The Best Chappelle Show Episodes According To IMDB

Many comedians have hosted their own television shows over the years, but few have had quite the same cultural impact as Chappelle's Show. First airing on Comedy Central in 2003, host and co-creator Dave Chappelle gave audiences a late-night show that combines stand-up monologues with sketch comedy, wrapped in hilarious and thought-provoking commentary on topics including drugs, racism, pop culture, and more. A third season was planned, but never materialized: Laid low by stress, creative differences, and the fact that some people were laughing at the wrong jokes, Chappelle quit the show. Eventually, Comedy Central released "The Lost Episodes" in 2006. These three episodes contain previously unreleased sketches, and are co-hosted by Charlie Murphy and Donnell Rawlings, who had already made frequent appearances on the show prior to this point.

With the entire series now available to stream on Netflix and HBO Max, we're here to take a look at the 12 best Chappelle's Show episodes, according to IMDb. Each of these episodes has a user score of 8.2 or higher, and episodes with the same score are ranked in order of release.

This episode marks the first appearance of Chappelle's iconic impersonation of crunk rapper Lil Jon. He appears in not one, but two sketches as this character. The first "Moment in the Life of Lil Jon" sketch revolves around Chappelle's Lil Jon as he attempts to make flight reservations. The second sees a television host named Teresa Roddy interview him for her television program. 

Chappelle introduces another popular reoccurring segment in this episode: "When Keeping It Real Goes Wrong." In this sketch, Chappelle's Darius James confronts a man at a club who tells his girlfriend, "It was good seeing ya." What Darius does not realize, however, is that the man in question is a 10th-degree blackbelt who started trouble just so he can practice his karate and street-fighting strategy. The beatdown that follows is so embarrassing, even Darius' girlfriend joins in on the action. Ouch!

In the monologue preceding "Celebrity Jury Duty Selection," Chappelle talks about the discussion he and co-creator Neal Brennan have whenever a Black celebrity is in trouble. According to Brennan, Chappelle never believes that a Black celebrity is guilty, which Chappelle humorously admits is true. "To me, it's always about reasonable doubt," Chappelle says. "What's reasonable doubt to a white person, you know, might not be reasonable doubt to a Black person." Chappelle subsequently shows what would happen if he was part of the jury for the cases of O.J. Simpson, Michael Jackson, and R. Kelly, the latter of whom he has already poked fun at on the show. Even though the sketch is not meant to be taken seriously, Chappelle does bring up some interesting points about the justice system, including how Biggie and Tupac's murderers were never found, but the police arrested O.J. Simpson the day after the crime he was accused of.

This episode features top-notch sketches such as "The Dave Chappelle Story" and "Ask a Gay Dude," yet many fans will most likely recognize it for the iconic two-part sketch, "The Mad Real World."

The sketch was inspired by Chappelle's attempt to help childhood friend and fellow comedian David Edwards find success by landing a role on the MTV reality show The Real World. After a joke with one of his white female co-stars was taken the wrong way, Edwards infamously became the first person to be evicted. Chappelle, of course, was not too happy about it.

Chappelle explains in the preceding monologue that "The Mad Real World" illustrates what would happen if "we put a white guy around six of the craziest Black people we could find." While some viewers might feel bad for the white character, Chad, the sketch is unforgettable. Things get especially pointed when Chad's ex-con co-star Tyree stabs Chad's father after he looks at a female co-star the wrong way.

This episode's most infamous sketch is an example of just how fearless Chappelle is when it comes to writing biting social satire. The sketch in question is none other than "The N***** Family." This sketch parodies black and white sitcoms of the 1950s, and revolves around a suburban white family with a last name that happens to be a certain racial slur. The purpose of this sketch is to satirize white people's flagrant use of the slur in question, but what makes it one of Chappelle's best sketches is its unabashed self-awareness. Squirm-inducing lines and scenarios are packed in here, forcing audiences to confront societal realities as they laugh, shudder, and gasp. Chappelle is at his most sharp in this sketch: His comedy is unflinching and his criticism has none of its cutting edges sanded down. He balances on a knife's edge between clear-eyed satire and absurdist humor, and somehow, he makes it look easy.

The series premiere of Chappelle's Show hits the ground running with sketches such as "PopCopy" and Chappelle's very own Mitsubishi Eclipse commercial. Yet the most talked-about sketch from this episode is the last: "Frontline: Clayton Bigsby." This spoof of the popular PBS docuseries Frontline sees host Kent Wallace interview Chappelle's Black white supremacist character Clayton Bigsby, a reclusive blind man who has spent his whole life believing that he is white and, as a result, has become a hero to white supremacists across the country.

Chappelle uses this sketch to prove just how idiotic racism is. One of the funniest moments from this sketch occurs when Bigsby's white supremacist buddies drive him to a signing of his many books. On the way there, Bigsby's ride pulls up beside a car full of white people that is blasting rap music out their speakers, which prompts Bigsby to call them a racial slur. The driver asks, "Did he just call us n*****s?" Then: "Awesome!" 

The last Chappelle's Show episode on this list is famous for a lot of reasons. Chief among them is the fact that it introduced fans to the iconic catchphrase, "I'm Rick James, b****!"

In the vein of E!'s popular docuseries True Hollywood Stories, Charlie Murphy recounts his crazy history with "Super Freak" singer Rick James through "dramatic reenactments," in which Chappelle gives a legendary performance as James. Meanwhile, the real-life Rick James, who died six months after this segment aired, comes in to give his side of the story, which only heightens the comedic genius of the segment. This sketch went on to become so beloved that it renewed interest in James' music. On the flip side, this sketch also lead to fans running up to Chappelle on the street, just so they could quote his "Rick James" catchphrase to him –  sometimes in front of his children.