Dave Chappelle is a major force in the comedy world and it has been that way for decades. Making waves in the 2000's for turning down upwards of $50 million dollars because he wouldn't have full creative control of his show upon renewal, many thought that he made the wrong call at the time.
Coming back years later with so much new material, a very clear perspective, and advice on what to do in similar circumstances gave many an idea of where his head was at, he did not care about what fans thought. He made his show the way he wanted and when he felt like it was going to be taken away from him he left, so here are some skits you may have forgotten from one of the greatest sketch comedy shows of all time.
Samuel Jackson Beer
This sketch is one of the many where Dave does an impression that is not spot on but still works because of how well crafted it is in the execution of the idea. Three men sit for a meal at a restaurant and each orders a drink with the second man ordering a Samuel Adams. When it gets to the third man played by fellow stand-up Bill Burr he orders a Samuel Jackson, immediately cutting to a yelling Sam Jackson played by Chappelle dressed similarly to Samuel Adams.
Inside The Internet
The premise here is simple, Dave wonders what it would be like to go inside the internet.
Starting off by walking inside looking for the score to the Knicks game, Dave winds up getting distracted by human pop-ups. He gets himself a bag full of illegally ed music as well as being catfished. Getting himself a guide in Ron Jeremy who keeps offering to let him watch some dirty movies to which he says he is not interested.
The Mad Real World
Dave thinks about how "The Real World" always seems to put just one black guy on the show to make them look crazy, saying that one white guy surrounded by only black people would come off the same way. The sketch that follows is one of the funniest in the shows history to most die-hard fans, starring Charlie Murphy and Donnell Rawlings as well as Chappelle. Using the same horrible editing techniques the show it is mocking does and having the houseguests work at a juice bar makes for great comedy.
World Series Of Dice
Made to mock the ridiculousness of airing poker on television, which Dave sees as something not serious enough to be on ESPN at all. Introducing the skit as the equivalent to something that would entertain black people, this is another one with regulars Donnell Rawlings, Charlie Murphy, Bill Burr, and the addition of Eddie Griffin as "skilled" dice player Grits 'n Gravy. The skit is not only hilarious but also introduced a fan favorite character of Donnell Rawlings, as "Ashy Larry" is an often brought up character when speaking about the comedian.
"Special" Law & Order
This sketch, like a lot of Dave's, is actually saying something very powerful under the surface. Dave and his writing partner, Neal Brennan, being a writing duo of white and black gave them the ability to tackle two different perspectives and make sure that it was not just controversial for the sake of controversy.
A sketch that shows what it would be like if the justice system worked the same way for CEO's as it did for common young black men and vice versa. It is extremely funny and yet when you take a step back it makes you think, just like a lot of Dave Chappelle's jokes do.
The Playa Haters Ball
A classic sketch that stars a who's who of cast in the most colorful wardrobe you could possibly think of. Presented as a sort of roast for pimps, this skit is very funny and showcased the comedic talents of everyone involved in it. Fans loved it so much it even spawned a sequel sketch where the Playa's traveled back in time.
Popcopy
Dave imagines a copy service that treats their customers like total garbage in this sketch that pushes the boundaries of what he could get away with. Dave started most weeks by saying something like "Well, I am not cancelled yet." So he was always trying to push forward what was allowed on cable TV, and this skit definitely let him get away with a lot. Starring Michael Rapaport and fellow Half Baked star Guillermo Diaz, this skit is not one to be missed, so if you have not seen it then go look it up.
Charlie Murphy's True Hollywood Stories: Prince
Often lost in the fray due to how famous the Rick James sketch became and still is. The Prince story is just as funny if not funnier, and fans know that it comes down to the delivery of Charlie Murphy when telling the stories.
The story that is told here is arguably much funnier because it is way more surprising than the Rick James stories are. What happened to Charlie and his friends at the hands of Prince is just down right EMBARRASSING and all fans can agree on that point.
White People Can Dance (W/ John Mayer)
Suggesting that the myth of white people not being able to dance is completely untrue, Dave says you just need the right music. Recruiting John Mayer to play the guitar in various places, he shows the world that white people can dance given the right tools. Repeating the process with latino people and black people and adding instruments as necessary. It is a very funny skit and John has some really great comedic timing that was unexpected to most viewers.
Racial Draft
This is a very iconic skit that many die-hard fans probably have not forgotten about, but there are some people that have, so it needed to be here. The premise is very simple, many people like Tiger Woods and Halle Berry are often argued about in private of course where their talent comes from, which race that is. So there must be a racial draft, it is the only way to settle all of this in Dave's mind.