wayne Brady Show”
Season 2, Episode 12
Air Date: April 7, 2004
This segment spawned one of the show’s most quoted lines “Is Wayne Brady going to have to choke a bitch?” and pokes fun at Chappelle himself for calling Brady soft along with Brady’s image as portrayed through the media.
Chappelle and Brady are in a Training Day type parody and are put in dangerous situations.
It is also a notable instance of someone besides Chappelle really taking over the skit to the benefit of everyone watching.
5. “Frontline—Clayton Bigsby”
Season 1, Episode 1
Air Date: January 22, 2003
Chappelle had a lot to say in his inaugural episode, and this is the best of the best.
This was the show’s first real groundbreaking moment in terms of discussing race, as Chappelle’s Black-White Supremacist known as Clayton Bigsby is a true indicator of where the show would go during its run.
The framework of the segment itself, as a nightly news story, is hilarious as Bigsby is a seemingly hilarious oxymoron.
The undertones of the segment of mocking the Ku Klux Klan is also relevant and something Chappelle certainly had in mind as a way to kick off the show’s run.
4. “Reparations”
Season 1, Episode 4
Air Date: February 12, 2003
Chappelle’s “Reparations” sketch is hilarious in its take on how Black people would actually use their money if they were awarded reparations.
Of course, this was fairly controversial at the time and still is, but it is coming from Chappelle’s hilarious comedic perspective and it looks at how some businesses would change were reparations to ever occur. Chappelle uses a news format again effectively to “cover” the change.
3. “Charlie Murphy’s True Hollywood Stories: Prince”
Season 2, Episode 5
Air Date: February 18, 2004
Now we are getting into the truly quotable segments. This hilarious take on a day in the life of the late Charlie Murphy and the late Prince is an unforgettable one.
“Game. Blouses.” and the entire idea of Prince feeding his opponents pancakes is too ridiculous to not laugh at, while Chappelle does a hilarious impression of the Purple One throughout.
This segment is near flawless in its execution too, as it mocks E! True Hollywood Story and its format the entire time.
2. “Charlie Murphy’s True Hollywood Stories: Rick James”
Season 2, Episode 4
Air Date: February 11, 2004
Another of Chappelle’s E! True Hollywood Story parodies, is the one featuring the late Rick James, who actually appeared in the segment making fun of himself.
Chappelle, of course, plays James at his prime, and it again pits him with Charlie Murphy for various shenanigans throughout.
This was the segment featuring “I’m Rick James, Bitch!” and “Fuck Your Couch” among other quotable lines.
Chappelle even dons James’ trademark dreadlocks and goes all out in his portrayal of the funk icon.
It also pokes fun at Eddie Murphy and the rock star life in general in a slightly different way than the Prince sketch does.
1. “Mad Real World”
Season 1, Episode 6
Air Date: Feb. 26, 2003
Chappelle brings out a wide cast of characters in his best sketch ever. Chappelle himself plays “Tron”, and this is of course another parody of MTV’s very popular The Real World.
It’s the basic premise to flip the switch on the reality show and have the cast be mostly Black is amusing and it does send a deeper message beyond just being funny.
The extreme differences between five black inner-city roommates and the straight-laced white man, Chad, is played to perfection.
Chappelle is also saying in his own way that there are serious racial disparities in the world of reality TV and in the media in general.
The use of black and white imagery is perfect too when it is used. If you’ve seen it, you won’t forget it anytime soon.
