The phrase “comedy genius” gets overused. Most comedy shows just play off of the same tired taboo tropes that audiences have become numb to, or resort to fart jokes and clownish antics that have long since gone stale. But Dave Chappelle is often referred to as a comedic genius and one needs to look no further than Chappelle’s Show for proof of his talent.
Chappelle launched his original sketch comedy series in 2003, tapping into the ethos of American identity (particularly Black identity) in the early 2000s. He also teamed up with some amazingly talented celebrities to work with him on various skits, and these people should not go overlooked.
The lyrical artist Ice-T is a living legend in the world of rap, both as an artist and producer. He made a number of appearances on Chappelle’s Show, but probably his funniest cameo was in the skit for “The Playa Haters’ Ball.”
The skit is a nice riff on award shows, as Ice-T commends various people for being horrible human beings (aka haters). Different philosophies of hating are described, while petty insults between the haters serve as proof of their credentials.
9 Wayne Brady
The skit that features Wayne Brady on Chappelle’s Show is so iconic it has become a meme. It opens with the two just enjoying each other’s company as Brady drives his car with Chappelle sitting shotgun. In his warm, upbeat way, Brady talks about the importance of Black celebrities sticking together.
Suddenly, Brady shoots someone outside a club in a drive-by. Dave freaks out, at which point Brady threatens him, fearing the comedian will snitch. Chappelle appeases him, then says he needs to swing by an ATM. But Brady has another solution. He drives up to the corner and has several sex workers give him their money in what is an arguably offensive scene in which he threatens violence.
8 Ron Jeremy
The porn star Ron Jeremy saw his prime come and go long ago. To most people, these days, he is better known as a sexual predator currently in jail, likely for the rest of his life.
However, before his heinous crimes rose to the surface, he did a skit with Dave Chappelle. The skit focuses on Dave visiting the internet, at which points he encounters Jeremy and they discuss the porn star’s career, which apparently, and unfortunately, inspired Dave at a formative age.
7 Rashida Jones
The actress Rashida Jones has established herself in a number of comedy shows over the years, as well as more serious works. She is known as Anne Perkins on Parks and Rec and more recently appeared in the Netflix series BlackAF and Sofia Coppola’s newest film, On the Rocks.
She also appeared in two episodes of Chappelle’s Show. One skit involved the actress signing a contract about what she and Dave would agree to do before having sex – a skit that has somehow simultaneously aged well and poorly, at the same time.
6 Jamie Foxx
Jamie Foxx is a man of many talents. He is an actor, singer, songwriter, and comedian. He starred in the sitcom, The Jamie Foxx Show, and has since appeared in such films as Jarhead, Django Unchained, Annie, and Just Mercy.
Of course, one of his best roles was playing British Prime Minister Tony Blair as part of Chappelle’s “Black Bush” skit. There is something absolutely hilarious about his prim and proper manner of speaking in a formal English accent and he is also completely offensive.
5 Patrice O’Neal
The late great Patrice O’Neal was a radio host and stand-up comedian, Sadly, he struggled with Type 2 Diabetes, which led to him having a fatal stroke in 2o11 at only 41-years-old.
O’Neal played a recurring character in two episodes of Chappelle’s Show. Known as Pitbull, this character was featured in the “Playa Haters Ball” skit, alongside Ice-T.
4 Bill Burr
There is something surreal about seeing Bill Burr in Chappelle’s Show. He has this youthful enthusiasm about him, optimistic and eager, as he plays an announcer in his major appearances.
In “The Racial Draft,” he comments on race and various public figures in a major televised event reminiscent of a sports draft. He also is one of the two announces in “The World Series of Dice,” until the game gets robbed.
3 Joe Rogan
The Joe Rogan Experience is one of the most successful podcasts in the world, with each episode getting millions of listeners. But before launching his podcast, Rogan had a number of other celebrity gigs, including hosting the TV show Fear Factor.
He accompanied Dave Chappelle in a number of skits. The two walked the streets of New York, praising women who had particularly ample cleavage. Another skit involved Chappelle playing a drug addict who took part in Fear Factor, surpassing all the other contestants.
2 Spike Lee
There are few directors who have made such an impact on shaping dialogues around civil rights as Spike Lee. His film Do The Right Thing discussed gentrification in the 80s, while his biopic of Malcolm X brought the civil rights activist’s autobiography to life.
Spike Lee appeared as himself in the season 3 episode, “$55 Million and Getting Revenge,” in which Chappelle became rich and used his money to avenge himself against every person who ever slighted him.
1 The Wu-Tang Clan
The Wu-Tang Clan are arguably one of the greatest and most influential hip-hop groups ever to exist, and getting them on the show was a huge win for Chappelle.
“Wu-Tang Financial” is a skit in which Wu-Tang rappers RZA and GZA open their own financial firm, promoting principles based on the cutthroat economics of the street. Method Man also played himself in various episodes.
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