Top Ten Dave Chappelle Bits

Dave Chappelle is a testament to the fact that good guys can sometimes finish strong – if not quite first. Here is a guy who after years of trying to carve out a name for himself in show business only to watch peers (like Chris Rock, Chris Tucker and Martin Lawrence) accelerate past him, finally got his big break in 2002 when Comedy Central gave him his own show. After two years of groundbreaking success with The Chappelle Show, he made a decision that would not only affect his reputation but would have serious repercussions on the career he had worked years to build. He left halfway through shooting season 3, effectively putting the show on permanent hiatus and denying Comedy Central their highest rated show after South Park. He also walked away from his $50 million contract. Did the 19 hour workdays finally take their toll? Did he not like the direction his show was taking? Till this day Chappelle has refused to conclusively state what caused his departure.

Not that it matters anymore. Chappelle has always had the comfort of the stage to fall back on. From the first time he picked up a mic as a 14 year old, he’s constantly performed for audiences all over the world and gotten a reputation for been one of the most gifted comedians of his generation. Even the great Richard Pryor once dubbed him his true successor. So instead of moping and feeling sorry for himself, he started working the stage again, hitting up different locations all over the country. This culminated in a $60 million Netflix deal for three stand up specials in 2016. Since then he’s only done more specials, won Grammy and Emmy awards and received the prestigious Mark Twain Prize for American Humor in 2019. Not bad for a guy who was deemed crazy and mentally unstable just ten years ago. This list should be seen as more than just a selection of some of his greatest stand up bits over the span of his 30 year career, but a testament to one of the great comic talents of his generation.

Ten

Kneeling During National Anthem

The Bird Revelation (2017)

Dave has never shied away from discussing race or racism in his material like some of his contemporaries. As such, it was a given that he’d have an opinion on the heavily publicized decision by some black athletes to kneel during the national anthem in protest of police shootings. It’s a short clip – not lasting up to a minute – but it’s enough time for him to blissfully mock white outrage.

Nine

Mickey Mouse (2004)

After season 2 of Chappelle’s Show, Dave decided to go on tour for the first time in four years. The tour culminated in his third stand-up special, For What It’s Worth, where he delved into different topics including the impact his new-found fame his hit show was having on him. Although by the time of his special this bit had been almost completely modified, this clip is from one of his tour stops where he joked about an unforgettable encounter with Mickey Mouse. Yes. The Mickey Mouse.

Eight

White friend, Chip

Killin’ Em Softly (2000)

One of the unmistakable realities of life in America – especially as it pertains to race – is white privilege. It is an unfortunate fact that white Americans are economically and judicially favored over minorities. Chappelle illustrates this perfectly when he tells a joke about his white friend, Chip, and the privileges he enjoys just by being in his company.

Seven

Jails/Police

HBO Half-Hour (1997)

Dave opened his first half-hour special in San Francisco with pointed social commentary about racist police. Pretty heavy, right? Not with Mr. Chappelle. He first puts his audience at ease by complimenting their city before quickly pivoting and addressing the racial bias police officers have for black people. It’s handled with remarkable skill and impeccable timing.

Six

Native Americans

For What Its Worth (2004)

When one jokes about a topic as much as Chappelle does about race, it’s important to keep one’s approach as fresh as possible. He has a way of keeping his audiences guessing and subverting their expectations. This was evident here when he tells a story of running into a Native American and the adventures he had learning about his customs. Did it really happen? Most likely not, but for the way Chappelle plays with the audience’s expectations it has to go down as one of his smartest, funniest bits.

Five

Michael Jackson

For What Its Worth (2004)

Jokes about Michael Jackson’s trial had become increasingly commonplace between 2004 and 2005. It provided plenty of fodder for stand-up comedians and late night hosts at the time. So when Chappelle joked about the legendary musician, he had the challenge of bringing something inspired from a well-worn topic. Challenge accepted, challenge completed.

Four

Jussee Smollet

Sticks and Stones (2019)

Even if you didn’t follow what happened with Empire actor, Jussee Smollet early this year, chances are you heard his name. Unfortunately for the now infamous actor, much like Ja Rule, he is destined to be immortalized in popular culture as ‘Juicy’ Smollet based on this Chappelle bit. In classic Chappelle style, he breaks down the strangeness of the incident simply and with no little skill.

Three

Terrorists Don’t Take Black Hostages

Killin’ Em Softly (2000)

Racial bias has always featured heavily in Chappelle’s comedy and he’s often pointed (with great humor) the ways institutionalized racism affects minorities. But in this brilliant bit from arguably his finest stand-up performance, he points out that sometimes racism can benefit black people.

Two

Bus Hostage

For What It’s Worth (2004)

Pryor once deemed Chappelle his one true successor to the comedy throne. Even though it’s still too soon to crown Chappelle as the new king of comedy or whatever, bits like this show that Pryor’s assessment wasn’t far off. Using storytelling techniques reminiscent of the great man, Chappelle details an unfortunate run in he had with a homeless man in a public bus.

One

3am in the Ghetto

Killin’ Em Softly (2000)

The bit that made me a Chappelle fan. This bit is not just about the funniest thing Chappelle has done till date, its underlying brilliance is subtle but undeniable. On the surface it’s just a funny joke about a negative experience he had in a ghetto, but if one looks deeper they would see Chappelle’s patented brand of social commentary is at play. Sure, he’s making you laugh but he’s also encouraging you to think. It’s the genius of Dave Chappelle, one of the greatest living comics.

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